The pocket square, or handkerchief, is an interesting indicator of how dapper clothing has trended in the past 15 years.
Broadly speaking, the late 1990s were all about business casual and the dotcom boom. Silicon Valley was not concerned with dressing up. That began to change around 2003/4, after the recession, with those out of work perhaps more concerned with appearing professional. (Sales of tailoring jumped 24% that year in the US.)
Interest in handkerchiefs grew too, and when Thom Browne and Tom Ford launched tailoring lines a few years later, both were heavily pocket squared.
It was still a niche accessory, however: it took the launch of Mad Men in 2007 for the handkerchief to go mainstream. That was when every salesman in every office started wearing one.
US Esquire wrote a nice piece about this trend back in 2015, using Google search data. Back then they could see some men being turned off by them, saying the pocket square had become too ubiquitous. But they also noted that they had never been more popular in cheaper, mainstream shops.
Five years later, the same data shows a clear dropping off in interest, albeit a slow one. Below is a graph showing indexed use of the search term globally.
It seems intuitive that fashionistas would have been the first to adopt the look, and then the first to drop it when it became too common. And that mainstream consumers might hold onto it longer.
But how about menswear enthusiasts? It feels like they might be both early adopters and laggards as well. After all, this is precious piece of traditionalism that was suddenly wearable.
That’s certainly been my experience, and what I’ve seen around the industry generally. There was a slight reaction against the pocket square a few years ago, perhaps when it reached peak popularity. But men into tailoring have largely held onto it until recently.
I began to wear a pocket square less about a year ago.
This is a shame in some ways. As ties become less common, and are seen as a sign of dressing up, a pocket square can be a nice replacement. Michael Bastian, commenting on the growing trend, called the pocket square ‘the new tie’ way back in 2005.
It also deprives men of a way to express themselves with bright colour, and pattern. Without the handkerchief or tie, few men will have any way to justify wearing printed silks.
But it doesn’t sadden me.
First, because when you’ve been into menswear for a while, I think you learn to accept such trends. If you want to appear in any way relevant - and not 'period' - you need some awareness of cultural norms.
Clothing is a language and language is social.
Second, I know from experience that trends do not mean that you have to give up everything. You just move more slowly.
Savile Row tailors used to talk about how lapel widths have varied over the decades. As fashion brands fluctuate from 1 inch to 6, a tailor might move between 3 inches and 4.
In the same way, I won’t stop wearing a pocket square. It was not a trend for me, and I won’t drop it like a trend. I will just wear it more narrowly.
For example, I will continue to wear it on formal occasions. With a suit and tie at a very smart event, certainly, and perhaps adding a white linen to a jacket for a local dinner.
It will also continue to be part of my wardrobe more generally, considered in the same way as a colourful scarf or sleeveless cardigan: no longer the default, but always an interesting option.
So I might wear a muddy little paisley with a tweed jacket, just because the colours go so well; or a red bandana style because I think it complements the western shirt underneath.
Those squares might be less showy than in the past, but then I never liked very strong patterns or bright silks anyway.
I've also found myself doing a few things to compensate for the lack of a handkerchief.
The first is carrying a favourite pen or pencil in the outbreast pocket.
I usually carry one anyway, and it’s nice to display ones I love like Yard-O-Led silver (above), Dupont lacquer or the 'Perfect Pencil' from Faber-Castell.
I also like the fact that, like the best menswear, it’s obviously practical. I get it out, use it, and put it back, unlike a handkerchief.
The other thing is occasionally wearing a badge or pin.
This was inspired by a friend that often wears old pins on his workwear, but it also reminds me of being a teenager, when my jacket would be full of badges of bands I was into.
A badge is more akin to a handkerchief in terms of colour and decoration than a pen. And it's more unusual and personal: an opportunity to display something you believe in, or are passionate about.
This is completely unrelated to menswear, but I personally think people in the UK don’t talk enough about things they believe in. And if they’re going to wear a logo, I’d much rather it was a musician or a museum, rather than Supreme or Nike.
The only problem with a pin is you can only wear it on more robust or open-weave jackets without damaging the material. So it’s limited to tweeds and some linens and cottons.
Finally, I find I'm bolder elsewhere - particularly with shirts.
I’m sure the lack of tie or handkerchief is a reason awning stripes (above) have become more popular recently. And I personally wear more unusual colours like red and green than I would have previously.
The Zizolfi tweed jacket below would look a lot more boring worn with just a plain shirt.
The only danger is that this assumes the jacket is kept on. It's worth keeping in mind what the shirt will look like when the jacket is taken off as well.
I’m sure the pocket square will make a re-emergence at some point.
While the trend of the past century is inexorable casualisation, this is a shorter-term, 15-year swing, which will probably sway back.
For the moment, embrace the idea of change, and potential for new ideas.
No clothing or style lasts forever (despite the name of this website) and at least menswear timelines are long. Trends in womenswear are a lot less forgiving.
Interesting!
I am still into pocket squares. Often quite plain with a tie, like white, light blue or greyish in linen. But with more color when not wearing a tie.
But I have been wearing much more muted pocket squares the last 3-5 years. I love my Rubinacci silks but they are often “too much”. My “go to” pocket squares are now more often blends with linen or wool. Like the ones made by Christian Kimber.
I think that muted pocket squares adds interest to a sport coat withour being too much “in your face”.
And I still feel that a sport coat or suit jacket is a little bit “naked” without a pocket square. But a pin could be an interesting alternative.
I switched from purely decorative pocket squares to solid colored microfiber cleaning cloths a few years ago. The reasoning was that If I carry one for my glasses anyway, I might put it somewhere in reach. Are they as decorative as silk or cotton? No. Are they functional? Hell yeah.
As a guy who sells classic menswear for a living, I can tell you that the only customers I still see wearing pocket squares are either a) over the age of 60 or b) exceptionally bad dressers (think: fused blazer with a one-inch lapel, paisley pocket square, beige chinos, cheap, cognac-coloured lace ups). I can only speak for my hometown of Vienna of course, I‘m sure things are a bit different in other major cities.
In any case, that’s one of the reasons why I stay away from pocket squares and cuff links; they are meant to round off an already near-perfect outfit, but more often than not, they are worn by people who think that any cheap suit will do the trick, as long as you accessorize hard enough.
Just my two cents, keep up the good work.
Great two cents, thanks for the view from Vienna.
