Baseball cap, white jeans and Ivy: Pick and choose

||- Begin Content -||

There are five elements I want to talk about in this outfit. Five. 

And I’ll take them all separately - because you can easily change one, or only like one. There’s no need to lift an outfit (or, give it the thumbs up/down) as a whole. 

In fact I’m often surprised when readers don’t automatically do this. Most outfits have several ideas in them, and it’s unlikely all of them will appeal. (Or that you’ll have the clothes to make use of them all.) 

Most brand lookbooks or window displays are even done this way deliberately - containing a half dozen ideas in the hope that at least one will hit home. 

I’d never wear a Ralph Lauren look head-to-toe. But every window display has something - usually how two items are combined together - that I’m interested to take and try. 

First, the cap. Because to the PS reader it’s probably what stands out. 

I’ve worn and shown my old Berkeley cap several times in the past, but perhaps never with remotely smart clothing. I increasingly like it for the way it casualises (if that’s a word) an outfit, adding a taste of American sportswear and subverting some expectations of classic clothing.  

It’s not quite the contrast of high/low dressing - that would be wearing the cap with a suit and tie, and I wouldn’t do that personally. Rather, I like it with pieces that sit someway between casual and formal: a raglan coat rather than a tailored overcoat (smart) or a blouson (casual); and suede boots or loafers, rather than oxfords or trainers. 

Of course, wearing a baseball cap with luxury casualwear is something Americans have done for a long time (though with mixed results) - and I like it with accompanying clothes that are simple and considered.

Interestingly, I find this old Berkeley cap looks a lot better than my other favourite - the RRL suede. I think it’s because the beaten-up cotton makes no pretensions to being smart, where the suede perhaps does. Beware ‘luxury’ baseball caps for similar reasons. 

If you dislike the cap, it could easily be swapped for a watch cap/beanie - perhaps in grey. 

Second, the yellow shetland. 

I said pretty much everything there is to say on this colour here, when discussing strong colour in accessories. 

For now, suffice it to say that the shetland fluff adds to a certain Ivy feel. And that it could easily be swapped for navy, grey or olive to achieve something subtler. 

Third, the white jeans (or actually cream - much better). 

I find this denim increasingly useful because, on the one hand, cream goes with everything. Every colour of jacket, every colour of coat. This comes up whenever we discuss trousers to go with odd jackets. 

The downside of cream is that it can be showy and impractical. Unless you live somewhere very sunny, and don’t mind a large cleaning bill. 

Denim mitigates both these dangers: because jeans are more everyday, and because they can take a little dirt without looking actually dirty. They’re also easy to scrub a little if needed. 

Still, I wouldn’t wear white jeans in the rain. They’re impractical and they look it. 

If white jeans will always be too eurotrash for you, they could be swapped for regular denim or grey flannels. 

Fourth, brown-suede loafers. I mentioned that these were next on my wishlist when I covered my brown-calf Belgravias

Here they are, and they are certainly the most versatile shoe I own. Nothing else could go with every jean and chino, with flannel and a lot worsted.

That’s all I have to say on the subject. Except you could swap them for suede boots or (if that’s your style) slim-line trainers. 

Fifth and last, I think looks like this are inspired by writing about Ivy style - despite denim being anathema to the Ivy purist. 

The spirit feels similar because of the combination of smart (shirt, loafer) with more casual (cap, jeans). The jeans would have been chinos originally, of course, but in this colour they do a similar job. 

We covered Ivy a little with the Ivy Style Symposium last year, but I’ve also interviewed a few people from around the industry for an article on the subject for the Financial Times (which will be out in April). 

One thing everyone emphasised was that Ivy was always about mixing styles, and doing so in a fun, irreverent way. It’s the look it makes least sense to be hardline about. 

I think combinations like this do something similar, and it’s something I’ll mine myself further in the future, I think. As I mentioned during the Symposium, everyone today seems to want to combine sportswear with more formal clothing - but often with horrible results. Ivy has some much more attractive alternatives. 


