Be open minded. Or, what is style?

Friday, September 3rd 2021
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I believe that core to understanding clothes, and perhaps even to enjoying them, is appreciating styles that are not your own. 

If you can’t, it closes you off to dozens of ideas - something as simple as the shape of a sleeve, or a colour combination - that you’d like in another setting. 

And even if it never influences you at all, it’s a healthy challenge. It refreshes and reinforces your own ideas by reminding you what you particularly like about your clothes. 

If John Stuart Mill had had an opinion on clothes, it would surely have been this. Openness to ideas both avoids any chance you might be wrong and - if you refute them - helps you understand your own opinions better. It avoids stagnation. 

And you thought PS took itself too seriously. 

Let’s take an example. In a recent post, a reader criticised chore coats and similarly straight-cut, shapeless clothing. 

He argued that being flattering - by implication, shaped to the wearer - was by far the most important aspect of clothing. Without that, it was hard to see how clothes could have style at all. 

Generally, I agree. Fit is the attribute of style most commonly underrated, and I make that point frequently. But that doesn’t mean less fitted clothes can’t be stylish. 

Clothes can be loose, baggy, floppy and still have great style. You see that in a lot of the recently rekindled skater and 1990s looks, and in tailoring too. Armani did it wonderfully, as we’ve covered, and someone like Michael Jordan was known for it. 

Famously, Jordan’s style came about because Chicago-tailor Burdi put a suit on him that was much too big. Jordan loved it. He was a big man, and always felt suits were too short for him. 

I would never dress like that. But in the example below I think he looks great. He looks natural, elegant - and gets away with the two-tone shoes and T-shirt because of who he is. 

There are even things I would take from the look, such as the green cast of that grey suit, and how well it works with black. 

It’s important to emphasise that we’re not slipping into relativism. 

Just because many styles can look good, it doesn’t mean everyone looks good. It’s possible to dress badly in any style - and indeed, dressing well in another style is likely this thing we are recognising and appreciating in others. 

The guy on Jordan’s right looks very ordinary compared to him. His shirt is too strong a blue; the trousers are too low. (Not low rise, but lower than they are designed to be. The fork is dropped way below the crotch.)

The reason he doesn’t look great is not because his style is different. He just hasn’t executed it effectively.

So what constitutes this act of dressing well? What makes someone stylish? What do Michael Jordan and the Duke of Windsor have in common?

I don’t pretend to know the answer, but there are a few things that I’m pretty sure contribute. 

One is looking natural. Not forced, not awkward, not stuffy. You are comfortable in your clothes and know what works for you. Another word might be authentic. 

Two is consistency, cohesiveness. There is clearly consideration at work in the whole. Even if you’ve worn that outfit a hundred times, it was thoughtful at the start and still looks it. 

A third, related to this, is traditions and education. It doesn’t matter whether people obey the ‘rules’ or not - the point is that they’re aware of them. 

(And for those that say many people dress well without knowing the traditions - it’s not true. It’s just subconscious. Some have absorbed rather than learnt, and while they wouldn’t state a rule, they would say the same things ‘just look wrong’.)

A fourth is personality. The best dressers are elevated from the norm by expressing something, having a view. It might come across in colours or in little accessories, in something loud or quiet. But they don’t look like a carbon copy of somebody else.

There are certainly other elements, and there is a lot to pleasantly argue about in each one. I look forward to doing so in the comments. 

Many people do not dress like me, yet I find them inspiring. 

Tony Sylvester (above), bless his Grecian slippers, wears many things I never would. But I’m always interested in what he’s going to try and work into an outfit next. 

The beret may never become part of my regular clothing, but it’s still interesting when he talks about the 'flight' of different styles. And it makes me reflect on proportion in other hats.

Why is leopard print so much sexier than, for example, tiger? Why do turned-up brims suit some heads and not others? Do band collars look best on bigger men? All questions Tony has made me ponder, while looking at outfits I wouldn't wear. 

Be like John Stuart Mill and let all the crazy ideas in. It’s the only way to avoid - in his phrase - your ideas becoming ‘dead dogma’. 

The people that don’t are the ones you're familiar with from forums. The ones that insist, loudly, on the rules and concoct their own definition of a gentleman. They tend to be noisy, condescending and oddly indignant. 

Sometimes those proclamations can sound like confidence. I think it sounds more like fear. 

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Nice one, Simon. I like these ‘thought pieces’ a lot. And my commiserations to poor Ray Allen, who, for the record, became far more stylish later in his career. By the time the 2005 NBA dress code was instated, he had learnt how to dress.

Michael Murray

I love that Luke pointed this out! I was chuckling when I saw the picture as Ray became a very sharp dresser as his career progressed.


