Am I effeminate? Am I vain? Reader questions on style and its context

Wednesday, December 13th 2017
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It’s taken a while to get to these remaining questions from our ‘You are the interviewer’ post (thanks again for those - some great questions in there).

Hopefully I’ll be able to get through them all over the Christmas break.

Today, we’re going to look at questions of style - how much it relies on context, how others see it, and how my approach has changed over the past 10 years.

If you have any follow-up questions, please do leave them in the comments at the bottom of the post.


Alex: What habits or affectations do you like least in other men who attempt to dress well?

The thing I find most frustrating is clothing that’s clearly inappropriate to particular people or circumstances.

So the young guy in the office who wears a three-piece suit, tie and tie bar, when everyone else is in a shirt and chinos. Or worse, someone who wears a bowler hat every day, despite how anachronistic it is.

Key to dressing well is complimenting the people you are with and the place you are in. It is question of politeness.

Wooster: How does someone look stylish without looking dandyesque and/or effeminate? I love beautiful clothes, but work in a rather masculine environment where such traits are pretty much frowned upon.

And in a similar vein, how do you look stylish without looking pretentious? I’m neither a millionaire nor a country gent, but love the clothes some of them they wear. So how to avoid looking like a impostor?

I think the key is balancing my answer above - on being respectful and appropriate to the place you’re in - and sticking to your guns on the little things.

So men in your office might consider a tote bag to be effeminate. Screw them. It’s just a bag, it’s very practical, and frankly much of their reaction comes from fear.

But you’re never going to be able to dress like Jay Gatsby. Give up on that dream now. Abandon cream trousers, double-breasted waistcoats and spectator shoes.

Instead, take pleasure in clothes that are just as beautiful, but more appropriate to how and where you work. The subtle colours of Harris tweed; the patina of a well-loved split-toe derby; or a coat in a casual fabric but beautiful cut.

Ben: This is a question I’ve always had for those with some position in the fashion industry who demonstrate some self-awareness.

In advocating for a style on such a visible platform, one is constructing a strong identity for himself and attaching himself to a sympathetic community. Yet he doesn’t live merely in that community, but also others to which he presents himself in the clothing that he wears, others who do not share his values, who would scoff at his wardrobe. What’s your attitude toward the latter group?

I’ve always found it useful that I still work in an office, in a modern professional environment, as well as being involved in fashion.

So while I love dressing up a bit for menswear events, being in an office every day quickly brings me down to earth. I learn to push things a little bit, but not too far. To wear a jacket and perhaps a tie, but rarely a jacket, tie and handkerchief together. And always to make them a little more subdued, elegant and subtle in their style.

Often, staff in shops, lookbooks and advertisements should be seen as menus of clothing from which one or two things should be taken, rather than the outfit as a whole.

Joseph: Which piece of menswear would be a good analogy for yourself as a person?

Nice question. I’m going to go for a bespoke overcoat.

An overcoat is something everyone wears (so it will rarely stand out just for wearing one, as a jacket can do) but a bespoke example sets itself apart subtly with its structure and fit. And it can, to a certain extent, be dressed a long way up and down, so it’s very versatile.

I’m sure subtle and versatile must be the two words I use most on the blog.

And ‘interesting’.

Alex: Have there been times when dressing well has made people react negatively towards you?

Yes, absolutely. But more when I was younger. I think I’ve learned the lesson of my first answer, above, slowly over the years.

Today, negative reactions tend to be the basic ones from guys saying something is a little ‘effeminate’ - like the tote bag mentioned above.

You need to have enough self-awareness to know when they don’t know what they’re talking about - that you have a better understanding of how such a piece is seen in the society you live in than they do.

Fergus: I can see an evolution in your style across the life of this blog. I’d like to hear how you think your style has changed through all the experiments you’ve made. Why did you choose certain tailors and cloths when you started and why have you changed your style over the years?

I think this is an interesting follow-on to the previous question.

The first point is that I have learned to dress more in-keeping with my environment and peers. More unusual things like a double-breasted, pale-grey suit tend only to be used at menswear events.

My first ever bespoke suit, from Graham Browne, didn’t get worn that much simply because it was double-breasted. My first Savile Row suit, from Anderson & Sheppard, was a Prince-of-Wales three piece that was worn occasionally but the jacket on its own more often.