  • Baseball cap, gift
  • Raglan donegal coat, Cordings
  • Yellow shetland sweater, Trunk
  • Blue oxford shirt, Permanent Style
  • White jeans, Levi's Lot 1 bespoke
  • Brown-suede loafers, Edward Green (Belgravia)

Photography: Alex Natt

Notify of

Inline Feedbacks
View all comments

Hi Simon

Is Garbadine cotton jacket a hardy? Would it be good for daily wear?

Thanks for your advice


I got a rollneck in the same colour last year. The colour is actually surprisingly versatile. I even wore it with the PS trench coat on some occasions.


Really good article that appeals across the board.

Reference Cordings , on visits to London I always enjoy visiting the shop and browsing.
But find the sizing and style ‘age’ the wearer.
For example their chinos in beautiful rich colours made in a heavy cloth could do with some tapering.
Shops like these should be encouraged to offer a good alteration service which I believe would result in them having a wider appeal.

How did we come to lose the in-house tailoring service ? Maybe this is how ships could encourage customers to move away from internet purchases and to more personally visiting the shop and having items pinned and altered to fit ?


Completely agree
The only items that I think work from their (for a younger look) is knitwear (which is very reasonably priced) and over coats which can look good in an oversized way. Simon demonstrates this here and I bought a navy loden from them this winter that I can wear with trainers and denim or a suit.


About a year ago Cordings altered a pair of molskin trousers. They have for years. 10 GBP for a cuff and another 10 to taper (as I recall). I’m surprised to hear they’ve dropped that service. (did you inquire?)


Cordings have an excellent tailoring service. I’ve had two pairs of trousers altered and they did a very good job


As a loyal and regular Cordings customer for over 20 years, your comment surprises me. The chinos are, and always have been, a classic cut and fit. Only men with thin or puny legs would need to taper them. An Italian cut would probably suit you better,

Cordings’ “in-house” tailoring service, and I have used it several times, has always been out-sourced to a local tailor. It has not been “lost” and it would be useful to know why you believe that it has. A good alterations tailor should be able to provide a similar service.

Robert M

Very good comment on assessing parts of the outfit separately.

For me the cap is a big no-no. In general I don’t consider it flattering on any head and unfortunately it reminds me of these guys one sees everywhere who would have, say, a nice suit, but ruin it with poor accessories or shoes. But also in this particular combination, as I think it looks a bit weird with a knee-length coat and nice loafers, even though I’m all for mixing the levels of formality.

The rest of the outfit, though, I like very much. Even the white jeans, something I would never wear personally. The sweater colour is splendid too. Overall, it’s great to see you experimenting even when some items might not be my favourites.


Like Robert, I can’t say that I’d wear the hat but I do admit that on cold days I do want something to give my hair a hand at keeping me warm.

I think I would also swap the trousers. I don’t think white/cream jeans would see enough wear to merit a spot in my wardrobe so I’d have flannel or perhaps a pair of chinos instead.

I absolutely love the jumper and coat combination. I also loved the bright scarf you paired with a brown coat in a different article so perhaps it’s time for me to pick something up to give that splash of colour.

Suede loafers are also on my purchase list but I think I prefer the Piccadilly model. Not sure I’m mentally ready for tassels from a style perspective and I have visions of a toddler casually destroying them in a moment of experimentation


This made me laugh aloud at the realism. So funny, so true.


I really like the idea of ‚casualising‘ a semi-smart outfit with a baseball cap and have been doing this for quite some time, but the one thing that keeps me from doing this more often is that the cap messes up your hair, which means that it can only be worn on occasions where you‘re not expected to take it off, such as running errands (or attending an actual baseball game).

Peter K

This fellow baldy agrees.

If anything, going bald make s some sort of cap or hat necessary in colder weather (for warmth) and bright sun (to prevent sunburn).


