Casual chic: The inspiration of vintage leisure and sportswear

Monday, February 15th 2021
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The origins of the ‘casual chic’ look we’ve discussed in recent months - which I see as a route forward for relaxed yet smart menswear - can perhaps be seen in the leisure and sportswear of the 1930s. 

That era saw the growth of leisure pursuits, and the clothes they necessitated. Sports shirts were added to dress shirts, sports shoes to dress shoes. And yet, the elegant, considered look of formal clothing was largely retained. It was casual chic. 

Utility became more important, particularly in the US, which always saw itself as a more practical society. And at the same time mass manufacture made the resulting clothes more available. 

The most obvious change was the introduction of knitted, collared shirts - what we would call  polo shirts today. But they had little in common with most modern polos. They were fully fashioned, with stand collars, fitted like a shirt, and worn tucked in. 

Basically they were an alternative to a dress shirt - not a T-shirt - for more active pursuits, and so made and styled in the same way. 

Trousers still looked like trousers. They were made in the same fashion, just perhaps a little fuller legged or in more robust materials. 

But we notice the trousers more in these old images, because the lack of jacket and waistcoat brings them to the forefront. 

There were soft jackets worn over the top - unstructured, natural-shouldered - but also shirt-jackets, and knitwear intended as outerwear.

Over the years the genteel sports that became popular in that era - tennis, golf, skiing - slowly moved from jackets and ties, to knits and shirts, to polos and shorts. But there’s always a point where the clothes were practical - no longer approximate to a suit - yet elegant. 

During the next couple of decades, this look drifted down into simple, off-duty clothing. 

One of my favourite images of this is the one above, of French actor Jean Gabin and friends in 1945. It almost looks like it’s staged to show a range of leisure-wear options. 

There’s a knitted polo (bottom right), a variation with no placket (centre right), a sports shirt with jacket (back) and to cap it all, Gabin himself in roll neck and button-through shirt-jacket. All with tailored trousers. 

Designer Scott Simpson alerted me to this image, and we chatted about it for this piece. “I love how relaxed and comfortable everyone looks, and yet still how considered,” says Scott.

“Gabin is clearly the best dresser though. Look at the elegance of that little jacket with the reverse-pleat pockets, and the full-cut pleated trousers.” 

I’ve talked in the past many times about how the principles of tailoring we discuss can be applied to casual clothing, but it’s particularly evident in these old shots. 

The higher rise of the trousers lengthens the legs; the tucked-in polo emphasises the waist; the polo collar frames the face. It all becomes more important, rather than less, without a jacket. 

That doesn’t mean everyone should wear trousers on their natural waist, or tuck in their polo shirt. I don’t do the former, and rarely the latter.

It just illustrates the power of line, and proportion. 

It might encourage you to consider a slightly higher rise, for example, or wear a more tailored trouser with otherwise casual clothing. Perhaps seek out a polo that’s cut a little shorter, even if you wear it tucked out. Shoes can be refined too, even if they’re trainers. 

Two examples of how I wear this are below, from recent articles - the first from this one on Baudoin & Lange Ginkgos, the second from this on summer dressing

“I think the most important things for people to think about are lines and texture,” says Scott. “There are sometimes fun things going on in these photos - patterns, probably colour we can’t see - but it’s all controlled by the cut and the feel of the clothes.”

I tend to wear this look in simple, refined colours - smarter, basically, and more akin to the palette of formal tailoring. 

But it doesn’t have to be that way. You can still have colour and personality - just keep your eye on the cut and the quality. 

Scott’s own clothing obviously has some good examples. I wouldn’t wear most of his strongly patterned shirts and knits, but I’d love simpler versions, in those styles. 

The polo shirts Drake’s was selling last year - knitted, fitted, stand collar - were another good example, and not too dissimilar to the old advertisement below. Bryceland’s ‘sportswear’ is similar too, and like Scott directly inspired by vintage pieces. 

Plus many of the brands mentioned in the original ‘casual chic’ article - Adret, Connolly, Rubato etc. 

Of course, the old illustrations from Esquire or Apparel Arts are useful here too. I particularly like the two below, both proposing the knitted jacket as an elegant alternative to tailoring for sportswear. 

There are a lot of different designs and colours in there, but they all have a similar idea of cut and proportion. Some jackets are a little longer, some shorter; some a little bigger in the chest, some neater; but they clearly hold similar ideals of male proportion.

The only problem with these old illustrations is that they can seem a little antiquated, or extreme. The editorial pieces in particular - showing off the latest fashions from the Riviera, perhaps - have a habit of including silk scarves, matching outfits or fishnet tops. 

