Wear loafers with jeans

Monday, October 10th 2022
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In the hyper-casual world we’re living in, any opportunity to add a little smartness to everyday clothing should be grabbed with both hands. One of the most effective ways to do this, I’m finding, is wearing loafers with jeans. 

Jeans are what most men will put on as their default at the weekend, and many during the working week as well. It’s then easy to follow them with the obvious partners: a T-shirt and a pair of trainers. 

But a casual loafer, such as the Alden cordovan tassel loafers pictured here, immediately make things both smarter and more interesting.  

Of course, it can’t just be any loafer. It has to sit some way down the casual scale, as we discussed at length with regard to trousers here

Suede or a more casual leather like cordovan are the most obvious materials. And often in a more casual style too: not a slim, thin-welted Cleverley, but a chunkier, round-toed Alden. 

My particular favourites are the two pairs from Alden pictured here: a brown cordovan tassel, and a Color 8 cordovan full strap. They’re both on the slightly slimmer Aberdeen last, but the Alden make up is rugged enough, and I still wear my jeans slimmer than some. The regular Barrie last would fit with a wider range of jeans (and chinos). 

This look has a few different effects that I like. 

One is that it adds personality to what can otherwise be a fairly ordinary look - T-shirt, jeans, trainers - without adding bright colours or fashion-driven sneakers. It’s still subtle.

A second is that it stops an older guy looking too young. There’s something about that tee/jean/trainer default that can be a little infantilising. 

And a third is that it stops men looking simply sloppy. Of course there are other ways to avoid this, including wearing neater, cleaner versions of each piece, but substituting a loafer for a trainer is probably the easiest. 

To me, there is something of the Ivy spirit in a combination like this. 

To many Ivy purists, jeans are anathema; to others, a shirt will always be better than a T-shirt. But the playful combination of smart and casual, using easy, practical pieces, seems in keeping with what I take from the original Ivy mentality.

The jeans can be thrown on, and look better the more they’re worn in. The same with a cordovan loafer - quickly slipped on, and tough enough for the park, the rain and the grass, as long as they’re given a wipe down and a brisk buff afterwards. 

Why a loafer rather than a boot, by the way? I think just that a boot is more common, less unexpected, and most of the time more casual than a loafer too. 

One brand that does this look well is Horatio (above), which makes (to PS) mid-market loafers in Italy and in the Far East.

The marketing is very effective at showing a guy who mostly wears trainers, how good a pair of shoes can look - whether it’s a penny or a snaffle, with black jeans or blue. 

Of course it’s also something someone well-dressed like Ethan (below, far left) has been doing forever. But hey, I was always a late adopter. 

At the weekend when I get up and go our - often a little too early, to take a bouncing three-year-old to the park - I instinctively pull on a T-shirt and jeans. 

I might wear a Cashmere Rugby over the top, often a vintage piece like an M65 or a jungle jacket as well. But it’s the choice to wear smarter shoes rather than trainers that makes me feel most like I’m wearing something interesting, something personal. 

In the pictures here, that T-shirt is a PS Tapered Tee, the loafers are a Trunk collaboration with Alden and the jeans are 80s Levi’s (though let’s the argument about rips for another day - a fight like that deserves its own space). 

The blouson is not an especially good illustration of today’s point, as there’s certainly nothing boring about it. But it is perhaps a good illustration of the point made a couple of months ago - that there’s some good vintage shopping to be had in Florence

It’s a seventies suede popover from Hermès, which I bought at Desii this past summer. Suede is not the easiest thing to buy vintage, but it’s clearly been looked after well - there is a slight darkening here and there on the surface, but otherwise it’s unmarked.

Being a popover, it is quite voluminous in the body, especially the waist (see profile image below). 

But as we discussed with casual outfits at Pitti, or is the case with the alpaca cardigan I featured from Anatomica, as long as the body isn’t too long, a roomier fit can be fairly flattering. 

The jacket cost €700, which is certainly not cheap. But a new piece from Hermès today costs thousands, and of course the advantage of a vintage one is that you’ll never see anyone else wearing it. 

I wish Hermès did more pieces like this - more playful in a colourful, Arnys manner, rather than the H stripes and robot prints they define as playful today. Perhaps there’s room there for someone like New & Lingwood to take up that mantle. 

Photography: Milad Abedi

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Peter Hall

You really must offer your Oxford as a popover. That Hermes one looks great.
I have a pair of chunky-soled black weejuns for exactly this . They are great with jeans and a striped Oxford.
If you discuss ripped jeans…Friday afternoon and step away from the computer.

Peter Hall

I think a white popover is a nice addition to a summer wardrobe and goes well with the Ivy sportswear style- although you will lose the slim fit of the PSshirts. I just love the collar on the PS oxfords.


Linen and chambray popovers are my go-to during the summer months – I find they work particularly well with shorts. If you do decide to do a popover using the Oxford collar, a stripe might be more versatile?