I think that speaks to the value of investing in good fundamentals in the wardrobe, doesn’t it? Those shoes would make such a better statement if they were better quality and well looked-after, and the handkerchief was left at home.
Surely there’s a similarity here with tie bars. They used to be all over the place (some parts of the internet still revere them) but some time ago I realised that they just aren’t worn by the people I would look to for advice on wearing a suit or jacket and tie.
Partly this might stem from not wanting to damage a very expensive and possibly bespoke tie with a clip, but given the way people like Simon wear ties, it just seems like something that would at best hide the tie under your jacket and at worst get in the way of the tie appearing natural – and it just won’t work with the sprezzatura way of wearing a tie.
I have white pocket squares in cotton and linen and if I’m wearing a suit I do like to wear them with a square fold – but I can never get the darn things to stay in position very long. I think a pocket square fits a suit very nicely, but depending on your milieu a pocket square on a tieless jacket might stand out in a bad way. Personally I can’t wear anything more than a dress shirt and trousers without everyone at work making comments about how well-dressed I am, so, I’m maybe a bit more constrained than most here are.
Sorry, I meant to put that comment under its own thread, not to reply to Andreas.
However, since I’m already here – I may have a pair of beige chinos and a blazer with rather skinny lapels and I might just have to get rid of them now.
Hello Simon, an interesting and timely article, as I was musing on this myself the other day. Inspired by your ‘How I store my clothes’ article, I did a bit of a wardrobe re-shuffle (not being allowed out of the house these days) and obviously, eventually, came to the handkerchiefs. (I’ve never called them pocket squares, for some reason?) Anyway, I did a large clean out of them as I rarely, if ever wear the bright silk ones anymore – except for 1 or 2 Rubinacci’s that are just colourful and fun – and find myself turning to the cotton bandanas and linens and wool/silk mixes; something muted, understated, and with texture. I will still almost always wear one, but stuff it with less material on display and with those less flamboyant colours and patterns.
Maybe I should keep the bright silks however for the next uptick in the cycle!
Cheers Nick, pleased you liked it. It feels like people are going that way, probably as part of the same feeling. Just less showy overall.
You might be waiting 10 years for the next up-tick, but then you’ll be laughing!
Hi Simon,
Great article. Can I ask what the fabric is on the blue jacket pictured with the white pocket square? I assume that its you in the picture?
Hey. Yes, good guess! It’s 9oz Zegna cashmere – taken from this post.
To be honest I wouldn’t recommend it, it hasn’t worn that well. Go for something with a little more body if cashmere.
Great, thanks Simon. I wasn’t actually looking for a cashmere but something with a bit of texture for a blue blazer I intend to wear casually. Its surprisingly difficult to find a blue wool with enough hand to make it casual without going to tweed. I’d be interested to know your opinion if you don’t mind me diverging to much from the theme of this post.
Yes I know what you mean, there aren’t many and there should be more. Wool, not cashmere but not tweed either, maybe in a herringbone or similar subtle texture. I can’t think of any off the top of my head, but I’ll let you know if I do.
@Anonymous: I also search something similar. Cashmere might be to delicate to wear often and tweed seams to be too casual. What about a wool/cashmere blend?
@Simon: I might be mistaken, but I think that you wrote somewhere that your Solito Cashmere-Jacket is the most useful jacket in your wardrobe? Is that not the case anymore if it’s to delicate? But as I said I might be mistaken. I think I asked this already, but wouldn’t a navy escorial be a nice option when Cashmere is considered to delicate?
Hey.
I’m not sure if I wrote that, sorry! I can certainly see why I’d say it: Navy is probably the most useful colour for a separate jacket, certainly if you’re in a remotely professional environment.
But I probably wasn’t referring to the weight of this cashmere. If it was heavier, perhaps from Harrison’s rather than Zegna, then it would be better.
Yes, Escorial would be a good option in that way.
I have a navy wool hopsack blazer from Isaia, and always appreciate the texture it provides.
I have never worn a pocket square to work (I am too junior and it would attract unnecessary attention, I think), however I try to wear one if I’m going out for dinner/cocktail/party/club. Thinking about it now, given that I work in an office of 1500+ people and there is only one guy I see around that wears one, I think most guys are similar to me. I also think that I will continue wearing one on these occasions in the future.
Also, on fashion cycles, if anything I feel like conservative clothing may be in for a comeback. Somehow, I feel that wearing £700 balenciaga trainers will be frowned upon when we get out of lockdown and are in recession. Much better stick to the collared shirt and blazer. This is to some extent based on evidence from aftermaths of previous recessions and the fact that conservative professions such as doctors (understandably) and politicians (perhaps more surprisingly) are experiencing high levels of trust, at least according to YouGov.
Best wishes, Simon!
Really interesting, thanks Nick.
I think you’re right on the conservative point – it’s not expense that’s usually the problem, but showing off expense. A bespoke tweed blazer, much worn and loved, does not show off expense. But a large gold watch or a designer brand name does.
Perhaps the same thing will also happen to the colour pallete of menswear. Something similiar happened after World War I. American menswear in the interbellum period was unusually colorful and flamboyant, most likely because USA didn’t really get hurt by the war all that much. In Poland clothing was much more subdued and conservative – wearing anything “fun” would be out of place, considering how fun the last years were. Though you could say it about any decade here 🙂 Either way, I wonder how will it impact style of brands such as Drake’s .
Really interesting, thanks Karol. We can be quite anglo-centric, really nice to get an alternative view.
Here’s a recipe for redundant pocket squares.Take one and lay it down flat in the shape of a diamond. Lay another beside it with a few inches of overlap in the same diamond configuration. Now roll them up together like you would a carpet.Place round the neck and knot like you would a neckerchief.The friction between the two handkerchiefs ensures that they will not fall apart.Handy,if your pocket squares are not big enough to use as a neck adornment by themselves.
Hi Simon,
Great to see the quality content continues unabated in these interesting times, and hope you are well!
On this topic, I comment I have is that while the trend has definitely fallen away, I would argue that menswear enthusiasts living in warm climates would still use pocket squares to add a little colour and flair where a tie would be too hot to wear consistently.
Personally, I’ve always found them a great way to add colour to a wardrobe of more traditional jackets (navy, greys), but especially for those with less extensive jacket choices than yourself!
A question if I may, with spring/summer upon the northern hemisphere, what are your thoughts on tailored shorts, especially bespoke? Is there a need for this, or is MTM/RTW a better option?
Cheers Ben, and nice to hear from you! I miss our days on Fleet Street.