Go on Luke, mention the player who led to David Stern bringing in the dress code…


Thanks Simon. Confidence is paramount indeed, but physiques as well. Some guys can just pull off anything. Not only because of their personality, but because their features would make them look good even in speedos and flip flops. A young Michael Jordan being the perfect example of this. 


The points raised here are very true and important ones. I often find the #menswear scene incredibly stagnant and unimaginative, epitomised by the Northern European, lawyer/ financier menswear instagram account which churns out endless images of midmarket tailoring in soulless combinations. There’s nothing i find more off putting.
Whilst i applaud the sentiments in this article Simon i cant help but feel that this site may have gone a long way in encouraging the opposite to the points raised here whereby a dressing by numbers/ overly analytical approach is taken to the detriment of allowing any character and or ‘rule breaking’ to come to the fore.
Please take this comment as a point for discussion rather than a criticism.


Interesting you mention ‘different voices’ appearing. Have you noticed a change in reader contributions? I wounder what differance you are reffering to?


I think we readers need to keep J’s point in mind, but I think Simon that your reply is right. Your approach is helpful for men wanting to learn what they are doing relatively quickly.
And it is important to learn how to walk before you try to run. For example, you are much more likely to develop an interesting personal style that makes you look good if you know what a well-fitting garment look like, or what types of shoes and trousers are generally regarded as “consistent” (e.g. in terms of formality) with particular types of jacket or knitwear. It’s partly a question of getting some basic knowledge of the tradition, and partly a question of developing the ability to notice and see things – and that is essential whether your personal style is going to end up being quite conservative or quite eccentric.


I am reading this topic with acute interest. I consider myself to be in possession of a personal style of dressing that I have developed since I was a teen. I like putting on a suit and tie very much. I once wished that I could wear a suit everyday like some of the men in my neighborhood( they were not lawyers or bankers by a long shot). By reading men’s magazines like GQ and Esquire I was exposed to a wider world of men’s fashion. Because I couldn’t afford most of the clothes shown I looked for something close to it but affordable. It worked because I was named best dressed senior the year I graduated from High School. By doing a lot of improvisation utilizing clothes that I bought working summer jobs and combining them with suits from my grandfather that had been tailor made for him by my uncles in the military who were stationed in Europe and the far East, I began to acquire a sense of style that has stayed with me over 50 years. I take in the advice and criticism that are made by you Simon and others with the caveat being I have free will to use or discard the information. I do care what being people see or talk about dress, but I do not want to be bored with anything in my life. I have been a musician playing r&b, jazz, Afro-beat, South African town ship music, Reggae, Funk, Salsa and what ever else pays the rent. These wonderful musical styles have influenced me musically as well as fashion wise. All in all I have had a ball dressing the way I like and I reiterate not being bored.


To defend the PS-site in its own words (how cheap): my impression as a reader has been rather that PS is just providing “the tools” and you have to decide for yourself how to use them or whether you want to use them at all. Maybe use just some of the provided tools, which is what I like to think I do. (
But either way it remains true for me that the views expressed on this site (PS and reader’s comments alike) are a constant supply of ideas and views that are (until that time) not my own, which I find stimulating and entertaining. I could not stand a site/forum where people constantly talk about things I already know and I totally agree with. How redundant and annoying would that be?


Interesting. I have come to the conclusion that I look bad in everything. There is no combination of clothes that works for me, just varying degrees of unsuitability. After years of reading PS, I haven’t quite worked out why this is, though I have discounted a few theories. My father is the opposite. He looks good in absolutely everything, and he spends the absolute minimum on clothes and just throws on whatever is to hand.. I met him recently and he was wearing paint spattered red trousers and ill-fitting old polo shirt, and a cheap, and battered old hat – I was in my expensive and carefully curated A & S and RL purple label finery. He looked great. I didn’t. What a mystery it all is. But thanks Simon for giving me plenty to think about over the years.


I wonder why that is, Phil (presuming you’re right about it and are not in fact very stylish but not aware of it). One answer might be in your phrase ‘carefully curated’, which I think links to Simon’s point in the article about looking natural rather than forced. I have also known men who look good in anything, regardless of cost or whether they care much about clothes, as well as men who rigorously follow all the ‘rules’, spend a lot of money on high-quality clothes, but still look like they’re wearing a costume – like they’re trying too hard, and trying to be someone else. Sometimes men with no sense of style think if they spend enough money they will obtain it, but it doesn’t work like that.
My advice would be not to be as careful and try to think what it is you like in clothes, and what suits your body and your personality. Too much effort shows, and looks stuffy. When director Terence Young was given the task in 1961 of making an unknown and rough-hewn actor called Sean Connery into the stylish secret agent Sean Connery, he famously sent Connery to Anthony Sinclair to have a suit made and then told him to sleep in the suit until he felt comfortable in it. It was a pretty good tip! I wouldn’t suggest you wear your A&S suits to bed, but perhaps treat them a little more callously, not in terms of making sure they are clean and so on, but in terms of your attitude towards them. They’re top quality – now forget about it and wear them how you want. Take off the tie. Wear the trousers with a chunky sweater and some combat boots. Whatever you feel like. But if you can live in the clothes, rather than have them wear you. I suspect that is the lesson your father has learned instinctively.


