The menswear merger: Sportswear and tailoring

Wednesday, July 28th 2021
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Sportswear brands are adding tailoring to their collections, perhaps as they feel a need to dress up after so many years of sneakers and sweatpants.

Tailoring brands - from the opposite direction - are incorporating more sportswear. This has been happening for a while, admittedly, but it's been accelerated by everyone WFH. 

Some of the brands claim not to follow trends, but this clearly is one. 

Scattered around this article are looks from Aimé Leon Dore, Noah, Drake's, Beige, L'Etiquette, Rowing Blazers and J Crew - and the thing that jumps out at you is that none of them jump out. They all look related. 

Hoodies under tailored coats, sneakers with tailored trousers, blazers thrown over sweatshirts: they've all found pleasing contrast in this mix of high and low.

Compare the Aimé Leon Dore F/W 2020 lookbook to the sportier S/S ‘20 or A/W ‘19 to see the direction. 

It's important to say early on that this is nothing new. 

Mixing sportswear with tailoring was one of the most enduring legacies of Ivy style. The first really innovative designer in menswear - Armani - was fascinated by the combination. Ralph Lauren Polo has done it for years, and it was a big feature of Rugby. You see it every day in high-street brands like Jack Wills.

But that doesn't stop it from being a trend today - and it's a significant one when so many brands that are seen as being new and exciting in menswear are working it. 

I don’t wear the look as much as friends I know, so I asked them for their views first before reaching my own. (Always good to start open-minded, in art as in life.)

Jamie Ferguson reflected on why the mix-up has been so popular: “There’s been blending of styles before, but I think these are probably the two most extreme points - as in opposite to one another - that your average guy on the street can still look at and think 'yeah I can wear that'. It's not too off putting.”

Jeremy Kirkland and John Reuter at the podcast Blamo! have been chatting about this for a while. John reflects: “So many menswear and street brands are becoming remarkably similar - so much so that at times all their images and styling could be part of the same lookbook. 

And here's the thing: I'm totally here for it. I love the mixes of classic clothes that feel new and like they've always been around. They remind me of the tailoring/sportswear mixes you could find a young Alan Flusser in (subtler than the bolder cross-genre mixes he enjoys today). 

“Folks are dressing down tailoring and dressing up streetwear, and whichever direction they come from it gives them new brands to choose from.”

Jamie adds a practical point I hadn't considered: “The veering away from the slim look that dominated the early and mid 00's means that bulkier sportswear items like rugby shirts, hoodies etc can now be worn under a raglan sleeve coat or blazer. There's room for it all.”

I’m a little conflicted as to whether this is a good thing. On the one hand I love the fact that younger streetwear brands are embracing tailoring, and telling a new generation about the pleasures of a tweed jacket or a camelhair coat. 

But I also think it’s a shame that Drake’s isn’t putting out the same style as it was 10 years ago, because I loved that style. It was more about how old-English style could be creative and contemporary, rather than how it combined with streetwear. 

This is, inevitably, very personal. My style is more understated, with only single items of sportswear used for high/low contrast, and then only occasionally. Examples include the hoodie with a PS trench coat, and a baseball cap with a tweed jacket (both below). 

For how I dress, this is simply using sportswear in the same way I’d work in items from other traditions, such as a Western shirt under a tailored jacket, or a military parka instead of a coat.

I do love mixing sportswear and tailoring in whole looks, but with more refined and vintage-inspired clothing. This is the ‘casual chic’ that I’ve written about a few times in the past year, and which I continue to be obsessed. 

For me, there’s particular pleasure in the artful use of a polo under a crewneck sweater, instead of the more standard shirt. Or a slim, well-made deck shoe and full-bodied knit with tailored trousers. 

There are images of these below, featuring Saman Amel and Stoffa. These, along with Rubato and Adret, are the brands that embody this lower-contrast merging of tailoring and sportswear that I like. 

Still, I think it says something about my attitude to clothing that I still find these images of Aimé Leon Dore, Drake’s and Noah both beautiful and inspiring. If you’re actually interested in clothes, I don't think your interest can ever be limited to just things you would wear yourself.