Good point on handkerchiefs brightening more corporate colours of tailoring.
On shorts, two points.
First, you only need them bespoke to the extent that you will treat them and wear them as smartly as you would bespoke trousers. Which I think is rare for most people. And if you find you really need bespoke to get a good fit in trousers in the seat, hips and waist. I think you need both those things to justify it.
Second, most RTW shorts use different materials to tailoring and are garment washed (giving them the casual and faded look of chinos). This is something you can’t get with bespoke, as it’s a mass operation usually. So if you have bespoke shorts made, chances are they will look too smart, not like regular shorts. They could look just like the top half of bespoke trousers.
(It’s the same issue we’ve talked about before with the difficulty of getting bespoke ‘chinos’.)
I like to have all trousers made bespoke if I can, but I don’t have any bespoke shorts.
I would certainly recommend bespoke shorts as an option if you live on Bermuda, where they form an essential part of business dress.
I love my collection of patterned silk squares so much, but I’ve been thinking of moving away from wearing them for slightly different reasons than those articulated in your piece. I find that it just tends to become too much the focal point of an outfit – nearly everyone comments on it, regardless of whatever else I’m wearing. I think menswear aficionados view them as a nice finishing touch, but civilians zero in on them to the exclusion of all else (at least in my experience).
I’ve heard it said more than once that any one thing which completely dominates an outfit should be edited out. That conjures up images of loud ties or brightly colored hooped socks, but I’m afraid the humble pocket square might be also be in that category.
I hold the opposite view; I have only ever worn a pocket square as an occasional way of adding a splash of interest, rather than regularly. Thus, the frequency with which I wear them is unchanged.
Great Read Simon,
I am completely with you, I personally find myself wearing pocket squares less and less. It’s much more ‘showy’ than a tie and somehow seems more out of place in the corporate environment.
I also think a lack of square or just simplification of accessories in general just puts the wearer at ease, I’ve been particularly enjoying outfits from Jake at AIC for his relaxed elegance. Just appears less fussy, and if there’s anything that we don’t want it’s to look too fussy!
Also interesting how sprezzatura meant tonnes of accessories and drooping squares, and now this are changing once again
The graph is (kind of) interesting. I assume the main spike is Christmas but what are the other two? Father’s Day and??? Like you I still wear handkerchiefs but less frequently these days. Same goes for cufflinks, 3 piece suits and braces. I guess I am paring back all round. It will be interesting to see what happens fashion/ style wise in the coming recession and whether menswear will become more austere to reflect the times or more dandified as a reaction against it.
Actually the big spike is in May every year – I’m assuming during preparation for wedding season?
If not weddings, probably the Races.
I can see why people are wearing a ps less and less. It’s a hard look to pull off as it can make a man look old fashioned, like a dandy, or the worst, effeminate. So, at the very least, a ps should be simple, probably solid in color, and folded not just stuffed in the pocket. Probably the best example of wearing it right is the current James Bond, Daniel Craig. Personally I like having that jacket pocket open to hold glasses when needed.
Actually the big spike is in May every year – I’m assuming during the start of wedding season?
History would suggest the recession will make everyone more conservative, but then this isn’t a normal recession (very severe, but probably shorter lived)
Aah. That makes sense. thanks.
I enjoyed this post, and very much agree that “Clothing is a language and language is social.” You always have to be mindful about the setting in which you find yourself, and know how far you can deviate from that norm (e.g., by dressing slightly more casually or slightly more formally, using slightly different colors, etc.). That still leaves plenty of room for individual expression (and in a way, presents more of a challenge – finding a way to express yourself within a set of boundaries is more challenging and enjoyable than doing so in a world without rules or social conventions).
There’s a fine line between being elegant and looking like a dandy, and as an attorney, I’m always very careful to avoid crossing that line. I want to look professional and effortlessly elegant. I do not want to come across as someone who spends an inordinate amount of time thinking about clothes, for obvious reasons.
When I was a university student at Oxford, I used to go to dinner parties and formal events all the time, and I used to wear pocket squares all the time. Nowadays, I’m an attorney in Washington D.C., and I hardly ever wear a pocket square to work (at most, if I’m in suit and tie, I might have a tiny bit of white peeking out). Nor do I wear them for ordinary weekend events (again, trying too hard). I tend to reserve them for dinner dates with my wife, quarterly steak dinners with several close guy friends, and formal affairs.
My one point of disagreement is on pins, especially political pins. To me it comes across as a cheap form of expression. We live in a rancorous world in which everything is becoming politicized. I’m fortunate enough to have friends from a fairly broad array of perspectives. Those who know me know where I stand (or have a general idea) but I feel no need to advertise.
That’s very funny that a lawyer in Washington DC dislikes political pins.
Does he dislike Masonry, too?
In DC, you’re surrounded by political news 24/7. People either get addicted to it and become political junkies, or they get completely turned off by it. My job requires me to be aware of political developments that affect the industry sectors I work in but do not require me to be directly involved. Men’s fashion is one nice escape from it all.
The trouble with politics is that it becomes all consuming, and I know too many people whose happiness depends on outcomes that are outside their control, such as who wins the next election.
I very much like the idea of the pocket square having a functionality (in addition to being an element of style). I am therefore considering using home-made face-masks as pocket squares in the next few months…
Simon!
I second these opinions as I have myself moved away from anything showy. Funny enough, as soon as I could afford to buy quality, experimentation went out the window. I do have 3 lovely Rubinacci hanks, but as always with pure silk, they slip and slip and I find myself correting them all day long. Instead my plaincoloured and textured ones from say SG have been getting much more use, both in terms of versatility and stayin in place all day long. Like you say, for me to wear a hank these days, it needs to add something in terms of a colour combo that pleases the eye. Otherwise the tie does that when wearing a navy or grey suit. However, something tiny and made of metal can be a nice addition, even with formal wear.
Interesting that the quality point picks up on the comment above Nicolas – often showy accessories are an attempt (even a sub-conscious one) to cover up a lack of quality I think.
Simon, I have apparently awakened this morning as a curmudgeon. We are going to have to agree to disagree on this one. I guess I don’t care about being relevant. For me, the thing is to wear what you like, and not give a damn about what other people think. I wear what I like, including squares, and I don’t care if I look “period.” I don’t festoon myself with the square–it doesn’t look like a bird flying out of my pocket. If men stop wearing squares, who’s going to bring them back in fifteen years if no one ever sees them? Some kid going to prom? As for the pen, you are a brave man. I would never place ink anywhere near my jacket. It seems like a complete recipe for disaster. Pens in breast pockets are for scientists.