Thank you both. Good advice. But perhaps I was exaggerating a bit. I don’t wear high end clothes all the time, or have limitless faith in ‘quality’. And I do enjoy clothes and find the subject of style fascinating. As to my Dad, when I say he ‘throws’ things on, he does, but I suspect with an innate skill that operates at a subconscious level – and which you either have or you don’t. I also think personality is a big factor – I’m a big believer in the idea of ‘carrying off’ clothes, which correlates with demeanour and attitude. Again, not something you can acquire.
Build and pallor are also important, I think. My dad is chunky and has a ruddy complexion and I find men like that (Ethan Newton? Bruce Boyer?) have a bit of an advantage. I’m skinny and pale and people often ask after my health (though I’m actually in pretty good nick).
Perhaps that’s problem. An article there perhaps Simon? How to look stylish when you look a bit sickly? Only Sid Vicious (arguably) ever pulled that off – but I don’t think I want to go down that road at my age!


This is an interesting comment. I think your probably being hard on yourself. I dont believe that there is anyone who cant find a combination that works for them its just a case of finding the right one. In this case it sounds like approaching it from a different angle would be best. When i get in a rut with style i sometimes try one of the following;
Think about what outfit i wear whereby i feel totally at ease and dont think of what it is that i am wearing. This may be the old chinos, shirt and boots i wear for DIY or some form of clothing that is worn for a specific activity rather than for the sake of style. This will bring with it a sense of style purely through the ease with which you wear it. Start from this point and then maybe add a nice watch, a finer pair of shoes or a scarf and off you go. Dont try to hard.
Secondly would be to focus on something in your life you enjoy that isnt clothes. Alongside clothing i paint and draw allot as well as garden. If i feel i am excelling at anyone of these pass times on any given day then i feel more confident in myself and therefor stylish in what i may be wearing. Although these may be personal, internal feelings it can be outwardly noticeable. Sat in the pub in my creased gardening clothing with muddy knees i’ve never felt so stylish.
Another point is to ask your significant other what he/ she thinks you look nicest in. For me this is a white crew neck t-shirt rather than tailoring. I have recently started to exercise several times a week [swimming] and i am currently in the best shape i have been in for years. All of a sudden just wearing a white t shirt looks and feels great.
I hate to say it but you wearing a several thousand pound A&S/ RLPL is not neccessarily conducive to looking good. Infact i would say you are less likely to look stylish in that than if you focus more on the non clothing elements of style.
Finally, try putting an embargo on buying any new clothes for a year. Hard i know but this will force you to work with what youve got and allow some of the clothes to age and wear in which is also essential to looking good. High/ low, old/new all should be included in an outfit not just the new and expensive.


Again, thank you both. Good point about Fred Astaire and Gene Kelly Simon, and some helpful tips J.
I think I am more disadvantaged by my ghostly pallor and permanently exhausted look (which people kindly point out to me several times a day!) than my slim figure. I am actually in reasonable shape, as a regular exercise regime is the only positive thing that came out of lockdown for me.
As for skin tone, sadly, like many Scots, I don’t tan, I bleach – that’s mother’s influence there. On the positive side, I still have a full head of hair unlike Dad – it’s swings and roundabouts with the gene pool.
Anyway, I’ll leave it there before this turns into a personal therapy session. Thanks again.


Hi Phil, Perhaps you are overthinking your style a bit. Whilst you should generally look after your clothes in my experience ‘wearing them in’ does tend to make me feel less self conscious. It took me a while to just get used to a blazer again as we emerged socially from lockdown.
On your point re shape. I spend a lot of time in my advanced years trying to maintain a slim physique and am of the opinion it’s easier to dress a slimmer frame. As I once read, a healthy vanity can help to maintain a healthy heart! That’s said any build should not be an impediment to dressing stylishly. The Tony Sylvester link is a great example.
Finally you probably look a lot more stylish than you realise.