Peter Hall

I thought white as a top layer in summer and a base layer under a knit for winter. But,a stripe would be nice.It’totally subjective,for me-I have plenty of striped Oxford.


big fan of all shirts pop-over here


Would be nice if you could do a review of the horatio loafers while you’re at it simon (or this was what i expected when you were talking about horatio in the article)


I would also be interested but also weejuns would be a very good idea to review since they are the loafers that made me start my loafers-journey. Of course not the quality of alden but if someone has 250 euro to spend a lot better than some trainers. On the cheaper loafers i never use trees and i really dont care to do so so they stay always ready to be worn everywhere (like the common projects pair you used like that). Would the crocket jones shell cordovan loafers fit the style too or are they a bit more formal ? Could you post the link of the alden shoes on the photos ?


Are they the cigar cordovan ones? If so, that’s my favorite cordovan color and on an Alden tassel it’s perfection. If they were on the Copley last, I wouldve purchased right away. Enjoy in good health.

Aaron L

A ‘stay away’ judgement can also be pretty helpful. The mid-market space is a real minefield. It’s hard to know what you’re sacrificing…

Evatt Gibson

I’d certainly be interested in a review of Horatio’s. Their loafers have a somewhat different look from Alden’s and they have been enthusiastically endorsed elsewhere (e.g. Jake Whigham).


I would be very interested in a review and interview with the Horatio boys. They’ll have a great story to tell with a history going back to the original Duffer of St.George shop, Timothy Everest, and the Present shop in Shoreditch. Some great London institutions. Subverting high end brands and mixing them up with vintage and casual gear since the 80s. Get Tony on the case!
The shoes are well made and great value.


The shirt looks nice, but can it even be washed or dry cleaned?


Not the right post for it maybe but just wanted to say how happy I’ve been with my PS Tapered T-shirts since you mention them in the article, Simon. Very robust cloth, flattering fit. So much so that I hardly ever reach for my Warehouse ones anymore. It would be great to see a grey-coloured version sometime soon. 🙂


Another thumbs up from me – I’ve had numerous compliments on mine


Hi, totally agree on loafers with jeans, however prefer a little chunkier and definitely penny loafer. In my case wine colour Bass Weejuns (repaired countless time!) and tan nubuck but not for wet weather. I do struggle with no socks (one for another column!) though only because of comfort, so tend to go with a tonal pair. Also a couple of old beaten up Sebago dockside’s nicely salt marked – but not really for in town – which I have had for many years and for me are a worthy of ‘how great things age’.
I’d say this look is definitely an authentic interpretation of Ivy.
You can probably tell you’ve hit on a long standing personal favourite on mine!

Leigh LS

You can buy true “no show” loafer liners. They certainly don’t offer any support, but they’re cut specifically for various loafer shapes, if you’re just trying to avoid rubbing or bare feet.


Btw sorry forgot to add I think the whole look Ethan has put together in the photo is great. I just never seem to quite pull it off myself!


Simon, what kind of sole do you favour on these loafers? I ask because while leather has a certain ‘something’, it wears through really quickly if one wears the loafer a lot / casually. But then rubber soles have a certain ‘stodginess’ if you will..(!)


Although not exactly the topic covered in this article, PS readers, what would be brand recommandations on mid washed jeans, mid high rise, tapered leg (not too slim) ?


P.A. Drakes or Anglo-Italian’s house styles are exactly as you describe.
I recently bought a pair from Drakes and like them.


Thanks David, although I really like the Anglo-Italian ones, these are completely out of budget for me.
I can’t justify paying 250€+ for denim, it will get beaten up, stained, and I don’t care that much about it being selvedge or not.


You could try some Levi’s 501s. Way cheaper than Drakes or Anglo (obviously won’t be as nice, but they’ll do the trick).


Something I really ought to do more. I’d love to get an Alden LHS. I tried looking for slightly more budget ones, but none of them come close enough I think. Will check out Horatio later for sure.
Would you consider these loafers to be too smart to go with jeans?


They look very much like Loake Whitehalls. I have that exact same pair and don’t really like how they look with jeans.


Hi Simon,
Beautiful styling, as always. Your eye for colour combinations really is great. Also agreeing on the harmony between loafers and jeans – perhaps best championed by stylish Japanese men (as illustrated by the Ametora cover) and the L’Etiquette team. And especially effective in casual offices.
As a fellow dad, however, I find cordovan leather soled loafers deviate too far from standard dress in the park, and especially so with tassels. First, because cordovan is so shiny that people easily remark ”oh, you are wearing dress/patent leather shoes”, being prominent just as a conspicuous trainer would.
Secondly, because of them being ineffective for the occasion: going to the park involves impromptu running, climbing, loafing around in sand, mud and other activities which require more traction and flexible shoes that stick to your feet. I prefer paraboot-style derbies or Rancourt-style mocs instead. Perhaps a rubber-soled chromexcel penny loafer would work.
It might also be that my neighborhood is less conservatively dressed than yours (appropriateness being relative etc). Nobody wears oxford shoes nor dress shirts in the park, instead people lean into gorp-core, workwear and similar styles. Lots of pile fleece, chore coats and blundstones.