Over time my style has become more subtle, and so I’m excited by little things like cloth and texture. A recent example might be my Sartoria Melina leather jacket, which excites me for the beauty and wearability of the dark-brown nubuck.

A: How much importance on a scale of 1 to 10 do you place upon being dressed well (by that you can generally assume tailored attire) and being a gentleman - 10 being of most importance? Does being well dressed really “make the man”? Using a similar scale.

On the first two questions, perhaps 4 and 9.

I think clothing is important but it’s just one of the skills in life you should try to master - like cooking, or creating music. (See post here.)

If being a gentleman means being polite, considerate, caring and discerning, then it is very important. If it means smoking cigars, drinking cocktails and driving sports cars, then it is the least important thing in the world.

And no, clothing does not make the man. It’s more important than a lot of people think it is (it makes people treat you differently, and makes you feel differently about yourself) but it’s still a 4 out of 10.

Other things like health, culture and relationships are far more important, and do more to make the man.

Michael: What do you normally wear when playing or hanging out with your children?

My bespoke Levi’s jeans or Incotex chinos; a button-down shirt, perhaps in chambray or brushed cotton; a cashmere or shetland crewneck sweater. On the feet, boots, derbys or trainers.

A: Has PS made you vainer?

Yes, absolutely. I fight hard against it, and my friends and family are very good at bringing me down to earth, but it’s hard not to be affected by seeing your photo on a magazine cover etc.

I’d like to say it’s given my confidence rather than made me vainer. But I’d probably be wrong.

Certainly, the people I respect most in the industry are those that are the most honest, approachable and real. And the ones I dislike most are the preeners and posers.

I often try to smile in my photos to avoid the impression I’m taking myself too seriously. And I don’t think people that have met me in person would have that impression.

BespokeNYC: Recently it feels like there’s been more focus on casual pieces (or less businessey anyway) on PS, but perhaps that’s simply because business pieces are always going to be more limited in range so your collection is more “complete” now.

That’s a good point - I think the slight shift is just because I have spread out to find other things interesting, that all relate to the same sense of style. So fewer straightforward Savile Row business suits, and more which type and make of jacket works with jeans.

One thing I am always doing is experimenting with other types of clothing to see if they fit into my sense of style. And often rejecting them.

So on the formal side, perhaps a fur hat or astrakhan that I decide is too fussy; or on the casual side a denim chore jacket, seeing if it works with smarter trousers, and deciding it doesn’t.

I think you need to establish a sense of your own style and wardrobe, so that a lot of it works together, but then always test its assumptions with new things you see.

Ansgar: What is your idea about the budget for clothes? Some people stick to a 5% (of income) rule. What is your opinion?

It’s a little complicated, because a lot of it I justify as being part of the research for and coverage for the blog.

But I’d say it’s probably better to look at your absolute disposable income. So after you’ve paid for mortgage, food, travel, utilities and everything else (for you and your family). I’d say I spend about 60% of that disposable income on clothes.

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Is that 60% of disposable income also after saving (in mutual funds or whatever) or is that what the remaining 40% is for?



Hi Simon
I’m a little older than you (44), we met when Elia visited the first pop up earlier this year.
I think like a lot of other things to dress well you have to know yourself and stop yourself from getting carried away; like you I’ve come to really appreciate the little things. I love the statement pieces that you’ve had made but the casual Neapolitan jackets and shirts are pound for pound the most valuable items you’ve commissioned. The way things are moving do you think that they will be your most used items?



If I could ask for one Christmas present, it would be some pictures of the newly converted pea coat with its brown buttons. I would just love to see it.

Thanks also for a fantastic and insightful article, as ever.


I second James’ request. I think the only pictures (and only from upper-chest up) are from the Begg square bit. You get a sense of the new tone of the buttons, but I would also like to see the effect of the new buttons with the dramatic shape of the pea coat


Hi Simon, just wanted to point out there is no post linked here
“On the first two questions, perhaps 4 and 9. As in, I think clothing is important but it’s just one of the skills in life you should try to master – like cooking, or creating music. (See post here.) ”
Personally, I like that things are moving away a little bit from the business focused side. This is only due to the more casual pieces being more applicable for me in my daily life.


Thank you for this article! I enjoyed it!