Plus, this open-mindedness can lead to unexpected inspiration. For example, the image below from Drake’s makes me think my grey Loopwheeler hoodie would look nice under my Anthology polo coat, even though I’d never wear matching sweatpants. 

The second - easy, chatty, great-feeling - shot from Aimé Leon Dore makes me want to try white jeans with grey knitwear and beige outwear. Plus a cap. I’d wear Alden LHS loafers, but it would have a similar feel. 

And the third, perhaps the most unlikely, makes me think how great grey trousers would be in a wool that was much hardier than flannel. I wouldn’t wear it with a vest of course, but with a T-shirt or knitted polo, maybe. 

I’ve said it so many times before, but people seem to forget just as often: you don’t have to copy whole looks, or even any individual pieces. Just take it all in. Inspiration can come from anywhere. 

One thing that should be noted about these high/low combinations is that they are inherently risky. 

They are instinctively attractive, and the pay-off can be big if you’re after a high-impact look. But it's also easy to get them wrong: either forgetting that you don’t look like the model in the picture, or that your clothes are slightly (but significantly) different. 

I think this is particularly true of looks where everything is very loose and slouchy - the jacket hanging off, the trousers puddled on the top of shoes. It takes both awareness and attitude to pull that off. 

But none of that stops me finding these images inspiring. There’s simply nothing more stimulating than someone with both taste and talent bringing their perspective to something you love.  

Plus, it’s been easy to feel in recent years that tailoring has been slipping off the radar. It’s great to see people like Aimé Leon Dore bringing it back. 

The images are taken from the following lookbooks. Do shout if there are any others you'd recommend:

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Hi Simon, you are absolutely correct in saying that it is not necessary to copy whole looks. Colour combinations one hasn’t previously tried can emerge from viewing the new trends. However (and I realize this is subjective and deliberately provocative) some of these looks, despite the beautiful photographs, seem to me to be not much more than a rag-bag of old stuff bought in charity shops.


Although there is nothing that I particularly like or dislike about this look, I do think it is really more suitable for a younger man. It’s also a little sad, if as you suggest, there is a creeping homogeneity about these brands, as they each started out with a particular noticeable ‘take’ on menswear that differentiated them from each other.


I’d disagree on the age point. Well I would – as I’m in my sixties!
I’d suggest people go with looks that they feel comfortable in wearing. I have seen many examples of men and more so women carrying off these type looks (my wife being one), the picture with the bike is a good example.
To suggest otherwise is I think at best patronising and at worst?
And to bear in mind the spending power of the older generation.
The Grey Fox blog is a great ambassador for the senior generations interest in fashion of all types.
Apologies if I sound emotive, it’s just that I think we wouldn’t pick out any other demographic.


Thats fine Stephen, but I am also in my 60’s so it isn’t a dig at older men, its just my take. Personally I wouldn’t certain things.


No worries Darryl, fair point.


It’s a good point, you should wear clothes you are conformable with. I don’t think the ability to carry off any look is entirely dependent on age. 
On the other side of the coin, I’m in my early 20s, a recent grad; I’ve occasionally worn a university hoodie over a button-down on Casual Friday (wearing college-wear is quite common here). But, personally I find the ‘looks’ here a little forced.
Clothing is social, every ‘look’ has connotations. Some good, others less flattering, which may differ depending on context/person. Clearly, the style leans on the public school/NE-prep cache – it’s collegiate, athletic, privileged (maybe aspirational?) – and by extension youthful. The heady stuff that RL dreams are made of!
Ofc, there’s a difference between youthfulness, and being young. Certainly age is a dimension, but (given the athleticism) so too is build, lifestyle (being sporty) and personality (being playful) etc.


I’m with you George, these looks come off as really contrived to me. I’d have to hold myself back from laughing if I saw someone wearing suede loafers with tracksuit pants IRL. Or an overcoat with a tracksuit.


I would also add that Anglo-Italian are very good at producing items that tree the sporty/tailored line. On hardy grey trousers any material in particular you are thinking of?