Obviously these are intended to catch the eye, and perhaps propose more than one thins at once. And I think it’s for this reason that I often find old photographs more inspiring.

“I spend so many hours going down rabbit holes of old photography,” says Scott. “There’s such a high proportion of really elegant looking people, but going about their everyday business.” 

This refined leisurewear that Scott and I love faded away from the 1960s onwards. The seeds had been sown by the returning GIs after WW2, and the increasing popularity of T-shirts, leather and denim. 

But even in 1966, Slim Aarons photography shows its influence, with actors and designers holidaying in shirts, knits and tailored trousers. 

I particularly the image below, taken in Acapulco, featuring Douglas Fairbanks Junior, Oscar de la Renta and Emilio Pucci. There’s a lot of colour and variation going on, but still - polos, neat shorts, long-sleeved knits. Certainly no vests, T-shirts or logos. 

I feel quite strongly that guys today could get a lot out of these principles of dressing. 

It’s as simple as having some trousers made for you, in a flattering cut, and then finding a well-made polo shirt and blouson to wear over the top. 

Finish it off with some canvas tennis shoes in the summer, suede boots in the winter, and you’re suddenly leagues ahead of everyone else without going near a suit or tie. 

I’m sure it’s an area I’ll mine more over the coming year. But do let me know if you have any particular views on this approach, or specific aspects you’d like me to go into. 

I do like disappearing down a good rabbit hole. 

Related posts in this area are:

Many thanks to Scott for his help, inspiration and images. The Scott Fraser Collection is here

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Everyone allways goes on about how high waisted trousers lengthens the legs… However no one mentions, the reason why most guys nowadays resist it is they shorten the torso and makes your chest look smaller. And that does not look good on many body types without a jacket on…


Maybe it’s because most ready to wear trousers are either super high waisted or quite low waisted. And I’m talking about ready to wear mostly.

Now if you’re built like… well, you, they might look very nice. In fact most super high waisted trousers are modelled for very skinny guys.

However… Just as an example, let’s take 2 guys, both 180cm long. And exactly the same model of trousers. One wears let’s say size 34, one of them size 38… which one do you think will look more appropriate? My guess is the guy that’s wearing size 34.

In my case just as an example, I’ve settled on yeossal size 39 trousers with I’m guessing size 34-35 rise height.. And that’s the beauty of made to measure!


My apologies! No offence was intended! It was the best way I could think of to illustrate why a lot of people are put off by high rise trousers!


What’s not to like from silk scarves eh?


I actually prefer the squarer proportion of higher waisted trousers, since it makes my torso appear larger. I’m fairly slim though, so that is something that can work for slimmer people but not otherwise.
It is the same reason why I want, but don’t, to tuck in t-shirts and polos: I always feel like a long sausage with most brands

Keith Taylor

I find it’s more about balance rather than just, y’know, girth. I’m 5’10 (178cm) and wear a 38” waist, and my transition to a higher waist (spurred on at least partly by this very site a couple of years ago) has been a revelation. I look taller, slimmer and a damn sight better dressed with my pants buttoned closer to my navel than I ever did with them worn at the hips, and I believe the reason is that I have short legs and a relatively long torso.

A higher waistline lengthens my legs, frames my waist around its slimmest point and generally flatters my less than ideal proportions, though someone of the exact same height and with the exact same waist may not get the same benefit if they have longer legs and a shorter torso. As with most things, your mileage may vary 🙂


Hi Simon. Amazing picture of Jean Gabin, one of the finest dresser ever. Behind him is Marcel Carné, director of Les enfants du Paradis, and next to him is Jacques Prévert, poet and screenwriter of this very movie. Don’t know who the other gentleman is, though. They all look great with indeed the gold medal going to J. Gabin.


The other gentleman looks a bit like Georges Brassens. I might be wrong though.


The other one is Alexandre Trauner (bottom right), one of the greatest creators of film sets ever. The picture was taken at La Colombe d’Or, in Saint-Paul de Vence in 1945. Gabin had just returned from the war where he gallantly fought with the free french troops.


Gabin returning from the war, that might explain why he sports a cap, a jacket and a turtleneck while others just wear a polo. He might have been experiencing cold and discomfort not long before this picture was taken. I find that elegance requires being properly dressed for the current wheather, and I was somehow surprised that a gentleman like Gabin was not.


I love the idea and lots of Scott Fraser… I guess for someone like me they are just a tiny bit too out there… Any idea of people making something with a similar style / aesthetic but maybe a tiny tiny bit toned down?