Thanks Simon,
I guess I will have to take my Aldens to the park and try! And thank you for the tip. I try to aim for a sheen rather than a shine, if that makes sense.


Hi Simon, what do you usually use to wipe the cordovan?
I have noticed there are some water spots. They disappear once I put cordovan cream on, but it would be good if I could remove them after every use.

Many thanks,

Matthew V

Loafers and jeans have been a default combination for me, on and off, for many years. With a smart blazer and shirt back in the day although that did look a little too “rich European playboy” at times!

Matthew V

Yes it is all about the fit! And lets not mention bootleg jeans circa 2000, way too Jeremy Clarkson in hindsight (yes I was guilty of this).
A PS Friday polo, battered jeans and loafers feels a nice combination.


loafers with jeans is a great look that I employ often, and imo alessandro squarzi is the OG of this fullstrap + jeans look.
where did you find the jeans and what model are they?


What watch is that with your t-shirt and jeans?


Hi Simon! It would be great if you could help with a couple of questions.
1) I had recently purchased a couple of popover shirts in view of it being a good replacement to normal t shirts. What is it specifically that you do find fussy about it and whether than should somebody opt for a normal Oxford shirt rather than going for a popover?
2) Would dark brown suede derby shoes look good dark denim?


T shirts i have found is one thing I am not particularly comfortable in because my arms are not that built and therefore I try looking for alternatives to tshirt just to respect the social propriety as you have always suggested. Now I have realised that regular casual shirts like Oxford or chambray if dressed with sneakers and jeans would not be huge step away.
Thank you for your advice.


Would your dark brown suede derby look good with mid blue jeans?


“In the hyper-casual world we’re living in, any opportunity to add a little smartness to everyday clothing should be grabbed with both hands. One of the most effective ways to do this, I’m finding, is wearing loafers with jeans.” Or not wear denim which is the epitome of hyper-casual?
To many Ivy purists, jeans are anathema; to others, a shirt will always be better than a T-shirt.” Many stylish men, not just “Ivy purists”, would agree. It’s just as easy and smarter to wear well-cut trousers/chinos and a collared shirt, e.g. a OCBD or Sea Island polo.
I’m fed up seeing the boring and bland, “uniform” of Dad’s jeans, t-shirts, overshirts/chore jackets, sneakers and even baseball caps. To fight it, I try to set an example by wearing smart alternatives at all times. I thought that Permanent Style shared that view but it seems that, sadly, I was mistaken.


Hey Simon,

Do you think a similar effect can be achieved with derbies? Perhaps of the more casual chunkier variety?



I personnaly love the raw denim and chunky derbies look, especially the kind of Weston demi-chasse.


You don’t mention your Alden LHS for wearing with jeans. Any particular reason? I’d have thought they’d have been perfect for that purpose?


How about the LHS in cordovan? If the suede version is great as a casual option in the summer, wouldn’t the LHS in cordovan look great and just as relaxed with jeans, but a notch above trainers?


Sand = milkshake or tan?
Or did Alden used to have sand color as well?


Love this piece Simon. I’m just not a trainers guy, but that doesn’t meant that I want to look like an elderly history teacher either (I’m only in my 40s). It’s a hard balance and I find loafers a much safer bet than shoes.
On a similar note, I love the Ivy look and the modish style it gave rise to. I recently bought a Baracuda harrington, and my wife isn’t a fan. She thinks I’ve strayed into costume and I look like I’m trying to hard to force a “look”. I get what she means, but in my head it’s a slight extension of other items I’ve enjoyed for years, like trickers boots, selvedge jeans*, Oxford Button Downs etc.
Any ideas? What is too far, and does it even exist (answers on a postcard).
*(yes, I know that some mods hate jeans)


you may well be right. Much as I like the ivy / mod look and style, I’m not a mod (and I suppose few are). I’ll mix it up more

Peter Hall

Swap the Harington for a parka.
Small steps before you get the vespa ,Charles.


I am not convinced.
Jeans signify a rough/sporty/cool look. As such, I think, they work well with sneakers, chukka suede boots and rough derbys with a Vibram winter sole (see the winter edition of Crockett and Jones in rough out suede).
By contrast, loafers are fine, light and somewhat feminine shoes that, in my opinion, work only well with dress-trousers and rather fine chinos.
Further, I find that loafers are typical summer / late-spring shoes but jeans really are late-autumn winter pants.