I think another way of describing this issue would be to think of the ‘art and science’ of menswear. A combination of rules, settings, temporal moments, custom and practice etc spliced with a painters or musicians sense of the inexplicable and magical.


Hello Simon, really interesting points. Of your four “pillars” of being stylish, I would argue your points 1 (being comfortable in your clothes – let’s say wearing with them confidence), and 4 (personality) are the key traits.
Using your example of Michael Jordan, I couldn’t also help but thinking when watching The Last Dance, how good he looked despite the clothes not being remotely my style. The suits were clearly “of their time”, but he obviously wears them like they were made for him exactly how he wanted them (which you have confirmed they were) with complete confidence, and they shout Big, Bold, & Brash – which matched his persona to a tee.
Run that ruler over anyone else you find dresses with style and I reckon that formula works.


If the next article isn’t “How to dress like J.S Mill”, I’m sure I and many other PS readers will be very disappointed. You could do a mini series taking in Locke, Bentham, Hobbes…

Maggie May

David Hume could out-costume
Wilhelm Freidrich Hegel (etc, etc)


There is no way Hume is out-costuming anyone…


Great article!
First thing that came to mind is armani_do on instagram. He has many things that I wouldn’t wear yet I would say it’s one of the most inspiring accounts I follow. 
I don’t really agree with this idea of people “getting away” with a certain look because of who they are. In this photo of Jordan I don’t think the shoes look bad with the whole outfit, but for example, I find Agnelli wearing the watches on top of the shirt cuff just as tacky as any John Doe doing it, yet more than once I’ve heard this idea that “it’s ok if you are Agnelli”.


Hi Simon,

Sorry to be a dissenting voice here but I dont think Jordan looks in any way elegant. He looks rather slouchy and careless, like someone who borrowed a suit a few sizes too big and didnt bother looking in the kirror, or did but didnt care. It is possible to look elegant in relaxed “unflattering” fits without looking too composed. Tony Sylvester here is a good example, as is Ethan Wong and Ethan Newton, but I wont put Jordan in the same category. (Although perhaps I’m being unfair comparing an athlete to menswear industry people)

Further, I think that your series on the “Rules and how to break them” is on point when it comes to open mindedness.


Not really Simon, no. When Tony, Ethan, and Ethan dress “relaxed” it’s like the’re saying “I’m relaxed, I’m comfortable, I’m not trying too hard but I’m still stylish because I care…it’s not mainstream but its still good” whereas Jordan looks he doesn’t care at all.

It’s the difference between someone who unbuttons a double breasted in the name of “Sprezzatura” (forgive me, I know you have a lot of thoughts on using that word) and someone who does the same just because he’s slouchy.


Thanks Simon. I’m always glad PS remains a free marketplace of ideas.


but what if that that ‘carefree’, laid back look is exactly what MJ’s style is?
there is definitely some thought in his outfit. look at the trouser break for example, i think we all know what a ‘cant be bothered’ trouser break looks like.

Peter Hall

I think the biggest danger ,for me, was not looking natural. I’m definitely a jeans and shirt guy with a sport jacket/or knitwear. I always return to this combo because I’m confident knowing I have good fitting jeans, jackets and shirts.
PS gives me great advice re colour and texture(discovering that green, for instance, really suits my colouring) and appreciate inspiring pieces such as this and seeing what other men wear.


I think the key here is to understand style, once you are intelligent about it you can be a rebel otherwise if you haven’t bothered learning and trying to be unique I’m afraid you simply look silly. It’s reinforcing what we are trying to achieve as a men’s fashion community, share the knowledge about quality and stylish menswear. Once you understand the basics and know how to look stylish in a modern sense you can experiment and find your own way which is unique and compliments you as a persona.


Thanks Simon. A useful article for the current times. It feels like we are in a transition period for menswear. COVID is coming to a close but there’s no sign of men returning to wearing shirts, ties and jackets. My feeling is that elegant dressing has become divorced from occasion. Wearing navy to the office, business casual on Friday has become irrelevant. We’ll all have to learn to dress in ways that reflect our individual personalities in an elegant way. It’s liberating but it’s certainly not easy. This kind of article helps readers to frame their thinking without giving prescriptive answers.

David Flores

For more than a century dressing has going down the hill according to the current generation. I wonder if in three or four future generations will see us as an example of elegance wearing kakis.


Simon, Interesting article. I do find the diverse range of subjects very welcome. One small gripe is a wider tendency among many fashion writers to make an icon out of the Duke of Windsor. He had every advantage, concocted a contrived style ( in my opinion) and his behaviours at best left a lot to be desired. I would suggest reading ‘Kings Counsellor: Abdication and War: The diaries of Sir Alan Lascelles. Far better examples would include George VI and the Duke of Edinburgh. Natural style and not a hint of contrivance. The archive of photographs is extensive and I would suggest a great source of inspiration
I’m not saying disliking someone should stop one from objectively recognising their clothing choices. What I am saying is if we are talking about style and how this comes across then the behaviours of the person concerned will be a factor.