Such a look was very popular in Berlin in the early 2010s. Menswear brands, as always, are a bit behind in such trends – but I think that’s a good thing.
For the success of the look described I think comfort (without losing too much attractiveness) is an essential element. Stòffa’s peach cotton is a good example. Feels like sweatpants, but looks good dressed.

Peter Hall

The apparel of the classic British sports – cricket, rugby, polo, rowing, go so well with this look. Since the 70s, I’ve mixed rugby shirts, cricket jumpers and tennis wear into my normal day wear. I think it works best in spring and autumn.
I totally agree it is all in danger of merging into one amorphous blob.
It is a great combination to use with grey(as you mention), the grey sweater and white OCBD is an enduring look. I find wool coats with a textured weave work really well. Personally, a coat, rather than tailored jacket – the coarseness contrasts nicely with what can be a sleek look.
Finally, a plug for Patrick Grant’s community clothing make excellent rugby shirts(and are uk made). They are perfect for kid duties and have all the nostalgia of school days.


Thanks for the thought provoking article Simon, I like your point about being able to appreciate style choices that look good on others that you might not wear yourself, it’s a wise way of thinking rather than straight away having prejudice about someone’s appearance, and thereby having an acceptance of others. Slightly similar concept for the world of horology (a primary interest of mine!) I read a couple of years back on HODINKEE : the writer commenting that reviewing a watch and appreciating it doesn’t have to be about him/her wanting that piece themselves, but instead looking at it objectively as how it fits in with all watch enthusiasts..therefore being comfortable with not writing it off as “something I’d never wear”. Lots of great articles recently on PS too ?


Interesting to note that the sportswear in question tends to be from a few specific and, let’s not mince words, broadly exclusive sports – rugby, polo, racquet sports, track & field. These images remind me of school blazers over games kit on the bus home after training sessions. It’s a public school look at heart


Exactly my thoughts. The pictures in this post all look like a ca. 2010 Jack Wills look book exactly because Jack Wills at the time tried to imitate the look of upper middle class students carelessly combining whatever they found in a wardrobe that consisted of “good” clothes and sportswear. And of course that is indeed an attractive, somewhat sexy look – close to the original Ivy spirit and equally aspirational. Even in Simon’s own photos of course it has to be a Berkeley cap, and not something generic from Nike. But I think aspirational clothes easily look a little tacky/sad on older people (i.e., after university), so the look is better left to young adults.


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Hi Simon,
Great article. Being inspired rather than slavishly copying is for me the way to go. That’s one of the reasons I read permanent style.
I think your take on the example around the combination of hoodie and polo coat is spot on, for me jeans not sweatpants, but wouldn’t have thought of it at all before.
On a practical point for layering, some technical clothing (eg running hoodies) will provide the effect without excessive bulk. I’ve done this under a padded parka.
Would be interested in something on winter parkas at some point, any plans?
Btw looking forward to the Drakes Polo Coat. I really like the Anthology / Permanent Style collaboration, but was reticent to order with all the inherent duties, fees and the like!

Thanks again for all the interest you create.


Some cashmere hoodies would possibly work in the same way too.


Maybe it’s because these images are all from look-books, but I find the attempted ‘casualness’ very silly and affected here. It feels as if something which would have happened naturally and organically – putting a tailored jacket over sportswear, slipping on trainers with suit trousers – has been teased apart and micro-analysed to the point where it is now only a simulacrum. Studied nonchalance is no nonchalance at all, surely?
(TLDR: It’s all Ralph’s fault, innit?)

Jack Williams

One of your most provocative posts. Excellent. The richness of art has always come from the appropriation of vernacular traditions. Look at Mozart’s operas – from opera buffa, at Duchamp and Piccaso’s “found objects, at the influence of jazz on contemporary music, and so many more examples. What you call low to high in men’s clothing follows in the same trajectory. We should welcome this infusion of ideas, both those that work and those that miss. Here in New England with our frigid winters, mountaineering and winter sports apparel has become the norm for “high” dressing with down parkers and wool beanies over suits in the city. My “go to” coat in January is a Kanuk “patrouilleur” with its high collar worn over a tweed suit. And nobody gives it a second look.