Dr Peter

If we move a bit farther afield from the UK and Europe, we can find other forms of casual wear that are very popular in certain parts of the world. The Cuban/Latin American Guayabera shirt is one example. It is a shirt made of thin, almost voile-like material, often with what Americans call a camp collar. It comes in models with both short and long sleeves. It also has decorative patterns on the front panels. It is always worn outside the trousers, never tucked in.

A second example is a shirt popular in Southeast Asia, especially in Colonial Malaya (where I grew up) and the Philippines. It used to be called the Manila shirt and it resembles the guayabera, but without the decorative patterns. Again, with a camp collar and short sleeves, and made of light cotton. This shirt too is worn outside, never tucked in.

There’s also a whole range of informal shirt styles in India, with or without collars, and often very long (like the Kurta) perhaps too numerous to list. In many of these places, what necessitates these styles is not leisure or sport, but heat! They are more comfortable than classic dress shirts in hot, humid climates. And in a curious reversal, some of them have achieved formality, so that a guayabera can be worn on semi-formal occasions, especially when it would be too hot for a jacket and tie.


Details on the guayabera? I have not seen the style in London before.


Amazing – looking forward to that! I am from Puerto Rico and grew up wearing linen guayaberas sewn at home. The rare times I have seen them since they are sadly slightly garish cotton-poly mixes.

Peter Hall

I do think we have neglected the tailored trousers and we concentrate on tops. I love the soft look.
More on the structure of trousers and how they can define shape would be appreciated ,Simon


This reminds of the time I was in Switzerland and saw someone skiing while wearing a dress shirt with cufflinks, an ascot on the neck and wearing quilted vest on top.

It was a look, that’s for sure.


That particular outfit indeed sounds like a costume, but in general I find skiing (on a sunny day, and not competitively done) is the sport that most allows to wear regular casual-elegant clothes, at least for the upper half of the body. I regularly wear an oxford shirt and a 2ply cashmere sweater underneath the skiing jacket (a technical longsleeve as bottom layer is recommended though). Feels great and looks much better when having drinks at a ski hut.


There’s definitely a balance to be had between fluorescent nylon everything and something a bit more subdued. Personally I have a few merino wool cycling jerseys (usually worn with a base layer) – they’re reasonably warm, close-fitting, stretchy, have pockets on the back, they can be worn for a number of sports (cycling, hiking, cross country skiing, etc.) and they are definitely better looking than most sportswear.


Yup, completely agree. The new generation of high-tech merino garments have massively improved the looks of sportswear. Speaking of which, I am regularly annoying Simon in these comments about what to wear for “real” sports. I usually fall back to Nike and Lacoste for tennis and gym, and Schöffel and Kjus for Skiing, but maybe there are better options (I dont like Iffley Road, to get that one out of the way…). Maybe at some point you find the time to write a piece about this.


Yes, its surprising given that you would assume the market is saturated. Style-wise I have found something I like …if I were a woman: Tory Sport, the sports line from Tory Burch, does a good job.

Ian A

I’d like to find non branded sportswear! Say the innovation of Adidas but without walking round as an unpaid advertising hoarding when I’m doing my sport.


That’s not a rare look in switzerland. On the slopes of St. Moritz I have seen men wearing suit and tie under their Bogner ski suit.

David McQ

Wonderful post, Simon. I do love the longer spearpoint collars on those polos.


Speaking of casual style have you tried Luca Faloni’s cotton chinos?I’m tempted but the cut looks a little too slim for me and I usually like a slim trousers.


I went for their linen drawstring trouser. Slightly regret it for those two reasons. Simon – any suggestions for casual rtw summer / spring trousers?

I find all my tailored linen & cotton trousers can never get the “softness” I am looking for and always look 10% smarter than I want them to…


More of these dreamlike images would not have been a crime, Simon. 🙂


Any recommendations on where to get nice drapey (but not super wide-leg) linen trousers, similar to yours from this post ( but without getting up to Ambrosi price levels? Mostly thinking MTM or cheaper bespoke (maybe Whitcomb & Shaftesbury but I’m not sure it’s really their style?) but I suppose if there are good options RTW, then accepting the need for some alterations, they could work too.


True but Cavour is quite slim


Try Natalino for trousers . High wasted, pleated, lovely drape and great quality for the reasonably low price.


Personally I’d reccomend Scott Fraser Collection, I have four pairs of the classic wide leg trousers and I love them.


One of my favourite photos in the casual chic genre is a rare self portrait of Slim Aarons himself, in front of the Acropolis in 1955. I initially saw it on the Instagram, but I can’t remember where (it may have been Rubato or Adret), and I’m always struck by the simple timelessness of his outfit. You could have worn that at any age in any era in the 65 years since and still looked good. I found a link below although it wasn’t where I originally saw it.