Hi Simon, I do appreciate your point. I however don’t think we are necessarily talking about the man and the clothes together. My point is that some people are not worthy of our admiration regardless of their clothing. History easily suggests many such figures.
If we are talking about style (not just clothing) which I would suggest is an underlying theme for me anyway) in this article, them I would say the man and the style are synonymous.
Happy to agree to disagree and as always find your articles and the comments always interesting and the latter well moderated.
All the best and please keep up the good work.


Simon, I think it’s different to acknowledge that DoW was an extremely sharp dresser (p much beyond question, I think) when he comes up in conversation or an article etc. for some reason – and to use him as default example when other well dressed men with similar styles are available. Especially as his constant self-promotion and reputation for extreme vanity was a way for him to divert public attention from his sympathies that were beyond dodgy (I know this matters a lot less 50 years after his passing, but still worth bearing in mind)


Great photograph of the Duke of Windsor, Simon. Taken in the dressing room of the Windsor’s country house, Moulin de la Tuilerie, about 15 miles southwest of Paris, it brilliantly demonstrates the mix of patterns for which he was famous. No doubt this ensemble would not have been worn in Paris at the time, but was most appropriate for their “rural” home, affectionately referred to as “The Mill,” because it is a charming collection of 18th-century buildings including a mill house, all of which had been converted. Extensive gardens were designed by Russell Page.

Worth noting is that the Duke of Windsor, arguably one of the best-dressed men of the 20th century, was quite short (Google says 5’7”, but I question that) and very thin. In 1998, Mohamed al-Fayed sold the contents of their Paris home, now called the Villa Windsor, in the Bois de Boulogne (an incredible multi-volume catalog was produced by Sotheby’s and link to NYT article on the sale is below). Included were many items of the Duke’s wardrobe, a number of which were purchased I believe by Brioni, which in turn were sent on tour.

Making a long story longer, a selection of HRH’s clothing made its way to Wilkes Bashford in San Francisco where I had the opportunity to view it up close. The highlight was the morning suit he had been married in, but what struck me was how small the clothing was and how heavy the cloth was (he kept his clothes forever, and these items were probably made prior to central heating). The silver lining here is how such a diminutive man could make such a mammoth impression!


Great post! I think a lot of people in classic menswear aren’t that open minded at all to new ideas. A lot of stores are very old fashioned…black suits has for years been a big no no. Sure, of course it’s better to start with a navy and grey suit but if you interested in style and go for better more luxurious cloths, black could look really good and cool in the right setting. (Saman Amel is one example). Even if I like classic menswear I take a lot of inspiration from other brands and styles. I can take inspiration from Saint Laurent menswear, women collection from Chanel, personalities like Caroline de Maigret and her style. I will not perhaps wear saint laurent clothes myself but I can honest think some people look damn cool in their clothes. Even if the majority don’t look cool, there are a few that really fit in this type of clothes and have the talent to put things together.

D. O'Brien

“The guy on Jordan’s right looks very ordinary compared to him.”
I love it. That cracked me up. One of the best things about your posts, Simon, are your subtle and not-always-subtle British expressions and perspectives. 
*That guy* on Jordan’s right, is 12-time NBA All-Star Isiah Thomas. (I always considered him overrated.)
p.s., I also believe the core to appreciating clothes is appreciating styles that are not your own. I’m glad we don’t all dress alike. Thanks for that. 


Not everyone is a NBA specialist. It is Ray Allen and not Isaiah Thomas btw.


…but compared to baseball and american football, it is pretty global. I know it isn’t that popular in the UK, since you invented football (and then used colonialism to spread it), but basketball is indeed popular in Europe, especially among millenials. Look at the Baltic countries, Spain, France, Italy, Greece, Russia, Turkey, the Balkans. It coexists with football, albeit not as the hegemonic sport. Not all thanks to Jordan, but he hade a huge role in basketball’s dissemination.


The guy next to Jordan is Ray Allen, one of the many people who very much looked up to, and imitated Jordan while growing up (before becoming specialized in 3pt shots). Champion, all star, movie star in a Spike Lee cult movie etc (where he is dressed very well). But I think Simon captured it pretty accurately. Allen, standing next to his Airness at the height of his prime, was probably just happy to be close to the GOAT.


I feel like a four button suit would make a delightful April Fool’s post.