Sorry Simon, I did not want to sound that absolute and I see your points on wearing loafers with jeans, just not for me.
As to the winter issue, I have a more “objective” opinion considering my background and I guess the reason is twofold: (i) Our winters are very different from English ones, snow, snow slush, salt and gravel (or ice) on the streets on most days, often needing somewhat higher shoes that snow does not come in from the top, etc. This makes loafers – and anything with a smooth sole (slippery surface) – quite impractical on most days. (ii) Probably due to that background, nearly nobody wears loafers in Austria (and as far as I am aware also in southern Germany or Switzerland) in the winter, these being considered (Italian style) summer shoes. So you would likely stand out with loafers in winter, likely not in a good way because a lot of people would think you misdressed (like wearing only a light cotton sweater when it has 0 degress). But this, of course, only applies here.


Oddly enough, when ice enters the equation loafers work surprisingly well. My absolute best pair of “walking across ice” shoes (outside of my hockey skates) are a cheap pair of boat shoes! Several of my loafers work almost as well. Quite ironic that my snow boots are horrible on ice but my dress shoes grip like a gecko.

I’m good with dressier shoes worn with denim IF the denim isn’t too… ahem… well-loved. If they’re worn and faded, suede is the way to go. Otherwise, I’ve worn cognac captoe Oxfords with (my one pair of) jeans to good effect before. A proper pair of shoes can make denim look fantastic, but no pair of pants will dress up trainers.


I disagree. Your comment may be true for some loafers. But when you look at Alden cordovan loafers, they are really chunky and not feminine at all and cordovan as a material screams „autumn“ for me. Therefore such loafers are the perfect match for denim to my liking. (Btw: in my opinion Alden prices, especially for cordovan have gotten way too high recently. I myself would not pay Edward Green prices for their shoes. So I am glad, I already have two versatile pairs from them.) Cheers


I looked at them and still find – from the photo – rather filigrane for jeans. Maybe loafers are not so popular, where I live (too many thoughts of overweight poorly dressed tourists with cheap loafers, shorts and white socks spring into my mind), or it is just my own personal bias. I wear my two pairs (a tassel loafer loafer in dark brown suede and a mid-brown leather penny loafer) only in summer or late spring, preferably with cream or beige linen trousers.


Are you also from Vienna? Yes, loafers are very unusual there. Except for some gentlemen in their 70s. But I still find my loafers and my styling of them distinctly different from those older men and even more so from the tourists. (Btw: I feel that also our Austrian winters have gotten a lot warmer. The loads of snow that I remember from my childhood in the countryside are long gone.)


The loafer idea with jeans is interesting, but I would restrict it to plain suede with no tassels. I really like those Alden full strap loafers, but regular leather or cordovan is too shiny for this purpose in my opinion. So I’d wear those Aldens with nice chinos or linen pants only for example during the warmer months with or without socks depending on the venue of course.


I appreciate the perspective on loafers. I would be interested in an article devoted specifically to loafers. It’s something that you have been writing about more, and is particularly relevant given a more casual wardrobe. Loafers have come up in many contexts, and as a part of many other pieces, as well as reviews of different styles and makers. My thought would be something like a buying guide, where options, makers, price-points, and uses could be discussed. The idea would be for someone who is looking to buy a pair (or another pair), a summary of the different choices available.


Seconded. Something a step down from the Aldens (the price always gives me palpitations) but still durable. Love the look of the Horatio but Simon marked it down on its quality. Am I correct?


And maybe a paragraph about the different options: grain, suede, leather (tan especially) and cordovan colors: #4, #8, whiskey, and cigar.
I find the amount of options overwhelming, and I cant narrow it down to what I “really” want. Unlike with other types of shoes which I find it much easier.


Can anyone help with UK/London suppliers of Alden loafers? In particular the LHS; I see a lot of overseas online stockists are limited in where they can ship the shoes.


Drake’s got some Aldens too. One thing to add is that they all stock different widths of the LHS, so worth checking before buying. For example, Clutch only has narrow width LHS and End only has wide width LHS…and this is not entirely clear from the website.


Thank you, Simon.


Alden doesn’t allow overseas shipping for most stockists.


What about the 180 by J.M. Weston? Good with jeans?


This is only my personal opinion of course, but I feel like leather loafers with jeans are a bit of a stretch for me. Like the equivalent of trainers with a suit. I also kind of associate it with that old Italian Stallion moneyed, but not particularly tasteful, look, That’s probably unfair and limited to the Gucci loafer with gold buckles. Also I’m never sure in our cold climate, with leather loafers, whether sockless is just too naff or with socks is too formal

I think my first step on that ladder would be a soft suede penny loafer, which would be a step up from my casual canvas slip on shoes. Otherwise, for leather, I’m a big fan of Edward Green boots with jeans. Yes, less formal, but quite rugged and can be smart with a high shine (black) or an interesting patina (brown). I’m willing to be persuaded otherwise, so on my next trip to London, maybe it’s time for a suede loafer to be part of my wardrobe.