Good morning curmudgeon!
No seriously, all good points Rogey. The question of how much you should dress for yourself, and how much for society as a whole, is a big one and there isn’t space to go into it here. But safe to say it’s neither one extreme or the other. You can’t ignore society, otherwise you’d end up looking like you were wearing a costume. But you should express your personality as well.
On bringing squares back, it will be people dressing from a different period, and the look catching on again. As it was with Mad Men. People wanted to dress like the fifties in the noughties.
As to the pen, if it was a fountain pen then yes I’d be concerned. But not with a rollerball or pencil.
I have to agree with Rogey and Juan and join the group of curmudgeons, at only 47!
This post sent my mind rolling… into memories from old posts on this site, thoughts about the implications of the name of this site, and my own thoughts about pocket squares. On the one hand, I agree that with casual jackets without a tie, I’m less likely to wear pocket square, and as it appears to me that your personal dressing preferences seem to be following a more casual trend over the years, this post makes sense. For myself though, if I wear a tie, a pocket square is obligatory. And the main reason for this is because it’s my own personal version of style; my ‘permanent style.’ And like the other curmudgeons, I don’t really care what others think about how I dress, most of all the people that I simply walk past that look me over or only share a greeting with me at a party but don’t care about me any more than I care about them. For those that are closer to me in some social setting and I DO care about how they experience me, I make sure my manners and communication are on point and appropriate. I also have the benefit that my personal version of style (coat+tie+p.s.) isn’t inherently offensive and even if there’s a bit of show or something they think leans into a ‘period’ look, like my suspenders/braces, it can easily become a conversation starter or way to connect versus put someone off.
Also my mind went, aside from the above thoughts, was to phrases like…
“Michael Bastian, commenting on the growing trend, called the pocket square ‘the new tie’ way back in 2005”
– You had a whole post about this exact topic in 2008 (“The handkerchief as tie”) and this post seems to go a different direction. Not that I think you can’t change your views, just interesting to note given the contrast to this site name.
or…
“No clothing or style lasts forever (despite the name of this website) and at least menswear timelines are long”
-While I’m not too surprised at this post since you’ve mentioned wearing pocket squares less in other posts, I’m curious what you’re thoughts are regarding what ‘permanent style’ actually is and whether someone is expressing permanent style or a trend or fad?
I’ve enjoyed reading this site since it’s start and wonder – as your site has grown from a small blog that was a side interest, to quitting your day job and doing this full time where you’ve enetered the ranks of fashion journalists, I wonder if your own views of style and dress are being more influenced by the industry you’ve become immersed in versus a version of style that was or is uniquely yours?
Please know that while that was a little blunt, I have complete respect for you and have enjoyed everything you’ve created over the years and I’m sure this won’t change. I also realize everything I’m mentioning is more philosophical and perhaps going outside the topic of this post, so I apologize if it’s too out of place. Maybe a post on this type of reflective view about what ‘permanent style’ means to you in comparison to your outlook from years past would be worthwhile? Also, in a similar vein, I think a post about dressing for society versus dressing for yourself would be terrific.
Take care,
Tim
Hey Tim,
Thanks, all points absolutely taken in the spirit they were intended.
Specifically on the handkerchief replacing the tie, I still think that’s a good rationale, and it’s why I brought it up. I’m not stopping wearing pocket squares, I just wear them less, and one reason I would wear them is if I’m not wearing a tie, alongside other reasons like I feel like the outfit could do with more going on.
On dressing for yourself or others, I feel like a key differentiator with much of this discussion is how you work – with whom, and in what position. While society as a whole matters as well, it’s really the professional environment in which clothes can be particularly risky in the impression they give. I completely understand why someone that is retired, for example, might be able to care rather a lot less. And a young salesman saying everyone should just dress for themselves, is being naive.
On the site growing, I can understand why people think I might change to become more fashion mainstream, but I honestly don’t think that has happened. If anything, more people in the fashion industry wear pocket squares and dress up, without any regard to what ‘normal’ people might wear. I tend to be the one that is rejecting unrealistic fashion trends, whether it might silly waistbands on trousers, pyjamas as shirts, or sweaters tucked into trousers.
Last on ‘permanent style’ I think that is maybe worth a full post. Like all of these things, the answer is somewhere in the middle. Style obviously isn’t permanent, because we don’t wear frock coats anymore. But at the same time, we should push against fashions that last a couple of years, then die off. Personally I think wearing an accessory slightly less after 15 years (while everything else has remained pretty much the same) is almost as permanent as it gets.
Thanks again Tim, for the stimulating thoughts.
I agree with Rogey. In fact, I must be an old geezer as well… because I do not give a damn about what others think. Mind, I’m a litigation lawyer and never ever dress showy or the like… nor do I wear a frockcoat (that definitely would be period…). As the article rightly points out (nor that the rest is not right…lol) it’s never been a trend for me and I won’t drop it as such.
Keep up the good work, Simon.
The argument that you should dress only for yourself has always struck me as somewhat immature. After all manners, clothing, speech, gait, hairstyle, humor, all of these things are something like 95% propriety, 5% personal expression — depending on culture and character of course, some people being more eccentric than others.
Personally I’m not even sure the renewed interest in classic menswear over the past decade, which took place mostly online, will be enough to halt the general trend toward ever more casual clothing. Forgoing the pocket square seems to be part of that trend, just like wearing more separates rather than suits.
Personally I like the look of a subtle handkerchief, usually white, worn with a suit on special occasions.
Simon what is the jacket you’re wearing in the first image? I’ve just purchased something similar for summer and would love to see how you combine it with shirts and trousers.
It’s my Dalcuore – you can see more on it here.
Thanks Simon.
It certainly combines well with cream/beige trousers and a pale blue shirt.
Have you tired other combinations?
Yes it’s pretty versatile. Light to mid-greys work well, as does tan, and dark green
Yep. Been there, done that.
I’m not surprised that this trend has been dying out as I don’t think it ever really caught on in the first place. Most men who don’t have an interest in menswear tend to view anything superfluous and fussy with suspicion. Wearing something that you don’t need to and which doesn’t serve a practical purpose smacks of making an effort and making an effort in matters of dress tends to be viewed (quite wrongly) as rather effeminate.