Best regards

Don Ferrando

Dear Simon.
When would it be apropriate to where a bowler at all. And what clothing does it require?

Don Ferrando

Thank you for your answer and advice.
I always considered a Homburg more formal than a bowler.
Maybe a german point of view?


Simon, You have neglected to mention the classic bowler hat and white boiler suit combination.


Some interesting comments in your response. On the tube this morning a young lady carried a bag with a quote from Dali on it, something like ‘ I worked out who I wanted to be and now I am that person’. Cary Grant dressed and affected certain mannerisms to the extent that he became that person i.e. the old ‘everyone wants to be Cary Grant’ quote. I think that clothes in the right environment have a much bigger impact than most people think. As you state they affect the way that you feel and behave ( try putting on a Huntsman bespoke jacket without automatically standing taller ). Its acknowledged that really stylish people are those that are comfortable in their clothes ( Noel Coward arrived at a writers event which he mistakenly thought was a black tie affair and said to the astonished group ‘ Don’t feel embarrassed because you inappropriately dressed !’). Stylish people wear a combination of clothes and confidence lightly and make you feel uplifted by being in their company. Being a gentleman is more than just about relationships. Its about putting people at ease. Knowing your way around a wine list may not change the world but in the right environment it can give people just a little more pleasure with your company. No bad thing !
Ps like a lot of readers I very much look forward to your blogs. Keep up the good work.

Peter K

I saw an interesting article yesterday about performance on exams when wearing more formal clothing.

The researchers found that more formal clothing seemed to evoke a greater ability to think in abstract terms – so superior performance in maths for instance.

Interestingly the effect occurs when there are differences in the clothing exam takers wore. When everyone dressed the same the effect disappeared. Like so much sociological or psychological research cause and effect are hard to separate. Still it made me wonder if certain clothing asks you to “live up to it”.


Ha! For a second I thought this was some ridiculous thing about Eton wearing morning coats and other private schools wearing suits etc.


Perhaps a subconscious sense of having an “edge” plays into it? Hence the effect disappearing when the perceived edge was lost (with everyone wearing similar clothes.)

Art Shenkleman

Hey Simon
Insteresting blog – vanity, gentlemen etc. What’s your view on people being mean, tight, stingy – do you think it matters to be generous or is wearing a great outfit enough?

Art Shenkleman

Agreed, Simon.

The outfits are great and the blog interesting.

However,, many of the brands featured (more than 5) have annecdotedly told me that you are mean and have previously stated that the importance of others buying you drinks,
Meals etc.

In fact one described you as the “stingiest man in fashion”.

Others tell of the pressure they feel when you request them cut you a jacket gratis or provide clothing maintenance free of charge.

Keep up the great blog but drop the Scrooge, Simon, as Christmas is just around the corner.

Happy holidays!


If Art’s comments are true I do not believe the blog would have grown to the size it is and so many brands would still want to be part of the pop up stores, symposiums, events, books and collaborations. Business is a small world which ever industry you are in and being mean and parsimonious does not lend itself to success.

Art Shenkleman

Thanks, Simon.
Nice of you to respond as it was a genuine comment and not meant to be rude.

I’ve dropped you a note direct with names and comments as all are genuine – a number of people seem frustrated by this.

Seasons greetings,




Did Art actually provide any details? Were there any merit to his claims?



Not that you need anyone to defend you – but given how generous you are with your advice to readers, how much of a non-judgemental environment this is (even if some of the comments posted are beyond snobbish) and how it seems to appeal to both the ignorant (me) and the better informed (me in a few years hopefully) I find it difficult to believe that Art’s comments have any grounding in truth.

To be honest, I’m amazed you even gave them the air time. They’re hopefully no more than a sad indictment of the way some in our society see fit to behave, and interestingly given some of the original questions in the post, the complete antithesis of what I believe it means to be a gentleman. Trying to shame someone so publicly amounts to little more than bullying.

Therefore, as a new reader I wanted to thank you for answering every question I have posted this year, irrespective of the fact you’ve probably answered them all a million times before. Generosity doesn’t just extend to money, and arguably time is more valuable, especially when you have two young children.

Keep up the good work.


As a long-time follower of your blog, to me Art’s comments ring very hollow and fly in the face of the extensive generosity you have provided us readers over the years by giving such invaluable content in your hundreds of posts. Do keep up the good work.