I do love this type of look – the Hermes popover is a great piece as well. I would recommend JM Weston loafers as a great silhouette to pair with jeans. Resolute Denim’s instagram channel shows great examples of pairing loafers with jeans in an ivy way. I think the fact that vintage jeans often have more of a mid rise and straight hip pairs well with the loafers also.

Aaron L

Suede brogues can perform a similar task (and have the added benefit of surviving the sand they put everywhere in the playgrounds I have to take my toddler to – the Alden’s got pretty scratched up…).
P.s. I’d still love to read a piece on toddler friendly tips.


Hi Simon , I really enjoyed this piece , one of my favourites so far and Its great to read that someone else is wearing jeans and loafers ! I’ve been wearing this combo since the early 90’s when I bought a pair of Gucci snaffle loafers in chocolate brown leather which was, massively influenced by large parts of my childhood and teenage years in Italy.
I wear Alden tassels too and have about 10 pairs, in cordovan and suede , with a few pairs from brooks brothers which are distinguishable from normal Alden by having heel foxing . Your picture of the cordovan full strap, inspired me to try that style and I have been very pleased with that model and now I want a cigar coloured pair of tassels .
I love jeans and wear them all the time with button downs, in a variety of materials , blue and white Oxford, denim ,linen, seersucker, chambray and some stripes , always with a box pleat , or a pique polo in marine , navy or white for the weekend. My London wardrobe is small and everything is frequently worn . I have some navy cashmere jumpers, a few Cushman sweatshirts in white and navy and some outerwear . Some would say my wardrobe is boringly unimaginative ,but its simple effective , comfortable and certainly not contrived .
Your comment about trainers/style and the infantilism on grown men is very true and there’s a lot of older men wearing the latest air Jordan/McQueen/colour combo shoes and more than likely own many pairs and to me they come across that are fighting to stay young stop ageing which is part of the hive/sheep mentality. Which if that’s what they want , great for them , live and let live.
I wouldn’t be seen dead in the same shoes as my teenage/twenty somethings ! And I don’t think I’m that old .
I own one pair of monochrome ecru converse 1970 chuck taylors and that’s enough for me .


And my wife thought I was crazy for having 3 pairs of Alden tassels in different colors. Aren’t the Brooks Brother’s ones great? I have mine in #8 shell. My favorite pair!


How do you feel about Belgravia loafers with jeans? I think you’ve worn this combination in the past, would you do so now?


Hi Simon,
Before reading this post, I had expected to see a mention of JM Weston famous 180 loafers, as you previously mentioned here:
A remark on the cultural dimension of this topic. French men, for instance, do not wear the Horsebit laofers, whereas or because, they are usually quite ubiquitous with older women. Even though, nowadays a brand such as Celine does offer them for men. But I guess, they are intended for foreigners.


thats it! thats what i like about my casual footwear ive realised…the ‘high front wall’. thanks for putting words to it. jmweston 180, allen edmond patriot, paraboots reims, even old skool vans slip ons.


I am somewhat of a loafer addict myself. I also think that with jeans, it’s useful to wear loafers with some personality. Of course suede, chunky or red brick soles, horse bit, unusual colors (I have 2 in green), spectators, or pebbled grained. Or even battered to death or close to. Anything to dispel the notion that you are wearing your semi-formal work shoes with your frayed and weathered jeans.


Simon, Please defend the style choice of cuffs / turn-ups on jeans. If the hems are simply folded up, why not have them hemmed to the correct length? Respectfully, to my eye, the look, with retro antecedents, I appreciate, seems effected for work wear. Thank you.


As someone who owns no sneakers, this is a very natural thing to do, particularly in spring or summer. I have two pairs of Crockett and Jones Harvards, in dark brown suede and cordovan, which I use almost interchangeably with this t shirt and jeans look.
As I write this I am wearing the same white t shirt and jeans, but with dark brown suede Chelsea boots.


Nice. I’ve worn suede loafers, suede chukkas and suede monks with jeans for as long as I can remember (since my 18th actually, I vividly remember my first pair of suede loafers) but I only started wearing my Alden cordovan tasseled loafers with jeans when I saw a very stylish gentleman pull this off in Hong Kong in the middle of the summer and without socks. In fact, this is the reason I went into Tassels to buy my first pair of Alden loafers a couple of days after that encounter! I think it works best when everything else is super casual, so a worn pair of jeans and a t-shirt or very casual shirt


Loafers with no socks (at least in Italy) is considered by punduits of classical style a mistake except for summer unlined models but cordovan shoes do not fall in this category


Was going to ask about this! I’ve always found the loafers and no socks too uncomfortable (apart from my Belgians, which I wear a lot). You always do invisible socks? What brand is your favorite? I’ve always found they slip down too often


One problem I found with wearing the Alden full straps is that invisible socks don’t really work due to the low vamp.