I got a Drake’s beanie recently in navy and it’s super, goes with everything. I absolutely love the yellow shetland sweater, and the white / cream jeans are great. I saw your Donegal overcoat in another post and think it’s gorgeous. The white / yellow / brown combo is great. I also enjoyed – being from Ireland – how Donegal tweed seems to be getting its due a little bit more nowadays. Scotland in Harris tweed and Scotch has managed to promote itself better than Irish whiskey and tweeds, unfortunately, though there’s room for both. (I have a Harris tweed overcoat and I’m not too partisan, btw.) Happy too to see SEH Kelly’s interesting Donegal tweed Balmacaan, which is out of rotation at the moment. Finally, living in NYC, I see a lot of the “baseball cap with a suit” look – it’s mainly either young guys who’d rather not be formally dressed (suit jackets too short and too tight, etc.) or men in their 60s who rock it better, but I find the casual Ivy look to be the best way of wearing it, most definitely.


Good timing, I have an appointment booked in with the Lot1 Team. I’m thinking of getting a cream denim like the one you are wearing- is there only one cream colour they offer? Do you rememeber what yours are?


Excellent article. This is very useful styling guidance / inspiration around mixing items up in a cohesive manner. I feel a lot more comfortable (literally and figuratively) about incorporating slim line trainers, which for me is good when a day out involves a lot of walking!


Baseball cap !

No, never ever.

Unless you’re on a baseball diamond or a golf course. Maybe fishing.


Great outfit apart from the cap.

The wearing of caps (and in particular, faux-vintage ones) with tailoring is a messy look. Drake’s and its disciples have been pushing it quite hard of late. P Johnson as well. It is not stylish at all. As you say, a beanie would be much better.


I think the baseball cap has been quite heavily pushed by almost all major fashion houses for the past few years. Balenciaga, Gucci, Prada, you name it. Even fashion houses that wouldn’t normally do baseball hats, are doing it. And they’ve all been using it with formal/smarter wear. Resurgence almost certainly inspired by the MAGA hat look.


Agree totally; don’t wear baseball caps unless you are playing baseball.

Also disagree Simon with your comment that Americans tend to wear them with luxury leisurewear. As a longe term East coast resident, I would conclude that most Americans would not know what luxury leisurewear actually was.


I didn’t say most Americans wear them with luxury leisurewear either; I said most Americans wouldn’t know what luxury leisurewear was!!

Simon C (not Crompton)

What a fantastic article. Many times I have ‘stolen’ parts of outfits from lookbooks and indeed many PS articles. Nice to see reference to cream/white denim. I think it works very well in the winter but, as you say Simon, be prepared for a hefty cleaning bill thanks to the wet Manchester weather. And work colleagues taking the p*** out of you as they are a bunch of philistines.

Paul Boileau

Not a fan of the baseball cap but the rest of the outfit is on point. The jumper provides a nice pop of colour. I’ve noticed Alexander Kraft likes to rock the white trou but usually in more exotic locations than London town in March!

Daniel Ippolito

Hi Simon! Just out of curiosity, why should any of us want to “subvert the expectations of classic clothing”? Isn’t subversiveness for its own sake a tad juvenile? i ask without any intention of offending…


Also it’s fun to play.


Classic clothing, if fitted correctly and worn well, does not make the wearer look old fashioned, stuffy, too old etc. In fact, it makes him look elegant, urbane, interesting, and masculine, all good things. Does Daniel Craig look too old or stuffy in a suit? Absolutely not, actually quite the opposite, he looks like a real man. I’ve never seen you look stuffy or old fashioned in your suits, but rather very elegant, savvy, and adult. Men should be wearing more tailored, classic clothing not less because they look great in it.


It’s a shame that the one film where Craig’s suits appear to fit him – and don’t make him look like a gorilla stuffed into a tuxedo – also happens to be the worst of the bunch.


Yes Mr. Craig’s suits are too tight unfortunately because that’s the look the costume designer wanted for some odd reason. Setting that fact aside, he doesn’t look old fashioned or too old. My larger point is that most men look so much better well dressed than poorly dressed. Now this idea is obviously rejected by a large swath of the male population to their detriment in my view. Men in general would be so much better off if they stayed tailored more often and the women in their lives would appreciate it as well.