Blimey Simon, you must have skin thicker than your Edward Sexton overcoat at this point.

I can only echo the warm tributes of the majority of your readers. Keep up the fantastic work.

Walter asickinger

“More vain” is much more elegant phrasing than “vainer”


Have you ever bought clothes on your credit card?
It’s hard to resist some things!

George Dunnett

Many thanks Simon for your wonderful posts this years, I’ve learnt so much.

One quote I like to use regarding dressing well is ,

“If you can’t be bothered to dress well, what else can’t you be bothered to do”.
If has evolved from… “if you can’t be bothered to polish your shoes, what else can’t you be bothered to do”.



I think you should address Art’s comment above. It is commendable that you allow even such rather rude comments be published here, but just leaving it unanswered may leave the wrong impression.



Strange you need to you ask if you have the answer already 🙂


My remark was meant as a comment to Art’s question & answer a little further above:
Strange, that you need to ask Art, if you already have the answer 🙂


Hello Simon
I can see the merit in much of the advice here regarding such issues as; having an appropriate look in a given context, and making those around us feel comfortable.
However having taken early retirement a couple of years ago, I have to say that one of the great joys of reaching this stage in ones life is the wonderfull freedom and joy to wear whatever one chooses, and if sometimes that might be a little different than the norm then vive la difference.
Thank you for your splendid blog, it can be quite an inspiriation.


Thanks for entertaining this reader’s inquiry 🙂

Nick Inkster

I absolutely agree that it is simply the right thing to do in matching your dress to the circumstances; I’m on various boards around the world and in each country there is a polite convention that you follow when it comes to your outfit.

When circumstances are such that there is no expectation among others as to what you should wear, then it is entirely up to you. I have an old Guernsey sweater that was a mainstay of my student wardrobe in the 70’s (believe me, they were fashionable they), which is now more a series of holes held together by threads of wool, but I love to wear it when I can because it just feels so good.

Bizarrely, it attracts quite a number of compliments.

Louis Winthorpe

Interesting comment, Nick. What sector do you work in?

Nick Inkster



@nick .. It could be that the jumper makes you feel better about yourself therefore you behave differently and as a consequence people notice you and it more.

Peter K

I also greatly appreciate the articles on mixing casual and formal clothing. My office is very much a “business casual” environment and your thoughts on this type of dressing are very helpful Simon.


When are you going to be in the pop-up this week?


“Abandon cream trousers, double-breasted waistcoats and spectator shoes.”

To clarify, you mean the combination thereof, correct? You’ve been pushing cream trousers for years now.

David Man

“And no, clothing does not make the man. It’s more important than a lot of people think it is (it makes people treat you differently, and makes you feel differently about yourself) but it’s still a 4 out of 10.

Other things like health, culture and relationships are far more important, and do more to make the man.”

I love this.

Great article and good honest answers.


I am occassionally critical of Simon but do it directly by challenging arguments he might make (and I have done this many times). However I think it low passage to ask of a situation as Art does when you have knowledge afore thought… it looks like an attempt to entrap. As for the gossip – doors would not open – and stay open – for Simon if he was mean and grasping. As a long term reader I would not bother if Simon were that way inclined as such his character would bleed through the prose and the way he addresses criticism. It might be that some have an issue but professional jealousy is everywhere. The higher Simon climbs the more others will envy. This is particularly so in industries such as fashion, media and entertainment (I have experience) all of which are riven with the politics of envy and snobbery. I have to say Art that your comments come off as some dubious, misjudged frat boy hazing technique and are quite personal even though your evidence is heresay. It belongs elsewhere.


I thought my question was inane merely five minutes after submitting it.

Much thanks for entertaining it together with the others’, Simon. Always a pleasure to discover more about the way you think and look at life.


There are still individuals who wear bowlers?! I’m guessing that it’s confined to Britain?



Try Northern Ireland around the 12th of July. Usually worn with a fetching orange sash.

Romanes eunt domus

Not really: I am a German living in a small rural town in Germany and I love my Lock & Lock when I am wearing a double breasted overcoat.