You could tell guys just weren’t into it by the exceptionally small number times you were likely to see pocket squares being worn well ‘in the wild’. Nine times out of ten they were usually the wrong colour (matching a tie), the wrong material for the jack they were being worn with (silk with tweed) and / or worn in the wrong way (folded in a triangle like the end of the loo roll at your granny’s house.) It’s not a sight that any of us will missing seeing – regardless of your views on the humble pocket square.
The pocket handkerchief originated when gentlemen carried two fine plain white cotton/silk/linen ones. One in the breast pocket for “show” and one in the trouser pocket for “blow”. The breast pocket handkerchief could also be offered to a tearful damsel in distress or allow malady to blot a spill from her gown.
“Milady” not “malady”. I detest computers trying to second guess you.
Simon, the problem I have is that a lot of the “cultural norms” I see are frankly uninspiring and fairly awful. It’s genuinely difficult to find inspiration from others around me. Hopefully when we return post Covid people can just dress as they see fit and if it’s seen as “Period” or old fashioned so be it..Take care.
I was watching Paolo Sorrentino’s The Great Beauty last night and I noticed that the main character–who looked quite stylish even though his attire had many technical problems (weird shoes, large tie knots, smaller shirt collars)–was almost always wearing a pocket square. I never once thought this looked affected. Pocket squares often look very affected, but they didn’t in this case. I think there were several reasons for this.
-The main character of the city was in Rome. I think Rome’s architecture and ambiance may lend itself to bolder clothing choices (more than London, or New York might at least). I think there are certain places and certain times of year that are more or less suited to wearing a pocket square.
-It made sense within the character’s social milieu. A pocket square may not make a ton of sense in an office, but in social settings–especially more culturally vibrant social settings–a pocket square makes a lot of sense.
-The main character always looked very relaxed in his clothing. His clothing wasn’t overly pressed or overly tight. He was also older; I think this helps.
I guess the sartorial lesson here might be that pocket squares might make a lot more sense in some situations than in others. You shouldn’t just pay attention to whether a pocket square looks good with a given outfit. You should also pay attention to where you are, who you will be interacting with, what sort of activities you will be engaged in, etc. For instance, an outdoor summer wedding is a great opportunity to wear a pocket square. A sober business meeting isn’t.
PS: I also very much recommend the movie. There is much more to it than clothing.
I must say I own a few pocket squares but only ever wear them on odd occasions, for all the reasons you cite. I like the idea but the reality is often too contrived: Some guys wear them like soft furnishings. I might up my game now they’re less commonplace.
I’m reminded of a pal of mine at college who used to have similar weird squares popping out of his jackets. Turned out he was faking it by pulling the lining of the pocket up. Genius! Only a poor student!
Best wishes N
Simon,
Quite a thought provoking piece but one I can’t agree with. I’m of the same mind set as Rogey. In this day and age ties, leather shoes and even socks are being condemed to history. If this trend contiues will my grandchildren look at pictures of today’s “smart casual” man in raggety-arsed jeans, sloppy tee shirt with a mindless slogan on it, luminous coloured trainers with odd coloured laces and say “weren’t they elegantly dressed in those days” as we now say when looking at photos of classicaly dressed men at the turn of the century. God forbid !
I quarantine bought my first pocket squares last week. I never had any interest in them before now; but it looks like everybody is wearing them in the style websites. So am I adopting a dying fashion trend? Or am I the vanguard of the return?
I think you probably are adopting a dying trend Michael, yes. But that doesn’t mean you have to stop. You’ll just be a bit more unusual.
(On style websites – people on such sites, particularly brands, will often be more dressed up, combining more things than a normal well-dressed person would do. Mostly it’s because brands want to grab attention, and show more product. Even I have a tendency towards it sometimes though)
I wear my sportcoats “fully loaded”, so a discrete cotton or linen pocket square is essential as they often see heavy use. These days my pocket squares are doubling as temporary masks while out in public.
Why a button and not a lapel chain?
Cheers Troy. What do you mean by ‘fully loaded’?
I do wear lapel chains sometimes, but they feel like jewellery and for particular occasions, where a button does not. I also like the cause/passion aspect of a button.
Generally, I’ll have any combination of pen, journal, multi-tool, string, flashlight, lighter, USB drive, USD, or first aid supplies in my sport coats (with a pocket square to top it off). However, in addition to “normal” circumstances, I also wear them in more unusual situations like camping, trekking in the jungle, freighthopping etc.
Have you considered a bindle? I’ve heard they’re all the rage amongst the freight-hopping community.
Your brilliant banter provides the solution: (unwanted) pocket square + stick and Bingo! You’ve got yourself a snazzy little bindle.
I think menswear has been moving towards a more conservative palette in the past few years along with the move towards ever more casual tailored clothing. So it is not surprising that the pocket square has declined in popularity. However, for enthusiasts I would think that it would remain a regular item especially with the tie becoming less prominent. To me, there is very little room in a typical wardrobe where men can wear color and pattern.
Why did you pick 70 x70 cm PS scarves Simon? Why not any smaller or larger?
I found that was the perfect size (for this material) to be able to wrap neatly around the neck either once or twice.
It sounds quite big, but the material is so fine that it folds up pretty small.
Simon what MTO/RTW knitwear, shorts, outerwear brands would you recommend for smaller guys (say a 34″ chest)?
Scott Fraser has some models in smaller sizes, Colhays is too big — but do you know any more? Thanks~
Not off the top of my head, no. Sorry.
To follow the my previous question, I think Japanese/asian RTW/MTO brands are the way to go since they usually offer smaller sizes. Do you have any to add besides ‘craftsmanclothing’ Simon?
Good point.
I think particularly Japanese – less so Asian as a whole. Look for either Japanese brands or heritage brands (Barbour, Smedley, Mackintosh etc) that sell a lot in Japan. You may end up having to import things from Japan and pay for that, though.
Also, you could ask the advice of shops that are based in Asia, like The Armoury, Attire House, Brio and others.
Isn’t this another example of the difference between style and fashion ?
If pocket squares are your thing, they’ll be intrinsic to your look and will remain. The whims and fancies of ‘The Pitiful Pitti Peacocks’ won’t matter a jot to you.
Personally, I only ever wear a white silk square with evening attire.
For daywear, I’ve always considered them an affectation that distract from well cut tailoring but for some people they work. A lawyer friend of mine would look positively naked without one.
That said, I certainly won’t be putting a pen in my pocket or wearing a badge – that really would be trying too hard !