I came for the style but stayed for the writing!

Daniel S.

What a thoughtful, intriguing essay, which inexorably builds to an excellent closing line, Simon–perhaps one of the best I’ve read from you. Cheers!


Yes!! Definitely this!! I love looking at other styles, knowing that some would look rubbish on me but look fantastic on the person I’ve seen. I can never do the untucked shirt thing stylishly and I’d love to try more ‘workwear’ and chore coats/ jackets. Even my children now ask why I wear blue so much so I think I need to play about with some different styles and colours. 
It really bugs me when working in an office everyone says “Oooooo, you look so smart” to the bloke who has just put on a tie but actually looks absolutely ridiculous because it goes with nothing. It’s the general assumption that just because you wear a suit, you must be smart. It ain’t necessarily so! 

Jai Kharbanda

If the suit was too big for MJ, who was 6’6 and 200lbs I can only imagine who that suit was actually intended for!


For me, the choice of clothes is not so much about thinking, but rather that gut feeling, that “oh, THIS feels just right”. Maybe it’s because I used to spend too much time reading menswear blogs, but after all that I don’t need to think consciously about details – it either feels right or it doesn’t. And since it’s a personal thing, it doesn’t have to be the same for other people. I’m fine with others thinking my outfit is wrong, as long as it feels right to me. It is true the other way around as well. I might not think Jordan looks any good here, but if the outfit feels correct to him, what can I say? Same thing with advising people who ask you about clothes. You can give them advice, suggest what would work well on them, but if they don’t agree, there is no point pressuring them. After all, it’s about wearing what feels right.


Let me sum up the greatest dilemma ….
“How do we look great and feel comfortable”

Very often baggy is comfortable but more measured is stylish.
Where is the optimum ?

Particularly in suiting ….. men want ‘sharp’ but comfortable.
Armani does this but then the shoulders can seem dated.
I think Boglioli go some way to achieving this .
Samal Amel also look like they achieve this.


Different styles make this world such a colourful place. And there is inspiration everywhere, even in styles far removed from your own.
I used to work near a London university and everyday I would see the students (mostly East Asian) hanging out in their voluminous clothes, A-line coats and shapeless silhouettes. A bit ostentatious at times, but if you look beyond the brand labels, you’d see they look kinda cool and they carried the look quite well. I went and got myself a balmacaan coat inspired by them. (And this was much before drakes and berg berg were doing them.)
Another extreme example is the label Fear of God. Far from anything ever discussed here. And I would never buy or wear their products. But there’s plenty of ideas in their looks on tonal dressing, tailoring combos with sportswear, unorthodox proportions, etc.


The first and the last point are where most people trip up, because they can’t be successfully faked. And the last can get somewhat sidelined in all the prescriptiveness about what things are ‘correct’ to wear and covet, whether it’s among the #menswear lot or the hypebeasts.

It’s not really about good taste – I’ve always thought Jean-Michel Basquiat was enormously stylish, and thinking about it, he was someone who nailed all 4 (and it did not hurt that he was a spectacularly good-looking young man), and so in his own way did John Galliano, both in his pirate dress days and now, in his more pared-down, rehabbed incarnation. Meanwhile, say, Harry Styles looks rather wishy-washy in his own attempts at experimental gear, but in trying to keep an open mind towards hypebeast looks, I ended up following an outfit account for another boy band who frequently dress in sweats – because they’re also dancers, and it turned out the most hypebeast-y of the lot had a really good eye for colour palettes and coordination …my point being, you’re right that style isn’t about a certain type of look but I feel like the thing that truly tips style over from ‘good’ to ‘great’ is the feeling that an outfit isn’t just flattering to the body but tells me something about the wearer’s frame of mind/personality that day.


Posted this before but it got eaten by moderation I think – points 1 and 4 are where most would-be style icons slip up, they go hand in hand and can’t be faked.

And there is a lot to be gained from looking at styles that aren’t your own, as you said. Hypebeast looks, for instance, are not my thing at all but I love a brightly coloured trainer in suede and there are plenty available for us plebs (Puma Suedes and Nike Blazer low-tops for me) – I picked that particular detail off guys who spend a lot of time dancing, and for whom it makes absolute sense to wear that. Also discovered a love of vintage aloha shirts off them, something I’d previously dysmissed as loud and touristy but which worked beautifully once lockdown came and I couldn’t bear the thought of sweats any more. Stefan above has the right idea – sometimes it helps to look outside the boundaries of what you personally want to wear, for details that could work with your tastes and your life.