I’d also add Casatlantic to the list of recent brands doing this type of look well!


Surely it’s no coincidence that butt cleavage started its lamentable contribution to the “couldn’t care less” dress aesthetic as low-rise trousers became popular.
Clearing the landscape of such displays is reason enough to see a move back to higher-waisted trousers.

Chris K

Great post Simon, thanks,

A subject I’ve been considering a lot over the past year or so. When I had my first pair of trousers made last year (charcoal cav twill) (and to be honest, I can’t think of more comfortable trousers to wear, and that includes jeans or chinos) I began to ask ‘How can I wear these in a relaxed fashion day to day without looking silly?) In step articles such as this, as well as inspiration from the likes of The Anthology and a number of well dressed gents on Instagram I follow, such as Willy Wang. Something as simple as the anthology’s knitted t-shirt enables someone to tie things together well and even bring something more military inspired into the mix such as a jungle/safari jacket in a refined fit. Great point about summer/winter footwear as well.

One last point and you alluded to it a number of times in this post. The closer to the natural waist line things sit, in my opinion at least, the more natural and attractive things look. I’m now convinced this is why leather jackets for example look better when designers pay particular attention to this detail, as well as trousers (of any sort) being more attractive the closer they sit to the waist. Maybe has as much to do with athletic proportions as anything else.

My best,


This article and the fact that it is no longer below freezing in London has me planning spring summer shopping ha


I agree with Simon’s helpful observation that that smartness can be had from a pair of well-cut trousers and a well-cut polo – I suppose it’s stating the obvious but if an item of clothing looks good, I think 75% of that is just because it fits properly. As for tucking in a polo (or not), for me tucked in is a bit more formal and not tucked in a bit more informal. So, with trousers I prefer to wear tucked in but with shorts, I don’t because I feel that doing so creates a mixture of formality and informality that somehow never really works.

Nigel C

Simon, I really enjoyed reading this – probably because I agree with your sentiments here ! I like the idea of men dressing like adults rather than trying to cling on to the idea of some lost youth through clothing. The guys here all look so comfortable and effortless in their style.
Although it does make me chuckle seeing the fellow in the Slim Aarons photo helping himself to salad with a cigarette hanging from his mouth. It’s not just the clothes that have changed!
Best wishes N


With you Ian. Tucked out is less formal.


I think Rota might also be a good source of well-made casual chic trousers. What do you think, Simon? They are easier to get than some of the British brands over here in the US.


I have quite a few pictures of family and friend gatherings from my grandparents in the 50s, 60s and even 70s (my brother thankfully scanned all the pictures my parents had) and many look similar to the ones here. They were casual affairs, not formal occasions. As a child I remember my grandfather wearing overshirts so frequently that I associated the garment with him (referred to as as shacket), little did I know how common it once was and indeed how popular it would become.

Regarding coverage of “casual chic”, I’d certainly would like to see more. I love classic tailoring: jackets, suits and ties. However, dress is contextual and wearing a suit and tie when everybody is wearing T-shirt’s is not elegant, looks odd and can feel uncomfortable. Yet the wish to be stylish in these casual times and to dress up for the occasion remains. These sort of articles are very helpful Simon, particularly given that smart casual can be tricky to get right.


Great article as always, thank you. I think it’s quite interesting that most of these pictures seem to have been taken in warmer climates. Would be interesting to read your thoughts on a similar aesthetic in colder climates. Also, more input on vintage sportswear and today’s equivalents would be much appreciated!

Peter O

My first reaction to your assertion that the US saw itself as the more practical society is such self-understanding would require contradiction i. e. comparison and
maybe in addition reflection. How many Americans would be able tovcompare – and I guess you must mean comparison with England or with immigrants to America who may have worn clothes from their countries of origin?


What are your thoughts on terry summer shirts? Are they meant to be worn out besides by the pool/beach? Isn’t it extremely “hot” to essentially drape yourself in a towel?


Hi Simon,

Great article and nice pictures. I intend to have trousers made for me and was wondering about your opinion regarding high waisted pleated denim trousers. Is it a little bit too much or too dandy?

Thank you.


Hello Simon, what do you think of Drake’s new silk knitted polos?


Understood, thanks. But what do you think of the concept of a 100% silk polo? Have you had/would you get one?

Michael Maglaras

Simon, this is Michael from Connecticut…one of your best and most thoughtful posts yet. We should all congratulate you on how you keep the “flame” going during these difficult times….Best to you and much success.