It’s difficult to find a balance between dressing well and fitting in. For example, men seem to have abandoned the tie wherever possible, which is sad because ties look good; I find when I wear a tie these days I’m sometimes asked if I’m going to a wedding (LOL).
On the other hand, I agree that if you go too far in dressing smart, you and everyone else can be made to feel uncomfortable.
So we need to find that sweet spot between over dressing and following the crowd.


This is true – and it’s a shame that environments where a tie would have been commonplace 5-10 years ago (such as my workplace, a City law firm) now see 80%+ of men go tieless (with many retaining a suit and open-neck shirt).

I take the view that wearing a tie in such an office isn’t out of place – as Simon suggests, wearing a 3-piece suit , bowler hat and/or perhaps a pocket square probably would be overdoing it. The same issues arise with accessories as well as clothing. For instance, although I’d love to get myself a Swaine Adeney attache case, that’s just not going to work in a modern office…


As a long-term reader of this blog and occasional commentator, I am disappointed that Art chose to make his comments public, surely a private response would have been more appropriate as the comments tend to the individual and not the commercial, the arrangements for which have previously been made crystal clear by Simon. Having consulted in the textiles and clothing industries some years ago, I can only concur with the previously made comment about the negative and highly personal way some chose to respond to those with a reputation and profile that they consider greater than their own. As another commentator has said, the traits described would surely have spilled out of Simon’s writing, that they have not would question the veracity of the accusers.


Hi Simon,

I’ve appreciated your candour and detail in this article.
One of the things you say is that one should “Abandon cream trousers, double-breasted waistcoats and spectator shoes.”.

Do you mean wearing these pieces all together? I’m a bit confused by your inclusion of ‘cream trousers’ given that you both wear them and praise them relatively frequently on your site. I have become fond of cream as a versatile colour.

All the best

Anders T

Some reflections.

First item regarding, eventual wearing of bowler hat vs Homburg, fedora or trilby. Personally I feel that the bowler, is pretty much out of date these days, even if it’s appropriate during certain gatherings and these would probably be obvious, as somehow official.
The Homburg is, in my humble opinion more formal, than fedora or trilby. However there’re more to consider, for example where and when. If you wear a Homburg at a daily basis, your colleagues probably, will consider you an “odd ball” the first two weeks, but if you persist, they’ll eventually accept it, as your own gimmick. The turning point is up to you. Do you’ve the confidence, endeavor or/and courage, to wear it long enough?

The second item, will take some time to comment, it’s the eternal question; who’s a gentleman and who isn’t…………
A gentleman is a gentleman, even when he’s naked and an (apologize for the language) asshole is an asshole, even if he wear bespoke.
The question is however who decide? The answer is simple and/or difficult, but one thing is very clear. It’s never yourself, it’s always someone else. It’s the very same as the manager, who talk of him-/herself in third person, as a leader, only because they have attended, a weekend course called leadership training. You can also compare, with the difference between the intelligent and the dumb, where the intelligent know, that he actually doesn’t know anything, but the dumb, thinks he knows everything. A summarize from my winding brain is by other means, if you’re a person that other people like, and often ask for advice, what so ever, could very well be a gentleman, and if you dress nice as well, you’ll be on top of the world, as a well-dressed gentleman, and in that case, my sincere congratulations, because you’re something or should I say, something else!

By the way Simon, we don’t always agree upon everything, but your column is almost always worth reading, so keep up your elaborated writing, and from an elderly gentleman to another young one, sometimes it feels good, to ask “gossip lads” and likewise, just go drown themselves. Maybe not so “gentleman spoken”, but in that case, we’ll survive anyway


“And no, clothing does not make the man. It’s more important than a lot of people think it is (it makes people treat you differently….)”.

A sentence worth exploring in its own right. How does it make people treat you differently? In a better way? Or in a negative way?

There is always much to read on how clothes make us feel but not quite so much on how they affect those around us.

Definitely one to take a deeper dive into…

Matthew Dallow

A pity that the bowler hat is viewed as anachronistic. Not only was it made for practical reasons – for safety I believe – but to my eye one of the most stylish hats to have been worn, and worn by members of all classes and even a royal (Edward VII) and both sexes. I think it looks particularly good worn by women. It’s even become traditional headwear for certain South American tribes people.

I think though that pretty much all headwear looks a bit try-hard these days. Even the sight of that most distinguished gentleman and often buffoonish Geoffrey Boycott speaking at the WACA on this very day was making me wince a little even though his Panama hat has become something of a trademark.