Daniel Ippolito

Hi Simon! I agree with you re: Daniel Craig – his suits are too short and too tight and he looks like a middle-aged hipster trying too hard to be fashionable. Most of the other Bonds, however, looked terrific in their traditional suits, and Roger Moore even managed to look good in his 70’s inspired outfits (with a couple of exceptions.) I have to diagree with you re: “culture and society and the impression we give with clothing”, however. Considering the amount of time and effort that some people invest in sprezzatura, wouldn’t real sprezzatura consist of wearing classically tailored clothing regardless of the general slobbification of the culture? I am a university professor in the US and wear a blazer or sportcoat WITH A TIE every day when I go to work, and I wear a blazer or a suit every Sunday when I go to church. I am in a small minority in both sets of circumstances, but I don’t care and I dress the way I do because (1) I enjoy it, (2) I am a grownup, and (3) I am a professional and am not ashamed to appear as such. When grown men dress like teenagers in their hoodies and cargo pants, they are also more likely to behave like teenagers. Studies have indicated that very casual workplaces tend to have lower productivity and a higher incidence of sexual harassment, which makes perfect sense. If people go to work dressed as if they were going to a happy hour at a beach resort, they are more likely to BEHAVE as if they were at a happy hour at a beach resort.


May i ask what you mean by “safe places”? What would constitute an “unsafe place” in your opinion?


The best comment on this thread professor, thank you.


If enough of us decided to resist “the power of cultural association” then maybe it would cease being so powerful!


True and it would be wonderful. I’m so tired of seeing grown men dress like teenagers on purpose or because they don’t care, having no respect for those around them. That’s not culture, that’s chaos and it needs to stop.


Great article. I have a cream Jean (nw3 from Blackhorselane) and I agree with your points. Funny enough I also sometimes pair it with a yellow sport coat, I think it works very well. But as much as I like cream trousers in winter, the slush and salt stain make them a pain to wear (it leaves black stain which are very visible on a cream Jean).

Evan Everhart

Hi Simon,

I love this. I am an Ivy enthusiast as you, I am sure, are aware, and I have many friends and acquaintances who practice the baseball cap with tailoring quirk. Typically with something like a blazer and wrinkled, un-creased chinos and a chunky OCBD.

It is not my personal taste. I do wear caps, but typically just my favorite cap, which is a moss green corduroy trucker model with an embroidered pheasant in flight on the front. I wear it while fishing or sometimes casually shooting. I actually liked it so much that I bought two. The first one is already wonderfully weathered.

The top coat is Gorgeous! My salutations!

As to the trousers; I would have gone for cream chinos. I still have my Father’s PRL Prospect model in that color. I like them.

Finally, I love the sweater and have been seeking a yellow Shetland at a reasonable price for some time. Hopefully I find one soon.

The shoes are outstanding as you know. Thumbs up!

I have enjoyed this article, as most of yrs, Simon! Thanks for sharing yr unique perspective, as always.

Evan Everhart

Hi Simon,

I will post a picture of one, the other, or both in reply to one of yr Facebook postings as that will likely be easiest. The PRL Prospects are my favorite model of his trousers. I wish that they still made them. I get the odd pair off of Ebay as I find them. I have most of the colors in 4 different sizes at present; 34×30, 33×30, 32×30, and due to my most recent weight loss, I will have to start looking at 31x30s soon…..luckily used PRL chinos are relatively cheap. The cream ones are charming. I have them put away for the Winter however. I’ll look for them.

Have a Great Day, Simon! 🙂

Evan Everhart

I pulled the caps at least out from my closet where they sit with my other hats and caps, and posted a photograph in reply to this article on Facebook last night. You can see the dramatic patination which the hat has taken over the many years that I’ve worn it in inclement weather while out shooting and spending time in the mountains and country with my family. I got that hat perhaps 10 or 12 years ago and I think the side by side is dramatic!

Evan Everhart

Hi Simon,

Below should be a link to an image of the hat, roughly as it looked when I originally purchased mine, though mine had a mellower, softer, and richer green.
comment image&exph=400&expw=379&q=green+corduroy+pheasant+trucker+hat&selectedindex=20&ajaxhist=0&vt=0&eim=0,1,2,3,4,6,8,10


The baseball cap and sweater colour give a very American look. Apologies but that’s not meant as a compliment.