This kind of content is so useful. Much as I love my suits, ties and separate jackets, I get very little use out of them since my office dropped its dress code. I certainly don’t use them enough to justify a bespoke commission (maybe a tweed jacket, but I digress). Posts like this that remind us how to be casual, but well dressed reflect what our lives are becoming. Of course the posts on classic menswear are great, but equally the casual boosts like this are well received.


Would love to have a piece on what I would call “polish and artifice”
It is hard, I think, to do casual wear v elegantly without looking too polished (what a less international Englishman might call “Euro”) BUT at the same time carrying yourself without pretension / artifice.

I know you have written about “sprezz” countless times but I always think menswear commentators get in a bit of a tiff about this and overthink it. Just like (no offence intended) your comment over how to tuck in a t-shirt in the right places seems like just overthinking it.

I think this overthinking tends to be seen by others. Maybe not by others in the menswear world (who all tend to overthink) but certainly by “laypeople” who probably don’t have refined taste in clothing but who can (to paraphrase NNT) “smell bullshit a mile away”




Hola Simon soy admirador de ese estilo de vestimenta, que se la ve relajada y muy comoda, actualmente uso shirts negra o azul con un pantalon formal gris, blanco o crema con mocasines negros o alpargatas naturales, tengo 70 años o sea ese estilo es muy cercano a mis gustos, me encanta que publiques estos articulos, buena vida Simon y gracias


The discussion of the high vs low waist in men’s pants is a sophisticated one and appreciated. The near-universal ‘mainstream’ shift from high to low that took place c. 1960, and lamentably yet lingers today, can probably be credited to the popularization of ‘jeans’ where the low waist is the rule. A fallout effect of the tyranny of the low waist is the near impossibility of finding off-the-shelf sweaters, sweatshirts and vests sufficiently ‘short’ not to extend ‘clownishly’ far beyond the natural waist, necessitating the ‘fix’ of folding the hem inward to strike the right proportion. Along these lines, take a look at Jean Gabin in the photo provided. He sports a wonderful ‘knowing’ fix in allowing the lowest few buttons of his overshirt / jacket to remain ‘open’— a strategy not uncommon in the proper wearing of a formal vest. This allows the eye to extend upward to, in effect, the natural waist. This renders the proportion ‘whole’ and balanced, avoiding the ‘clown smock’.
While on the subject of M.Gabin we should note the fabulous ‘drape’ of the cloth in both trousers and jacket, as well as the inspired ‘relocation’ down of the two jacket pockets. This is quite visually provocative and downright Michaelangelesque ‘Mannered’, like two windows improbably but beautifully placed on a building façade!


How would you advise grad students to dress up? Since wearing quality clothes already sets you apart (from students and even the profs) should you stay away from sports jackets, which would make you better dressed than profs? Style and discussion of fashion is already taboo in academia!


Some thoughts as a current grad student: Unless I am presenting a paper or attending a larger conference, I find a sports jacket a bit much. But a nice jumper or cardigan (or overshirt or shirt-jacket in the summer), a tailored trouser, and a well-fitting shirt paired with a suede derby, for instance, don’t look out of place where I work. Anglo-Italian and Drake’s are great for this look, though the latter is sometimes a bit colourful for me.

(Most days, I am somewhere between #2-#4 on the PS “Which office are you?” sliding scale:

I would disagree that fashion is taboo. I know a fair few people who care about fashion and style. I think it’s just a matter of “finding your people”, as so much in academia is.


ZY, i’m glad that you’ve met those people interested in style. I only know one or two who dress admirably but never discuss clothes. I think staff may be more open to talking about fashion, but faculty seem more unconcerned, perhaps to the point of being guarded.

Valerie Steele’s ‘The F-Word’ and the Chronicle article ‘What We Wear In the Underfunded University’ are interesting articles that explore this topic. It’d be fun to hear your thoughts


Do you think an untucked shirt made in casual materials like linen or chambray is good alternative to polo t shirt?


Do you advice going for a tucked in look for cotton polos as well from companies like Gap or Zara which are not actually knitted sweaters?
Do they also look sloppy untucked?


Just one last question regarding this topic, I assure you.
Why do polo t shirts not look sloppy but casual shirts which has the the right length to be worn untucked would look sloppy?

Peter Hall

Would you ever consider a PS casual shirt to address this, Simon? Slightly shorter than the existing short sleeve but in a wider colour range. I really enjoy wearing mine, but would also use a version to untuck.


Still struggling to find good sports wear. Maybe you could do one on that?


Thank you. Exactly, running, playing tennis, rowing, swimming.


60s Knitwear Polos…I can recommend Scott Frazier from UK and especially Connecion Knitwear from Italy