The battle between style and fashion has raged forever. Dougie Hayward and Tommy Nutter enjoyed their peak popularity at more or less the same time but as to which of them represented style remains in the eye of the beholder.
Hi Simon,
Excellent points. I think that a muted pocket square can indeed be ok for certain outfits if it doesn’t draw too much attention. I’ll have to keep my Rampley pocket squares for more formal ocassions.
How does the tie compare? Beyond formality, would the tie also be seen as a bit dandyish (outside of work mainly) ? Or is a tie in muted colours or even a knitted tie less affected by these trends?
I think the tie is seen more directly as something formal, perhaps corporate, even if it’s in a casual material or colour and pattern. It shouldn’t be that way, but it is.
Simon,
3 thoughts on your post:
– you are channeling Gianni Agnelli, who selectively used pocket squares. Conversely, his good friend, David Somerset, 11th Duke of Beaufort used squares with great flourish.
– many men do not know how to fold either a linen or silk square properly.
-finally, as a writer, I am a big wearer of scarves (channeling Lucian Freud), so a pocket square might be a bit much. Cheers.
Thanks Ned, as ever all good and interesting points. I do wish men would wear scarves more decoratively too.
Maybe an idea for a small feature (wearing/styling of scarves?). I know there is a post about strong colours in accessories, which focuses on scarves, but it is in a winter setting. Do you, for example, ever wear linen scarves in hotter weather? I have a few nice ones, but can’t quite get comfortable with them in an outfit
Nice idea.
We did do a video a while ago with Begg on tying scarves, which includes some lightweights.
But something more on styling with lighter ones would be a nice idea.
It depends on where you live. I’m in Hillbilly Tulsa Oklahoma! I truly believe I am the only man who wears one! Cary Grant always wore them. That’s enough for me!
Interesting view as always Simon!
Your analysis of the evolution of trends is spot on as far as I can gather.
From a more personal perspective, I simply love my pocket squares, whether they are printed silk or linen/cotton ones. I have to admit that I feel naked without wearing one and that I still prefer to wear a pocket square instead of a tie if I have to choose.
I never watched Mad Men but am happy to find out that my own discovery of the pocket square squares (yes, pun) with the series, as it was in 2007–back then it seemed outrageous to a young 27 year old me to wear one, but I overcame my initial scepticism and have never looked back.
Long live the pocket square and long live the freedom to dress however one chooses to–what great times we are currently in, mixing-and-matching everything!
Best, Laurent
Cheers Laurent – a nice example of how to disagree elegantly, i.e. without sounding like a ranting curmudgeon!
Oooh… good one! Ahahaha!
Simon – great comment. Would you mind saying where your red blazer is from please?
The pink cord jacket is from Orazio Luciano – see the review of it last week, here.
Finally someone wrote it. Well done Simon. I stopped wearing them (with some exceptions) a few years ago because of the ubiquity you mention. Now, it seems to be an everyday accessory for those who dress a bit too costumy for my taste, or the Pitti Peacocks, or the showy salesmen.
I’ll stick with my hankies, now even more so, its my tiny, hopefully elegant, surely futile, rebellion against ‘the man’ and acres of grey worsted conformity.
I pick them sometimes to balance and sometimes to complement. If I have lots of colour and patterns elsewhere than maybe a calmer one. If its a grey/blue suit sometimes to add a dash of colour but when its a meeting with the grown ups sober and white.
Dear Simon, interesting article as always, thank you. I am bit disappointed you are this sensitive to trends though! A pen in the breast pocket? A button on the lapel? A tattoo on the arm? Not for me, thanks. I don’t like empty breast pockets and I can’t think of a better thing to fill them with than a nice (small) bit of cloth that echos the other pieces of the outfit. I am secretly a bit excited about the handkerchiefs going out of vogue – we can keep wearing them without looking like we are following some silly trend
You’re right, that’s certainly an advantage.
I’m not sure about the point on trends though. It’s a small shift from a piece of clothing being a default to being an option, after a decade of it being the former.
Also, the other points are rather contradictory. You think I’m following a trend in getting a tattoo (even though that was the one thing that put me off), and also by wearing a button or a pen in the pocket – even though no one is doing those last things? You can’t have it both ways!
Good point! It is a bit contradictory. I guess replacing the handkerchief with other items such as pens or buttons comes across as a little bit gimmicky – sensing that the pocket square is becoming a bit too mainstream and replacing it with something unusual is perhaps not following a trend but participating in one? I guess the tattoo fits into this story because it is also a bit of a rebellious move! It used to be anyway. Keep up the good work please.
Seems like impermanent style.
I wear a pocket square. Linen or cotton if I have a tie on for business meetings (probably 1-2 times per week on average when not in lock-down). Patterned silk if I don’t have a tie. Even though my office has converted to American business casual (basically no rules), as the attorney in the executive office, I feel a need to wear a jacket even if I don’t have meetings with anyone external. And, whenever I wear a jacket, I wear a pocket square. On Fridays, if I don’t have meetings I wear a sweater or casual pattern button down collar shirt without a jacket and cotton trousers. Obviously, no place for a square with that outfit.
I just can’t figure out why jackets have pockets there if not for holding a square.
There are lots of things they have that are useless Eugene. A buttonhole in the lapel, for instance. Buttons on the cuffs. I think whether it ‘looks’ empty is mostly just a question of how often you are used to seeing it filled.
1 phone on each side pocket and glasses on the breast. That pocket isn’t for a handkerchief really, sartorialist just want to find a way to add more things to their outfit. As wfh we dress down many suits and jackets, those things aren’t trendy anymore.
A gentleman should have three handkerchiefs with him at all times. One for show, one for blow, and one for when the ladies glow.
Hi Simon, these questions are important to ask and I guess now is a great time to be musing about the philosophical theories surrounding different items – particularly accessories. I nearly always wear a pocket square with a jacket. I have a broad (inelegant) chest and I like to break it up rather than present a huge expanse of flannel/tweed/corduroy/etc. That isn’t to say that my choices have remained constant, I rarely now wear exuberant brightly coloured silks from Charvet, T&A and Hermes, but rely more on wool, linen, cotton, cashmere squares in white and muted tones of cream, grey, beige, taupe, khaki and blue/grey. These squares will be just as easy to put in my trouser pocket should my opinion change in the future.