Good to see some stylistic diversification. The colors coordinate well. The loafers seem out of place to me. A pair of Onitsukas, for instance, would bettter compliment the cap.


Goodness, I was wearing an almost identical outfit a couple of weeks ago. Same jumper, shirt and jeans from Lot1. Coat was a brown Rubinacci Casentino and the shoes were different, that’s all.

Great minds……?


Hi Simon,
Regarding the loafers comment, “ Here they are, and they are certainly the most versatile shoe I own.” Of course, you explain that they can match all jeans and chinos you own but I’m curious to know if this is a recent revelation or if you have always considered the suede tassels as so versatile. Of course, they’ve become ubiquitous among the #menswear elite for some time as all of them seem to wear them nearly exclusively.

I agree that the Belgraves are beautiful so for an individual with such a strong grasp on his personal style such as yourself I just find it interesting that it’s taken you so long to make such a purchase.

The overall outfit is superb, by the way! As an American I can certainly identify with this combination with such classical Ivy stylings.


One of your finest if you ask me. I think part of why this combination works so well is that the hat and jeans (both cream-ish), and the coat and loafers (both brown-ish) play quite nicely together making the outfit feel more coherent. Essentially, you have a lot of pieces but have prevented it from feeling too busy by narrowing the number of colors involved.

I also like the hat. Makes me wonder if I should get one from my alma mater. It’s certainly a lot cheaper than other menswear purchases.


Some years ago my wife was jogging in the Royal Botanic Gardens, Sydney, wearing her Cal cap. From some distance a man’s voiced bellowed “Go Bears”. Simon, as a heads up, should you encounter a U.C. Berkeley fan in your travels the appropriate response is also “Go Bears”.


“If you dislike the cap, it could easily be swapped for a watch cap/beanie – perhaps in grey.”

I must admit to disliking baseball caps but a beanie is just as bad. A flat cap or trilby would look much more stylish.


Simon, from what I gather you are not a big fan of belts in general. But if you would wear a belt with this outfit, what kind of belt? Dark brown suede to match the loafers maybe is first that comes to mind for me, but I ask because I find that the contrast between white jeans and dark belt is too much and would like to hear your thoughts. Thank you for great content as usual.

John Edmund

Baseball cap and cream/white jeans – please no! To be serious, the whole outfit calls out for a Fedora.


Great! First the lilac shirt, now the yellow sweater. And I thought I wouldn’t wear them… Please, try some more colors – those posts are quite unique. Nobody else seems to pull them off so well.


Unfortunately although the baseball cap is one of the few hats that suit me, that picture of Williams Hague being “casual” has ruined it for me….


Interesting how one piece can have such a sizeable impact – if you replaced the baseball cap with a watch cap, nobody would give it a second thought. I feel that baseball caps (and apologies if this comes across as derogatory to anybody who enjoys wearing them) have a curiously infantilising effect on the subject.


Amazing! I immediately ordered that exact sweater after reading this.

You’re a great inspiration, keep up the tremendous work.


I’d delete the word ‘luxury’ here: “Beware ‘luxury’ baseball caps for similar reasons.” I find nothing good about them except purely as a practical step to shade your eyes from the sun where a brimmed hat (which also shades other parts) is a bit cumbersome to lug around. They’re a stylistic disaster, like sneakers with white socks and shorts on men, especially mid-to-old ones (like me).
Second, the jeans. They’re fine except that strange little turn-up/cuff. It’s odd, and too small to be of much use – it looks like an afterthought. It also makes the helm flare out a bit and gives the impression that the trousers are simply too short (IMO the tighter the bottom opening is, the shorter you can go – these are not especially tight at the bottom).
The rest, especially the sweater, all lovely.