A very interesting read, Simon. But you’re right, nothing new and very American. Would you say that this will impact the way in which the more formal elements of these outfits will be worn even without the sportswear? As in looser, more accomodating fits in tailoring? Or is that something that you feel is already in motion with a brand such as Drake’s? What about brands such as Trunk Clothiers and Boglioli and such like who are all still very ‘slim fit’, is there still a customer for that look?


I spent the last few months deformalizing my suits and sportjackets. Less buttons on sleeves, less flaps, even jogging stripes on a few lightweight suits. They actually get me excited about tailoring again which I though was getting boring and totally out of place in recent years.

HK European

I can find my personal style reflected in the spirit of this post. I increasingly take a high-low approach to dressing, both styling-wise and literally. So if if I wear nice tailored trousers I’d wear a top that is more casual, perhaps a chore jacket or a cropped jacket like an armoury three-point blouse. Similarly, if I wear a sport coat I’d pair it with a 5-pocket trousers or a nice japanese raw denim. Almost never a classic tailored trouser and blazer combination. When the top or bottom is tailored, the other side (or height) of the outfit balances it in being more casual. It just feels more natural, more modern somehow.

Tommy Mack

Simon, have you seen the French thriller series Lupin (on Netflix in the UK)? Omar Sy’s titular character has a great tailoring/sportswear wardrobe which is both dapper and playful. His aubergine Fred Perry track jacket under a navy peacoat was a personal favourite of mine. Actually, as you’d expect of a series set in Paris, everyone is very well-dressed in Lupin. Hervé Pierre’s slouchy old-money tailoring is particularly great!

Tommy Mack

It’s great fun, knowingly silly but gripping with it and beautifully filmed.


At least there’s more variation in this than every menswear enthusiast on Instagram wearing neckerchiefs because it’s the summer trend and post-covid malaise has cost everyone some imagination.


Well balanced and thoughtful article as always – thanks Simon.

I agree entirely about the perceived homogeneity of this look across all brands – it’s a look I may dabble with but not go for wholeheartedly. The colour combinations do give inspiration.

I miss Drake’s from a decade ago as well! I find the price to value ratio (for me) harder to justify, especially with the growth of the sportswear elements of their range. I guess there is a bigger machine to feed these days.


Every now and again I make a foray into sportswear but never make it stick. I have, what I think, is a great grey hoodie. Some aspect of tailoring to it as well. The moment I wear it children, friends, anyone I know comes at me saying “it looks good but it’s not you”. Am I defined by my clothes or do my clothes define me?

Rob Grant

Hi Simon
I’m on the side of the ‘oldies’ too. I’m in my 70s and since retirement have a basic hi-lo uniform which I find supremely comfortable for everything from dog-walking to shopping to lunches.
I’m ‘Hi’ from the waist up and ‘lo’ from the waist down.
Obviously it’s winter in Australia so I wear one of a few navy or camel cashmere single breasted notch lapel overcoats, or a cashmere pea coat over a cashmere crew neck sweater (no shirt). Maybe a cashmere scarf.
I find cashmere flexible, soft, light but warm in winter but not too much so. Everything is either navy or grey or camel for one coat.
Below there are either jeans or cavalry twill trousers in navy, white, ecru, grey.
Then I wear sneakers, white or solid suede in navy and brown. They are mainly from Norman Walsh or Bexley.
So it’s all comfy and understated and despite my great age, never draws a second look.
I haven’t worn a sport coat or shirt for years – far too restrictive compared with the above combination, for me at least.
I will change in summer, though to lightweight chinos (Vineyard Vines) and a bunch of beautiful pure linen shirts, some for wearing untucked with the sleeves rolled up and made up for me by Proper Cloth in NYC, who are very reliable.
Oddly, I take some inspiration from women’s wear. Camel overcoat, jeans and white sneakers can look so good. Casual but never cheap.

michael Ryan

I remember dressing very casually in the 80s in London but wearing the latest in cool jackets from Top Man – a tweed sports coat. Definitely not mixing it as well as any of the models in the photos here but one of my first attempts at dressing well.


I’m so glad you’ve noticed the same trend with Drake’s. Ten years ago I used to love the shop; in the last couple of years I’ve only found one thing I feel I can actually wear.