Accommodating trends should not result in one becoming less of a gentleman and a gentleman’s breast pocket is never empty. The breast pocket on a suit jacket was originally designed to hold your nose wiping cloth so that it was not commingled with the dirty items you’d be carrying in your jacket’s regular pockets. A gentleman would never hand a dirty handkerchief to a lady, so in modern times the practice became: the one in your pants pocket is for you and your nose, the one in your breast pocket is for her. Obviously, you could carry the handkerchief for her in another pocket, but since almost any alternative you’d be carrying in your breast pocket – like a pen – will eventually destroy the jacket’s material by sliding in and out, why not simply be a gentleman and use your breast pocket as it was intended to be used. If you still feel compelled to bend to trends, you can vary the material of your handkerchief, carry a pocket square, vary your fold, etc. Be a gentleman!
Having been and continue to be an avid wearer of the pocket square both in business and pleasure .I am interested in your thoughts on the rather recent trend of showing the Edge of the square .Personally I prefer not to as I feel it draws attention to item and away from the look
Hi Henry,
I’m not sure how recent that is, but you’re right it’s certainly widespread. Most folds, whether a simple square fold or one with the points coming out of the pocket, show the edge of the square. Interesting that you think that is too showy. I guess it’s less so in a simple white linen, but more in a silk with perhaps a coloured border.
I think some also like showing the edge out of the pocket square because it reveals the hand-rolled craft of those edges.
Pocket squares from makers such as Brioni and Stefano Ricci now cost in excess of $150. Do you think these brands killed the goose that lays the golden eggs ?
I’m not sure price put people off to be honest. People buying from those brands don’t pay much attention to price, and there are lots available at much cheaper prices without sacrificing quality.
Hello Simon,
Great article; always read, but rarely comment.
Back around 2010, I went through a period of experimenting with pocket squares; in suits, sports coats, even overcoats. Finally came to a style I favor – called a “TV fold” here in the States – very subtle, and only use this now when in suits, and to dress up a blazer on occasion.
Someone once said of Cary Grant that they always thought he was well dressed, but could never remember just what he was wearing. An admirable standard to which I aspire.
Being a bit older (early 60’s), I feel like I’m straddling a line between trying not to look too old and staid, and trying not to look foolish in appearing as though I’m trying to dress “younger.” I’m comfortable now with my personal style and approach; it has more to do with proper fit and what compliments my physique, than fashion trends.
Hi David, thanks for the comment.
An admirable aim indeed, and the folded square works very well in that aim of subtlety. It’s interesting how many readers still like the pocket square, but are just wearing them in more understated ways, like you.
As someone who has never required the formality of a tie in daily life, I’ve toyed around with pocket squares in order to punch up my outfits but never felt right and eventually gave up on them. I think in the end it’s because, like ties, they simply do not perform any function, despite my telling myself they could be used in countless useful or chivalric ways. And that’s just how it goes—we lose traditional bits of menswear because they lose their usefulness, even if that use is only to peacock a bit.
Perhaps a statement of the obvious but the geometrically folded white pocket square is different in every way from a puffy patterned job.
Adding contrast properly ups formality and austerity. See Charles Dance as Mountbatten in the Crown. Individuality is overrated.
Simon – So what are we do with our drawers full of pocket squares? Reconfigure them into face-masks? They weren’t cheap.
If you have more than one drawer you might be in trouble! But as with me, I think they’ll still be worn, just not all the time. I probably only wear a tie one or two days a week, but I still have a fair few.
Also, give them away or sell them through one of the many second-hand online shops. Many don’t have so many.
Pencils and pens, why not.
Lapel buttons, just makes me think of the Young Ones, not in a good way
But then if you feel the need to do things to compensate for the lack of a pocket square, maybe you should just wear a pocket square.
I do not think I am going to give them up. I like them and that is enough. If the mainstream wears them less it makes no difference to whoever wears them out of individuality.
I also think wearing them is a sign of sophistication, since it is more difficult to add them to good effect (lots of examples here on how they can be worn wrong) than to forego them. And I believe the walk through life should head to sophistication.
If anything, less people wearing them just means an increased challenge to wearing them well. Not a challenge I mean to miss.
Very interesting. I think for those who work in the City (London’s financial areas), the pocket square would generally be seen a somewhat eccentric. There is a great deal of uniformity there in terms of dress (dark suit, black shoes, plain white or blue shirt), which may be the factor. I’ve never been keen on pocket squares outside of black tie – I’ve always felt they were a bit too showy, when my personal goal was to look smart, with well cut suits, but never stand out, or worse, look like I was into “fashion”.
“Clothing is a language and language is social.”
Particularly pertinent given how mute many a sartorially inclined have been feeling as of late.
I have personally come to admire the ‘pocket square’, especially the highly motif-ed style by Rubinacci, Eton, and Rampley et. al.
I always wear a tie by choice. So that said, when I wear a suit I use a clean crisp tv fold white pocket square to break up the form. With a odd jacket, pants of a different color, and tie of a third color, I find any pocket square to be too much. Often an overload of too many colors and patterns and just feels off to my eye. I can see a square being an acceptable tie replacement though.
I also find myself regularly putting the square on and then taking it out, but I wouldn’t think of putting something else in that pocket.
Two weeks ago I saw someone in the supermarket using that pocket to carry his cellphone, and I see no difference between that and the pen.
I’ve tried that with my phone – one difference is the phone falls out very easily! Very annoying
I know others who use a phone too. Oddly enough just the right amount of the tip of the phone shows to almost act like a ps
That’s great, find some paisley wallpaper for the screen and there you go.
BR
Just (over) thinking about it… I wonder if we would be discussing this issue some 50 years ago, when no one stopped to think twice about wearing a pocket square… It was a trend? Don’t think so. It was something one just wore? Maybe.
This topic must be the longest I’ve ever seen here on PS…!
I let the occasion influence me to choose a square. Of late, I’ve taken to a surgical mask as the square- when not required worn by guidelines. I also hope this “square” serves as a gesture towards solidarity in health matters. Best.
Never thought of pocket squares as a trend. My grand father used them and so did my father when wearing suits.
It’s the natural thing to do.
As someone once said ” there’s a pocket there—stuff it.”
Gentlemen,what’s the point playing the game called classical menswear style if abandoning one of its most beautiful anchors The Pocket Square..”
M
Hi Simon,
I saw ads for Rampley & Co on Instagram, what is your opinion on this brand?
Thanks.