I find it strange that the fedora, trilby, Panama, baker-boy and even pork-pie hat all get off lightly and are viewed as credible with varying degree while the poor old bowler is seen as old-fashioned. I associate all of the former with high-fashion and hipsterism except perhaps the Panama which is practical in context and the bowler as just a little eccentric, and there’s hardly a more English character trait than that.

I say bring back the bowler hat. I shan’t be doing it though – I look quite ridiculous in all headwear.


I think a Trilby or Fedora which doesnt have an extremely flamboyant brim all look great dressed up or down and are very practical. I live in E Europe much of the year and believe me you really treasure wearing one with a biting cold wind blowing past you!

I agree though that a bowler looks fantastic with a sharp dark suit but you just cant get away with wearing one these days as its just too anachronistic.


The last time I saw a gentleman wear a bowler hat in London (other than on military parade) about 20 years ago at a tube station, he was being harassed by a couple of youths: an example of the shameful practice of “posh-bashing”. I think that is more the reason why they are no longer worn. Strange how hats seem to create an atmosphere: I used to wear a Homburg and got strange looks as though I were a murderer, but a top hat meant that crowds would part on a busy pavement.

I think on the question of anachronism, everything depends on perception: if you were young and had film-star looks and wore a bowler with confidence, it would be considered a fashion statement; but a short, dumpy and plain man would be the object of ridicule.

James Dowdy

I’ve been following you for a long time, and find this to be possibly the best post ever.


Simon – I hope the volume of readers on this thread praising you for being civil, self-reflective, capable of taking constructive criticism (and managing non-constructive criticism) and being positively engaged with your readers hits home and that you feel it is well-deserved (it is from my perspective). Otherwise, you write beautifully, including in this post, about aesthetics in a way that I find explains why they are important without inappropriately elevating that importance. It is masterfully done. Thank you.


Maybe I’m young but

Bowler hat= Oddjob from James Bond.


That was a square-crown bowler, or Cambridge, not the standard town Coke. Churchill often wore one and they are, I think, still made by Lock’s but perhaps as a special order as I don’t see them on their website.


Simon wheres the hairy brown tweed in the photo above from? Looking for a nice tweed cloth in a brown shade with some real texture but having a hard time in the usual cloth books.


This is my thoughts about Arts comment.

First of all, I dont know any details about his conversations.

But I have met Simon twice and had a real conversation once. I think that he was extremely polite and down to earth.

I also know some people in the menswear business. The people that I have discussed Simon and PS with considers him very professional and polite. The ’best’ of the menswear journalists.

I also understand why some people may have a different opinion. Most fashion journalists only write positive articles about brands and artisans. Even specialised magazines like the Rake and Plaza Uomo only write positive pieces. Simon is never mean in his reviews but he can also be critical. That is something that I expect from a journalist, unfortunately uncommon in fashion journalism.


In London, is it appropriate to dress down in a tweed jacket (much like what you’re wearing in this article) — without having someone ask you whether you’re just in from the country?


I was wondering if you’ve ever written an article on how to look good in an alpine enviroment?
I often struggle with this; the discrepancy between pictures of Agnelli in the alps in the 60s and my own “useful, high-tech” clothing is a little to big for comfort.

Any tips on how to improve?



Bowlers are still commonly worn at Puppy Shows.


While I agree that it is polite to try to fit in I have given up on this. I work in IT startups, fitting in would mean worn-out trainers and grey t-shirts. Thank you but no thank you.

Tried on a bowler hat at Lock’s the other day – deal with it.


I only discovered your website today but I really like the content so far.
I have similar “problems” as you mentioned; I work as an IT engineer in an office where most employees (including managers) get away with jeans, t-shirt and a hoodie, so while I like nice clothes, I must be careful to not look out of place – a white shirt and a V-neck sweater or a turtleneck and a sports jacket are probably the most formal pieces I’d wear. I don’t even wear chinos, just some plain black tapered jeans. So I can totally relate to what you mentioned and I’m looking forward to finding some inspiration here.


I’m not sure why it has taken so long for me to find your site. Fantastic.