I know that’s not quite what you meant, but I just don’t really want to dress like a teenager.


Interesting discussion, especially because it reflects the era we are living in.
But let’s not overstate the style:a tracksuit is still just a tracksuit, irrespective of the expensive label and the svelte model.


I am so disappointed with Drakes. I used to love them as a brand. It feels like they are trying so hard and still attempting to figure out their identity. They had a great formula and focus, and they have steered away too much. They do not need to be an “everything” brand. I fear that they will no longer be around in the near future. And their prices are just offensive these days. Nowhere near worth the quality. I hope Michael and Mark are reading these comments.


I couldn’t agree more. Well said!
The same could also be said about other brands such as New & Lingwood and Hackett that have lost their way.


I’m also a bit dissapointed in Hackett. 4 years ago picked up chinos in tk maxx for 30£, felt actually expensive. This spring picked up same chinos another pair, this time directly from Hackett and seems quality has gone down. Material is thinner and overall trousers just feel cheap…


So very true. Remember seeing their winter lookbook from a couple of years ago, the Oxford one and being in total awe of absolutely every item in it. Forward wind a couple of years and they look totally devoid of anything original at all. Garish colours and cheap looking products that would not look out of place at Next. And don’t start me on their obscene pricing of late, fast becoming a bit of a joke. A real, real shame. They appear to have totally lost their way.


Can you elaborate? Very interested. I like them but haven’t been aware of them for that long. However, I’d go as far as to say I’ve noticed a shift in what they’re putting out there in the last 2 years.


+1 deeply disappointed with Drakes. I came to them attracted by their foundational items, ties and squares. After years of finding increasingly difficult to add ties worth wearing to my collection they were a revelation. Not only the quality and variety, but also how attractively they were displayed on their website. Look at them now. Not only the designs have plummeted, but their photography is appalling. Dull, soulless, looking no better than in a department store’s pitiful web.
I guess they keep them half heartedly in case some sales come from their past reputation, but these days I am definitely more attracted to Shibumi and HN White, who convey a feeling of proudly keeping faith in the item.


One person you missed, who’s been mixing high and low for a while is Jerry Lorenzo of Fear of God, and now Zegna and Adidas. His designs also channel Armani’s cuts and colors.

Adrian Hackman


I am going to embark on a career in advertising. People wear black and grey; gymwear mostly. I am thinking of mearging tailoring into the mix. The problem is to find ready-to-wear clothing: brown are more common and therefore brown buttons on shirts etc. I also often find myself in political disscusstions about gender when I wear traditional menswear; something I abhor. I try to avoid identity politics; I would be thankful for any advise.


Yes, that’s precisely what I need! I have bought one black and one grey overshirt from Laboureur now and I think that is preatty gender neutral workwear. I am considering wearing a grey herringbone tweed sport jacket sometimes— maybe sneak in some tailoring and slightly smater black dress shoes? I think crewneck sweaters from William Lockie (from a store here in Stockholm simply called Tweed) are next on my shopping list. I am really fond of traditional menswear and I think the point of gender neutral clothes seems to be about massproduction and utalitariansim.


These looks: hoodies and sport coat, sweatpants and loafers etc. have all been around for some time. What has changed is the view on when and in which situation or context they are considered appropriate.
I think most clothes can look god provided that they drape (hang) well and does not work too much against the ideal silhouette. Even though I truly despise sweatpants, I actually think they can look a lot better than a pair of slightly too tight trousers. I suppose what I really don’t like is non vertical creases, especially around the crotch area. But for some reason I still love linen 😉


Can’t believe I missed this article! Personally I was all about streetwear and sneakers during high school and college and I had to change my wardrobe towards classic menswear when I joined the corporate world. But with the pandemic I got used with working at home and I don’t think I’ll see office time anytime soon. So a big part of my wardrobe became sort of irrelevant. I can’t wear even the most casual tailoring when I’m with my friends because I would always be overdressed. So this trend has caught my eye and it got me thinking I could incorporate some stuff in my day to day outfits. I don’t know why I’m looking for some sort of approval so it’s nice to read an article about this theme on PS.