Dan James

It always interesting to look at where you find inspiration. After years of white or blue shirts (stripes or checks at a push) I took a risk on a plain pink shirt to wear with a grey suit and black tie after seeing a French politician (N.S.) doing the same and got compliments all round. Recently I have taken to green or burgundy socks and brown suede loafers after seeing them on PS. I don’t wear either shirt and suit or sock and shoe combination all the time but it is nice and fun to do something different for a change.
I wouldn’t wear some of the bright coloured jackets (purple, light blue or pink) that crop up on here but will admit they suit the wearers and might go for a similar cut but in a more subtle shade.
A colleague has a great selection of hats he wears to work; beret, boater, panama, homburg, fedora etc. When I asked why, a reply of “I’m as bald as a coot and I like hats anyway. It’s my style so to speak.” made me think ‘Why, not?’ I wouldn’t wear one all the time but in extremes of temperature, sounds great.
One last thing, the man standing next to Jordan is not Isiah Thomas. Hard to tell for sure but a young Ray Allen looks closer to the mark. Thomas is/was much shorter than Jordan. NBA players of the 90s wore some huge baggy suits which some of them could carry off, MJ being one. Fortunately Jordan, Allen and Thomas wore better fitting suits later in their careers.


If we philosophize about different styles, it fascinates me that what works well and are very chic on women doesn’t work at all on men. Women can wear a black suit, or a black simple blazer with a light blue jeans, a white t-shirt and look fabulous. Put the same clothes on a man, and in 99/100 times it looks ridiculous. Perhaps it’s because women in general are better looking and more stylish. 🙂

Matt Spaiser

Interesting piece. I used to be the kind that followed the ‘rules’ too strictly and thought that made a man well-dressed. The way I see it now is that a well-dressed person dresses with a complete understanding of their clothes and what the clothes do for them. The ‘rules’ come from both a practical and a visually balanced place and generally make sense, but they are too limited. I think a well-dressed person should be able to explain their clothing choices, not because they owe an explanation to anyone but because having that knowledge allows a person to make the best choices for them and it shows in the form of confidence. This can apply to any person, no matter their style, their body or their gender. The idea of being flattered by clothes is only to look more like a mainstream beauty standard, which is to ultimately look younger and healthier and to look the best they can to attract the kind of person they want to be attracted to them. What if someone doesn’t want to look that way? In being purposefully poorly dressed, are they still stylish? I’d say so.

Rob P

Great post! I always appreciate making that connection between clothes and our personalities. Style is more than just what we wear, its also about the hows and whys of how we present ourselves to the world. Too many #menswear exchanges obsess over questions like, “Will a Barbour jacket make me look like a countryside toff” or “will a black bomber jacket make me look like a 1990s West Coast gansta rapper?” Perhaps relevant discussions for mannequins but for living, breathing humans? Probably not. Relax a bit, know yourself (or who you’d like to be), and wear in good health whatever works best for you!

Emerging Genius

It’s evident that your style is becoming more casual. Which isn’t very surprising. More formal attire is definitely in decline.


As my comment is the one that catalyzed this article, I feel both honored and horrified (as in: my hidebound thinking must be the “cautionary tale” we must all learn from).

But the distinction for me is:
What you see in the mirror must also be tempered by (or squared with) how others see you. Deion Sanders is famous for wearing suit jackets with NO shirt (literally, bare chested).

No amount of defined abs or perfected pectorals can justify wearing a suit jacket with nothing underneath. Not even a Playboy model can pull that off.

Sanders had those suits tailor made. They fit him like a glove. But he looked an abomination in those chartreuse or fuchsia fantasies. A more confident man you COULD NOT find in 1994, and a more body-conscious suit you could not find: but he looked like a sartorial train wreck.

My thinking (in what I posted about the farmer’s smock) was that — why don’t we think about fit (as I guess Simon usually does) as the place to start.

I would never hold up 80s Armani as something to aspire to. If I got in a DeLorean tomorrow and went back in time, I would make sure I had something from my closet on to wear. Richard Gere looks great in everything he wears (or what stylists put on him, anyway). But that doesn’t mean that a baggy sack suit looks good on the wearer. It just means that Richard Gere looks amazing in sack suits, or potato sacks. Especially a young Gere as the dude was an Adonis in his prime.

Skaters – or guys who are in great shape and tend to skew thin – can pull off most streetwear: whether baggy or fitted. But I’d argue that thin people look better in clothes that fit them. Just as I’d argue that portly people look better in clothes that fit them.