Agreed! There’s no such thing as a luxury baseball cap. These caps are fine when involved in outdoor activities or at the beach, but should be avoided otherwise. I know a woman whose then husband refused her request to take off his baseball cap as they were going inside to a nice restaurant for dinner. That was the last straw for her and she divorced him shortly thereafter. So sartorial faux pas can have real life consequences. Mostly though wearing baseball caps just makes grown men look juvenile.


@Scott. That was a heck of a story!

I know a lot of men who have issues with thinning hair.
Just grow old graciously I tell them.
Thinning hair says : mature and sexy.
Toupees and hair transplants just look weird and immature.

I know a baseball cap is frowned upon in most indoor places. I dont ever wear them at all.
But I guess she wasnt a keeper either.


I would personally not wear a baseball cap, unless playing or watching sport. The imagery is not good; worn sideways or backwards they say entirely the wrong thing.

Attaching sunglasses above the rim, as cricketers often do, looks even more sillier.


I love the overall look.
The cap goes fine with it, a beanie I guess is more expected, especially in the cold (I’ve never understood the idea of wearing anything for warmth that doesn’t actually cover your head and ears).

Those cream denim’s are really nice and works very well with the tweed raglan. It’s like a Sunday version of the white cavalry twill and liverano look you did at Pitti.

Henry R Mandell

Cap tip to you Simon, for elevating the ubiquitous baseball (actually ubiquitous trucker cap) to a fashion statement. The pairing goes well beyond the white (though impractical) slacks. It’s a great mix of casual with old school, classic materials and style.

The truth be told, especially out in Los Angeles, where I live, not much attention is paid to luxury casual clothing, or it is confused with overpriced casual clothing. I sadly dust off my collection of Italian or semi-bespoke suits because I no longer have anywhere to wear them.


My takeaway: you’re handsome enough and still young enough to get away with just about anything. Most men wouldn’t be able to pull this off.

On a related topic: after I saw too many portly middle-aged Roman men out to dinner in blue jeans and navy blue blazers I came up with the following rule: don’t wear blue jeans after the age 50 unless you’re riding the range, hammering nails or are Ralph Lauren.


Like the overall look, fabric and colour combinations Simon. Maybe it’s my age but I don’t see the appeal of jeans or chinos with casual turn ups rolled up by hand I guess. Appreciate your thoughts re the appeal ? Thanks


I have never understood the compromise between climate and color.
Why do we have to match cold climates with dark and gloomy outfits?
That notion was acceptable in the days of the industrial revolution and coal economies. Lets have a bit of fun. The color selection you chose was superb.
A French beret Or a British flat cap would have been a preferable choice, imho, but that is just me.

Baseball caps and shorts are items reserved for children and young men.


I would imagine for most people the compromise is largely a practical one. In the last two months the UK has had record levels of rainfall – splashing about in light coloured denim/chinos/trousers tends to show up water stains something fierce.


Check out photos of 1960s California beach and car culture, white pants all over the place. I wear denim and love it paired with natural suede shoes and boots. Hats are a necessity in Southwest U.S.


Hi Simon! Can I please know the weight and leg opening of the white jeans? Thank you


i bought a pair of white jeans last summer – I´ve been wearing them with a blue oxford (and a green overshirt) or a grey sweater. (and suede, dark brown desert boots).
But do you think I could change the shirt to a e.i. a khaki coloured (and change the outer layer to blue)


HI Simon,

Great post, I wondering any recommend cream jeans on top of your head? It’s quite a challenge to find a RTW one. Most of them are just dead-white.



Simon, what size do you take in the Trunk shetlands? Thanks


Hello, I hope you’ll notice my comment. I’m wondering about sizing of the Trunk Berwick Sweater. Would you say it runs big or small? Should one take into account that the wool might “loosens up” a bit over time?


Would you say that cream denim replaced cream trousers for you? I always wanted to get a bespoke pair, but this seems more and more impractical. Cream trousers might not clash with anything, but they seems quite unusual and old fashioned – and not in a way I like. Cream jeans, on the other hand, have worked for me well. Both as a casual option and with sportcoats, though maybe not for rain and snow.


Hi Simon can you tell what size is your Cordings coat? I am guessing quite small given their usual fit