Tom in New Hampshire USA

There is an article in today’s Wall Street Journal on a pair of Levi’s from the 1880s that sold at a vintage auction in New Mexico for $76,000. There’s vintage. Then there’s vintage!

J Crewless

Each to their own, but there’s too much contrast in the formality equation between loafers and jeans.


a well written article, as always

just a question about the 5th pic from the top – I am struggling to “like” the denim cowboy cum Italian Stallion shoes look, especially when combined with the limp wrist posture

Can someone explain to me whether this is meant to be “ironic”?


‘….. is that it stops an older guy looking too young.’ I’m afraid I’d apply that phrase to the older guy who might do well to avoid having rips in his jeans. Even on women’s jeans, rips look like sprezzatura gone too far. But maybe I’m just old fashioned.


Simon – your timing on shoes with denim is either well researched or insanely coincidental with Mens fashion week being a showcase for the recent onslaught of influencers abandoning sneakers for chunky derby’s like the Alden 990 and others like it



What are your thoughts on horsebit loafers? For some reason, I’m finding them more and more appealing, especially in the black grain leather.

Also, where can I find a good pair of light wash jeans? In my opinion, the look is best executed with a lighter wash as compared to a dark wash or raw denim.


I have been in love with Alden tassel loafers, both with jeans and dressed up, for a few years now, ever since getting a pair in black calfskin 3-4 years ago. Recently I got a long lusted after pair in Shell Cordovan color #8; they are the famous Alden for Brooks Bros tassels, which have the foxing on the heel. These immediately became my favorite pair of shoes. For a long time, I had preferred the sleeker, slicker look of an Italian style penny loafer, but Aldens slowly crept to the top of the heap, and the beautiful deep burgundy of that #8 shell pushed it over the edge. I have worn them with all levels of tailoring, but especially love them with jeans and an unstructured blazer on the weekend. I have to say, though, they do look great with a suit as well.
Just as you say, they are a perfect amount of chunkiness, while also being fairly sharp, with the tassel being the only adornment on the shoe (besides the foxing on the BB pair). When I got my first pair of Alden’s tassels, I was surprised by how comfortable they are all day long; I think this is due to a relatively long vamp. Not coincidentally (as I wear one or another pair of them all the time), I am wearing my pair of black calfskin tassels by Alden today. I also have them in a light brown color as well, which also go great with denim.
Side note for Simon: great suede blouson! Very cool look. I appreciate the tip that a baggier fit is a good look, so long as it’s not too long of a piece. Excellent advice to heed!

Gary Mitchell

Im sitting dressed almost the same in Loafers, jeans and t-shirt. Im a fan of Real McCoys and now your tapered t-shirts but this week I bought a few t-shirts from Uniclo (always good for wear cheap alternate) to keep me going. Then I also bought a few (because I liked the colour) from Gu (Another Japanese(?) cheap shop) and sitting here in the tea-house I have just discovered they have no side seams! As thick/solid as RM and tube knitted all for around $10 or less…. Maybe it will fall to pieces when washed but then Uniclo dont so maybe this wont. Time will tell I guess.


I would have never thought jeans and loafers as particularly unexpected or groundbreaking, but the article and comments seem to suggest otherwise. I’m baffled.


simply because they have flat feet and have to travel long distances

William Kazak

As I have been understanding Ivy more and more I have been mostly wearing kakis/chinos instead of jeans. Now you are discussing wearing jeans again. Oh my. I gave up on wearing loafers years ago. They would not stay on my feet properly. Florsheim had loafers that had elastic inside that would keep the loafer taunt. Those worked for me back in the day.


I love the look of loafers, but alas, don’t own many, as most models don’t fit my feet well. The problem is probably quite common – high instep, slightly wide toes, narrow heel. I have, however, found a style that is incredibly comfortable, by the company, called Meermin. The loafers are completely unlined and incredibly soft, while still featuring the Goodyear welt construction method. What’s also worth noting is how incredibly versatile they are. Because they’re soft, they can be worn with more casual attire; however, their last is so elegant, they look perfect with tailored clothing and even a suit (unless the occasion is very formal, in which case I’d only wear oxfords). I wonder, why such a style is so difficult to find. So far I only know two or three brands that offer such soft, unlined, “unconstructed” dress shoes. I wonder if, perhaps, the style will become more popular, just like the “soft, unconstructed” tailoring has become mainstream, while only a decade or so ago, such soft tailoring was only available from custom tailors. I’m sure that if more young people tried wearing such incredibly comfortable shoes (it should be noted that any style of dress shoe can be built using the same soft, unlined design), they would certainly wear dress shoes, instead of sneakers or the horrendous “hybrid” styles we see everywhere these days. Speaking of hybrids, do you, Simon, believe it’s just a ridiculous fashion that will pass, or is it here to stay?