I get what you are saying about dressing appropriately for where you are. For the most part, it is only polite to make sure others are comfortable. I certainly take this into consideration when I’m meeting with a client. As a woman in a stereotypical man’s field (civil engineering), it’s a delicate balance. I never want to look frivolous. I don’t mean bows and lace or stiletto heels, but the look that I spent much on what I’m wearing. My clients as a general rule do not.

But on the other hand, I think that how you feel in the clothes may be more important. Your comfort level is what helps others feel comfortable. I used to work with a young gentleman that had a very sharp sense of style and was able to wear color and blend patterns with aplomb while still looking professional. He was very comfortable in his skin and clients were disarmed by his ease. I don’t sense that I could get away with that (however comfortable I feel in something or perhaps simply due to my impressions that I couldn’t get away with it) but I enjoyed his sartorial choices.

Ian A

Sorry I didn’t understand your aversion to the bowler hat! Before I became interested in menswear I wore a Northface Mcmurdo parka and beanie hat almost exclusively throughout the winter and the sneers of “ Oh! Are we off mountaineering today” kind of led me inadvertently to your blog and others like it! Needless to say these days i’ve ditched my urban hiking look.

Providing someone has a square face a bowler hat would look great with an overcoat in a city setting!

Mike G.

I cringe at my dressing habits from just a few years ago. I definitely overdressed for my work environment.


Why do you think wearing a 3-piece or something anachronistic in a certain
context is impolite?

Mats Larssen

Hi, Simon.

Found this old post on your site while rummaging through the archives and it made me think about a dilemma I find myself to be in.

I’m a man in my early 40s and I’m overweight and have always been overweight. The last 10 years or so I’ve lost a lot of weight (in a healthy and good way) so some years ago I discovered that my whole wardrobe was basically way too big for me. Hence, I had to get a new wardrobe and that started me on a sartorial journey that I’m still on (my way of dressing before/after this cleansing of the wardrobe could hardly be more different). It’s been quite a ride, as my background invested me with nothing at all when it comes to dressing well.

On this journey, I’ve learnt that for people like me (i.e. overweight), there are certain types of clothes and styles that flatter me way more than others. So my style these days are mostly sport coats, shirt, odd pants, ties or bow ties, pocket square and nice shoes. I’ve found that I also enjoying wearing headgear, so in summer I usually wear one of my two Panama-hats and the rest of the year either a flatcap or mostly one om my three Fedoras. For outerwear, which is often needed since I live in Norway (and therefore excuse my English), I usually wear various coats, including a nice trench-coat, a loden-coat and various other coats.

Reading this post you, as I’ve seen you do before, highlight the point that you shouldn’t dress too out of style with the enviroment that you live in (both socially and at work). I agree with that, in principle. But here is the dilemma: If I wear what I feel well in, described above, and what looks good on me, I’m already way over-dressed for the enviroment I live in. Because the people I deal with in my day-to-day life usually wear denim, sweaters, athletic sneakers and all-weather-Goretex-jackets. (the same I used to wear before the cleansing) Putting it at a point: even wearing my least formal shoes, a brown suede full-brogue derby, already transcends the norm in the enviroment I live in.

Put if I wear denim, sweaters and athletic sneakers I don’t feel well in those clothes. A sweater is not flattering for my body (due to being overweight and that weight mostly showing in the mid-section of my body) and denims are usually low-rise – so if I wear denims and a sweater I end up looking a bit like a stuffed muffin or like I’m wearing a kaftan. That might be flattering for some small sub-section of humanity, but I would personally like to avoid those looks.

Of course I could drop the tie/bow-tie and pocket square and just go for pants (usually high-rise with suspenders), a shirt and a sport coat. But that would already be moving so far out of the zone of my enviroment that adding a tie/bow-tie and a pocket square really doesn’t make that much of a difference (it’s the difference of transcending the scale by 95% instead of “only” 87%).

I’ve therefore made the choice to dress in a way that I feel comfortable and well with and hang the consequences that I clash with the enviroment I live in. Still, it is a dilemma, and I wanted to point that out and if you have any thought to add to it, it would be really interesting to hear.

And, by the way, the dearth of writing about style for people that are overweight and, espescially, how hard it is to find proper, nice clothes for people like me continue to amaze me. Why haven’t any brands really tried to target the market that is overweight men and where things like high-rise pants, sport coats and the likes are really the most flattering things we can wear?