The only thing I’ve tried is the pocket squares, which I didn’t like that much because they were digitally printed. That’s necessary with a complex design like the oil paintings they used, but it does make the colours a little less rich, compared to dye and discharge
This article really struck me reading it last night. (I’m a bit behind on my reading here – I used to read you at each update, but ‘looked away’ for a while during this pandemic, and now I’m relishing catching up).
‘If you want to appear in any way relevant – and not ‘period’ – you need some awareness of cultural norms.
Clothing is a language and language is social.’
There’s wisdom in these words Simon.
But frankly I was caught by surprise that the pocket square is on its way ‘out’. And that brings us to fashion v style, something you have helped us all understand (and hence part of the surprise in this post). You have, to be fair, pointed out numerous times that style is not in fact ‘permanent’, but style shifts more slowly than fashion, especially in today’s cycles. (You illustrate this point again with tailor’s lapels v the fashion widths). But, having taken an interest in ‘style’ in what your graph neatly points out was the high point of the pocket square I had somehow equated it with something more enduring, especially as when you read some of the key texts on men’s style, the pocket square is there across many reference eras. It seemed to me, in other words, somewhat timeless. Or, lets just say I thought this thing was moving slower than perhaps it is.
As I was reflecting on all this I was thinking about some of the early posts you have on this website, written just as you were getting into serious tailoring – around 2008 (?). Sometimes in later articles you point out some of your mistakes, or some things you might do differently if you were to repeat the exercise. Those usually focus on things like fabric or cut, or some detail. And sometimes you follow that with a comment that as a result you don’t get much wear from that piece anymore. What I hadn’t considered (and I don’t think you have addressed this in your writing – but if you have please point me to it), is that you might not wear some of those earlier pieces now because of changes in *style*.
So here is my question, and if not yet addressed, perhaps there is an article in it (?) – if you look at those pieces you commissioned back around say 2008-2012, what proportion of them are you now not wearing for reasons of *style* (rather than aesthetic or functional ‘mistakes’ on yours or the tailor’s part)? What still looks good and wears well, but you don’t wear it because its too dated now?
(And, coming back to your ‘relevant’ v ‘period’ point, this could be expanded to encompass not only looking ‘period’, but also fixing a distinct look for oneself, which is not period per se, but isn’t relevant either, it’s more eccentric – e.g. Boyer, Jacomet, etc – great dressers, but not ‘relevant, if I take your meaning right).
Meanwhile I’m off to find or make a lapel button that reads ‘I miss the hank’. 😉
Nice idea Linden, yes I’ll think about that. I think there will certainly be some of those earlier outfits that are less relevant, but I’m not sure the clothes themselves were, more just the way they were worn sometimes.
And good plan on the pin. I also suggest ‘Bow ties are cool’ (Dr Who)
Hi Simon, Just re-reading this article after a long time. You know, I am really interested to hear you revisit the concept of “permanent style” head on. In this article the pocket square comes under fire mainly because it has been declining in its fashionability. And while that might be the case – you provided some empirical evidence of that – many in the classic menswear world continue to wear such things as high-rise trousers , pleated trousers, A-1 flight jackets as mainstays of their wardrobes. These are arguably are much worse offenses in regards to fashionability as these sorts of things or not merely declining in fashionability, they haven’t anytime recently been considered fashionable, in the first place. The justification for wearing them is usually that they are examples of “permanent style “. If that is correct, then why any justification to reduce the frequency with which you wear a pocket square whose status In regards to fashionability is far better than any of these other examples?
Thanks Ajay, interesting question.
There is really no such thing as permanent style. Merely longer lasting style. By focusing on classic dressing and elegance, we wear clothes that look good and relevant for a decade or two, rather than a year or two.
Because none of it is permanent (we’re not wearing frock coats anymore, after all) some changes like wearing a pocket square less will always happen. But it is important to distinguish between the two types of ‘fashionability’ – changing something after 20 years is very different to changing it after 6 months.
I hope that makes sense.
Up the Irons Simon!
Hi Simon,
Would you say there’s a difference in formality between cotton and linen pocket squares? My instinct is to say linen is more formal because it’s a stiffer material. Similarly, would you say a pocket square with a drawn thread edge is less formal than a hand rolled edge?
Essentially I’m looking for a pocket square that will be most useful in a business (law firm) and smart evening context, but can’t decide between the following three.
https://shop.anderson-sheppard.co.uk/drawn-thread-linen-pocket-square-white
https://www.drakes.com/accessories/formal-accessories/box-of-three-classic-white-irish-linen-pocket-squares
https://www.buddshirts.co.uk/plain-batiste-cotton-handkerchief-in-white.html
Happy to be pointed in the direction of other makers you think might be more appropriate.
Many thanks!
Linen is more formal than cotton, and hand-rolled edges a little more formal too. But they are small points. Of those I’d go for the Drake’s
Can you use the same pocket square every day? And do you have to wash pocket squares every now and then?
If it’s white, yes you can. If not, then no, it’s more like a tie and should be changed.
With white linen or cotton, yes you will have to wash it every now and again, just because it’ll get a little dirty with handling
I think that pocket squares are nice for other people but I have never considered them nor would.
Moreover, boutonnieres are tacky and the only person who can pull it off is Tom Wolfe.
Simon, please, what are standard depths of the breast pocket for English and Italian bespoke suits? And what depth do you think is the ideal for solely pocket squares use and for multipurpose use (pen, spectacles etc.). Thanks! John
Hi Simon, would you wear a linen pocket square with knitted polo under a sports jacket?
Many thanks,
Jack
Yes
Simon, I certainly understand why you said you would still continue to wear a pocket square with a proper suit and tie, but do you feel like the recommendation of using a pen works with a smart suit, or just our jackets?
Probably just jackets, or at least more.
Hi Simon.
I have a question regarding the pen/pencil from Yard-O-Led you are wearing in your pocket.
Is it a pen or a pencil?
If its a pen, aren’t you afraid that i will leak?
Best regards,
Christian.
It’s a pen, but a ballpoint, which don’t really leak. I would worry if it was a fountain pen, yes
Hi Simon, would you suggest wearing a white linen pocket square for a formal event such as a wedding? Or are there any other colours or materials which may work?
Many thanks,
Jack
Others can be nice, particularly if the shirt and tie are simple. But I would default to a white linen, yes
The pocket square will replace the tie. Look at the recent photo of the G-20 meeting. No one is wearing a tie.
I’m not sure about that, unfortunately. I think the pocket square is too unusual compared to the tie, for most people in most work places at least