Did skaters looks good in what they wore, per se? One could write an essay about “otherness” here – and the extent to which the counter-culture both wants acceptance and doesn’t want acceptance. And how said culture (regularly) determines what the mainstream wears because they become glamorized by Hollywood and Madison Avenue (The Rake did an entire spread on skaters a few years ago). We love rebels. I don’t want to look like Kurt Cobain, and I don’t want to thrift old plaid shirts at Goodwill, but he made it look good because he was authentic. He also made it look good because (once again) he looked really good. The same way that Serge Gainsbourg wore ballet slippers everywhere he went: the guy was a God to many people. He was much, much cooler than McQueen. But he (more or less) wore ballet slippers. I couldn’t get away with that. And they wouldn’t look good on me.

But if you take Burdi (the Chicago tailor and clothier who charges 8K for a winter coat), and you have Burdi dress Jordan – no matter what – Jordan is going to make it work (more than he doesn’t). Bijan is a horrible clothier that charges 10 – 20 times what anyone else charges for a suit or jacket and features the tackiest finishes and linings. BUT, Bijan also dressed Jordan (much more so than Burdi did). Again, Jordan made it work for him (and Bijan). If you take a person who is physically perfect by social standards (or symmetrical and who swooped down from Mt. Olympus), then it doesn’t matter what you put on him in terms of fabric and fasteners.

But that’s the problem with this argument, I think. We’re not Jordan. Or Gainsbourg. Or 15 year old skaters with 3% body fat. Or Richard Gere.

We’re mortals who need to shop at The Disguisery more than The Gap (or Men’s Warehouse).

We’re also (thankfully) not Neon Deion with a perfectly waxed chest.

It’s a lovely idea to be eclectic and open, and to diversify, and to find (or seek) inspiration at every turn (it’s also how marketers get us to spend money we don’t have or shouldn’t have allocated). But constantly seeking inspiration for our clothing will:

A) Get us to spend way more money than we should

B) Get us to focus on our clothes in a way that says: we need to be constantly evolving and changing – or we’re somehow dying (?)

My thinking?

I want to move into the next phase of my life (hopefully it won’t be the last phase) with three things at the forefront of my mind, sartorially speaking:

1. Things should fit me right — according to me

2. Things should be easier — I’m tired of this “paradox of choice” (the more clothing I have, the less happier I am with my clothing/closet)

3. Things should (Marie Kondo time) “spark joy” (or something that resembles joy, or is joy-adjacent)

My rear-view mirror?

I just went through my walk-in closet after losing 15 pounds.

My finding?

I didn’t want that stuff anyway.

The question now is: in starting over, what do I really want to build for the future?

The answer is surprisingly simple. And it was there all along.


on your point about a bare chest with a suit..


My word, Zo, I didn’t know this was an actual thing. This abomination belongs in the same category as the “tie-less-tie.”
Apparently, it’s also called the “air tie.” Never understood it…


I agree that someone like Tony is a creative dresser, but he still looks like a grown man playing dress-ups. Whilst this works as dressing-as-spectacle, someone who dresses like this would never be taken seriously in any industry outside menswear, and for me this fails as good dressing.


Completely agree. It’s the menswear costume.


Late to the debate, however, regarding older styles there are numerous trends that many of us will doubtless not return to ; flared trousers ( even if Edward Sexton in his Nutters suit on a Saville Row rooftop ); platform shoes; Oxford Bags, big & baggy 1990 jacket & coats.We may have worn them then or had few alternatives.
As for boxy chore jackets they were originally for doing some form of manual work & were relatively cheap workwear to suit all shapes with little regard to an elegant style but more a matter of practicality. However, at the current cost, variety of colour & materials we might expect a better fit;:I don’t want an ill fitting chores jacket unless it’s cheap & I’m doing manual work.


Regarding Phil’s comments onnclothes, suitability, fit etc. I wouldn’t be too harsh on oneself. When you look at some of the models, their deportment & the fit of some of the clothes I shudder; look at the Drakes site to name only one. Other ‘high end’ offerings show ill fitting ‘fitted ‘jackets with sleeves way past the wrist reminiscent of school blazers in your last year.


Well put, have seen too many of those guys as described in the last two paragraphs, who are utterly religious about certain stuff and constantly frown upon anything that might violate their taboos.


To me, Style is so much more than just the clothes. I think it’s quite interesting that so many men care about so many details of their clothes. The perfect cloth, spalla camicia shoulders, double pleats, expensive socks, bespoke shoes and so on…and too many men don’t take care at all of their bodies, face or hair. Women usually do the opposite, and they look so much better in HM clothes than a lot of men do in bespoke clothes. Of course I think we should care about quality and craftmanship…but it should be more balanced…


The problem with work coats and shapeless clothes is that it’s about a retro look of the working class in the grand epoch , Apache types for instance . Armani was nothing to do with that because he actually gave a style and shape to his baggy clothes .