Give Alden loafers a try. If the heel slippage is too much try a heel pad.
I had a success with Carmina for my high instep, even thought the internet says the last is more suitable for low instep. The last is Uetam, but it’s more on the elegant side.


Thanks Simon for IVY insights into jeans and loafers.Its lovely to read your posts.

Any alternatives to Alden full strap loafers.
Alden is difficult to get especially in UK.


Anglo Italian has a full strap. They used to have it in color 8 cordovan too.


What is the pocket on the left chest of the popover? Is it a large pocket that just sits with the seam going across? Is there one on the right or is it just closed?


Sorry, my loafer knowledge is poor but I am wondering whether an Edward Green Picadilly in Mink suede would work with jeans, or is it too smart/pointy? If not, is there an Edward Green loafer better suited to this sort of style?


Hi Simon, love your take on this. It’s very topical for me as I have just started wearing this look too. Do you have any thoughts / rules around socks vs no socks with this look? Also do you prefer a cuff or no cuff? And how long should the cuff be? Presumably less fussy compared to trousers but keen to hear your thoughts.


Looking forward to it!


Simon, a great article, really enjoyed reading it.
A question: would you ever wear a tassel loafer with black tie? E.g. a highly buffed slim black cordovan?
Another question: do you ever wear a classic Barbour, e.g. Bedale or Beaufort? They appear a good match for the jeans-loafer outfits.


Thanks. I can see it being deliberately unusual, but to my eye not more than opera pumps, which I know are super traditional but still look a bit weird and deliberately different today.
Yeah the Wax Walker fits the same bill and do go better with boots, although I do wear a Barbour more often, it’s my main casual jacket in late autumn and early winter and spring.


I’ve been doing this as well, though not really as a conscious decision, more like, “I don’t feel like wearing sneakers, what’s the most casual shoe that I can wear with jeans”.
Mostly because it was (and still is) too warm for boots. I’ve worn canvas sneakers a bit in summer, but for the most part loafers, tassel or belgian (dislike pennies).
I guess I bought the minimalist leather sneakers trend, because I remember I was excited to acquire a first pair (which turned out not fitting too well), then second, then considered replacing the first. But actually meanwhile I had started wearing welted shoes exclusively in the office, and got used to them to the point I now feel most sneakers are too flat, with no heel. So in the weekend I mostly ended up wearing loafers instead.

Jasper Smit

Hello Simon, just wondering since you mentioned what you put on early in the morning… Don’t you dress a lot more casual in general since you have kids? I pretty much only wear sneakers, jeans and flat front chino’s. I enjoy it a lot because I still wear quality pieces and find it fun to try different things. But having kids really changed my way of dressing a lot.. Wondering what your experience is. Thanks.


Hi Simon

I read all of the topics on your page regarding Alden and it’s very informative.
For long time I wanted to buy Alden Aberdeen last tassel loafer and split toe 2210. But I am very confused about the width.
crockett and jones cavendish fits me very well but Edward green Belgravia is bit tight on the arch.
I am wondering if you could suggest me from you experience which width of Alden teasel loafer should I order.
I do apologise for any inconvenience if it may cause. My size is uk 9E for EG & C&J

Kind regards


Hi Simon,
There are two things I found especially interesting about this article.
First of all, I like your loafer and jeans look. I think, at times, we who enjoy clothes can get too bogged down in the minutiae: Last is too slim for jeans! Tassels aren’t casual enough! Jeans are workwear so they shouldn’t be “dressed up”. And on and on. Isn’t there a saying about those who know a lot about wine know everything except how to enjoy it? I think sometimes it’s the same thing for clothes.
Jeans are easy. Loafers are easy. No need to overthink it. It all makes for a relaxed, yet elegant, ensemble which you have ably demonstrated.
Secondly, you made an excellent point when you said the look “stops an older guy from looking too young”. I think a lot of guys fear looking (or being) old or stodgy and that keeps them from embracing more classic (and often much more flattering) clothing, which is a shame.


Hi Simon,

Thank you for another great post. Partially because of it I made the decision to pull the trigger and buy a brown cordovan Harvard from Crockett Jones. I’m having a bit of a challenge finding good socks to pair it with. I like the cream/ecru but I find it hard finding one these days (mes chaussetes rouges and Berg&Berg are out of stock), so would you recommend a place to buy them?
Also if you have a recommendation on which socks to pair with the shoes besides the ecru, I’m all ears!
Last thing, when you say you pair the shoes with white socks, are they truly white or off white?



Thanks Simon!

If I may still ask: does you mid calf socks not often fall? I feel that all that I previously had ended up falling after a short while, which I don’t find is an appealing look. Does it not happen often with the Rototo socks for you (fyi, mine weren’t from Rototo)



Why? The top isn’t visible for both otc and mid-calf socks anyways?


Hm, I agree for sneakers, where I also prefer to wear retro sport socks, but for any other outfit with long pants and decent shoes – lets say jeans and loafers as the most casual variant – do you really believe a generic pair of socks like these (https://www.falke.com/uk_en/p/bristol-pure-men-knee-high-socks/15415_3000/) would look “out of place”?
For the sake of a simple wardrobe, I have for a long time limited my socks to identical navy and dark grey OTC socks, some off white sport socks, and some invisible socks for shorts weather, and I feel this has served me well.


Interesting, I guess it’s a personal thing. Regarding appearance, with jeans trouser legs don’t move up a lot anyways so I guess it doesn’t matter. But just to be sure: when wearing chinos with loafers, you want your skin to be visible when crossing your legs? That sounds a little odd to me.


Sorry to insist, I am afraid i don’t understand. Are you suggesting only a tiny proportion of men wear otc socks? Because to me whenever I go to a sock shop it seems rather like at least a third of their offerings is otc. Also, the combination I suggest looks exactly like this (https://www.permanentstyle.com/2019/09/how-great-things-age-the-belgravia-loafer-from-edward-green.html) – aren’t these otc? And otherwise what you are suggesting are midcalf socks that however sit high enough to not reveal any skin?

Magic Dragon

In the article, you commented they were Bresciani knee-length socks from Mes Chaussettes Rouges though.
I support your shift in preferences — they don’t look great with jean and Belgravia.

Amrinder Saraogi

How about this kind of loafers with same outfit of t shirt and jeans?

Amrinder Saraogi

This is my first time investing in a nice pair of shoes and therefore wanted to be sure about the purchase.
1) When we talk about smart slim suede penny loafers then do this shoe fulfill that criteria in terms of its design and structure?
2) Is there any flaw which you could point out if possible by looking at the image?

Amrinder Saraogi

Just received my loafers and while trying it out with t shirt and jeans the combination becomes a little smart but at the same time it also come out more matured. Quite happy with that look. A couple of questions if you could answer.
1) Would you rate the cardovan tassel loafer and your dark brown suede Edward green loafer on the same scale in terms of formality?
2) Your opinion on combination of polo t shirt, mid blue jeans and smart suede loafers?


Hi Simon,

Thanks for this post – great read. I was recently reviewing your “If you only had five shoes” article and note your fourth item was a black leather penny loafer. Would this still work in your above examples or would the black clash in this instance? I’m interested in picking up a pair of black leather loafers to compliment my brown tassel pair.

Kind regards,

Josh Lee

Wow! I’ve been wearing the Alden Cordovan loafer just like yours with my dark selvage jeans lately AND my dad had the exact same Hermes Suede popover shirt.
I remember “borrowing” it a couple of times when I was in high school.
Thanks for reminding me of the past.
Made me think back in time again.


What would you say to wearing Edward Green’s Piccadilly loafers in antique oak with a pair of jeans? Too formal do you think? I have almost completely stopped wearing suits or formal clothing since I no longer work in an office, but have these lying around. The rest of my loafers are casual. Not sure what to do with them though. Pic is from Google, not my pair. Same colour though…

Bob Muscat

Simon – to be clear, would you feel ok with an Alden 986 cordovan penny loafer in this case? I was considering those or LHS suedes, but I already wear suede chukka boots and wanted a little more diversity in footwear.


Hi Simon,

Are your two pairs of Alden’s in the same size? The Cigar tassels look like a more comfortable fit than the full strap penny’s so I wanted to get your thoughts on sizing! Thanks.


Interesting. I’ve done the same with my latest tassel loafer and I do get a more loose fit, especially in the collar, like yours above. While this is the case, the length is actually more correct.

Alden Fan

Hello Simon,

How do you feel about the collar gape/flaring on your tassel loafers, especially prominent in the second image in the article? Is this something that is determined by the width of the shoe and how much heel slip do you experience on this pair vs. the pair a half size down?

Alden Fan

I might try going down a C width next time. Have you ever used tongue pads?

Joe P

Hi Simon, have you ever had to get any of your Aldens resoled? If so, who did you use?

I understand Trunk can arrange for them to go back to Alden, which would obviously be ideal, but is expensive and slow. I’m based in London and can get to the places you recommend in the ‘repair’ part of the site – but the look of the welt is such a key element to an Alden and I worry they’d just do it as a standard resole.

Thanks in advance.

Joe P

Thank you!


Dear Simon! Do you know how the tassel loafers from Anglo Italian (made by Crockett) compare to something like the ones from Alden? From what I can see online I would guess the AI ones are slightly more sleek? Still casual enough for jeans but maybe better with casual tailoring than the Alden. I guess there are no big quality differences between crockett and Alden since in the US Alden shoes are not really more expensive. Am I right? Thank you!


Yes, I had the Aberdeen last in mind. Thanks


Do you have a recommendation for a
Slightly slimmer loafer with a wide toe box. I am currently wearing the Boston, in a EE fitting, and it still pinches my little toe.