How a hat should fit (with Stephen Temkin fedora)

Wednesday, February 7th 2018
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Every man thinks hats don't suit him. Yet every man, of every shape and size, used to wear a hat - and they looked good. Conclusion: men don't know how to pick a hat. 

I know I've run through that before, but it bears repeating in the name of re-popularising the hat.

Hats are hard to wear today, given no one else does so. But they certainly aren't anachronistic, and they are very practical: warm, excellent rain protection, and not as awkward as an umbrella. 

So how should you pick a hat? Well, first of all ignore the brim and focus on the crown (the top). 

Broadly, this should echo the shape of the rest of your head. If you drew an oval around the bottom of your chin, past your ears and over the top of the hat (as I have done above), the crown should sit cleanly in that oval, reflecting the shape of your lower face. 

So if your face is long, you need a taller crown. If it's thin, that crown should taper (so it's thinner at the top). 

In the picture above, you can see the height is pretty good for my relatively long, thin face.

The front view (below) is also pretty good, although arguably the crown could be tapered a tad more.

Most hat shops don't offer a big variety of crown heights and shapes. Given they also need to vary the colour, materials and brim width, it may not be practical to have many. 

So rather like finding a good shoe last, you may have to try different brands to find a crown that suits you.

Once you've got a sense of the crown shape, consider the width of the brim.

This is far more subjective, and driven by style and formality as well as bodily proportions.

So I wear both trilbies and fedoras, for instance, with the trilby pretty much always having a smaller brim. The trilby is also generally seen as a more casual hat, partly because of that smaller brim. 

However, the proportions of your body and the clothes you're wearing (below) should also be borne in mind. 

I consider that I can wear a slightly larger brim because of my height. A smaller man might look slightly top heavy and disproportionate in a big fedora.  

I also tend to wear a hat like the one pictured (from Stephen Temkin, aka Leon Drexler) with longer, more structured clothing. 

It looks fine with my big-shouldered Sexton coat - indeed, I could probably wear an even larger brim (perhaps 8cm, the Temkin being 7cm). I have a charcoal hat from Anderson & Sheppard at that width that works well.  

But that A&S charcoal definitely looks too big with a raincoat, for instance, or a raglan-sleeved coat. 

I should say again that these latter points on brim width are much more subjective. Benedikt at Shibumi is much smaller than me and wears big brims with aplomb. 

They also apply less when the hat is worn on the back of the head (more casual, and not something I like on myself). Agyesh at Stoffa and Jamie do this well. 

But the factors you need to consider - bodily proportions, formality and (with the crown) shape of your face - are not in doubt.

If you want to find out if you really are a man that can't wear hats, these are things to look at in the mirror. 

A few details on the hat - for I've never done a full review, following my initial post back in 2016

It was made bespoke by Stephen, who works out of his home in Toronto, Canada. The company name is Leon Drexler (a composite of his father's first name and mother's maiden name). 

It is made in beaver felt with an angora finish (the slightly longer nap on the surface). This gives a slightly more casual effect, and requires occasional brushing to keep the hairs separated and stop them matting.  

More details on the making process in that original post

I have what's known as a 'long oval' head, and with ready-made hats usually have to size up and then use foam pieces inside the sweatband to fill out the sides. 

Stephen managed to partially correct this in his hat, but it's not easy - hatmaking requires a solid wooden block for every size and style, so bits must be added to the block to adapt it. Stephen does it using (very Canadian, this) hockey tape. 

I couldn't be more pleased with my hat, with the fit, the material and the style.

The colour is more muted and urban than most greens, and I like the little design touches such as the flat, square bow at the back of the head (shown above) rather than something more decorative at the side. 

Some details on Stephen's service:

  • Felt hats start at C$625 and take around 20 weeks to make - this is current backlog, which is a little longer than usual. 
  • Additional elements like curled brims and binding add C$15 to C$120  
  • Fittings are not usually needed but a visit with the finished hat can be useful
  • Stephen does take orders by phone or email, with the customer measuring their own head and making decisions remotely about colour and style
  • More on the Leon Drexler website

I am also wearing: 

  • My Edward Sexton overcoat, which has had five inches cut from the bottom. It is much more practical now, but hasn't lost much of its drama. 
  • Wispy-square scarf by Begg & Co (a piece I designed for them - available on their site here)
  • Black silk umbrella from Michel Heurtault
  • Brown-flannel trousers from Anderson & Sheppard
  • Dark brown ('bronze') monk-strap shoes from Edward Green

Photography: Milad Abedi @milad_abedi


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Dermot McLaughlin

I moved to Lisbon in 2016 and I was pleasantly surprised to discover that the wearing of a good quality hat is still relatively common amongst Portuguese men in their early middle age and older. It is one more small reason amongst many for loving this place.


I like the new length of the overcoat…. good choice!


Excellent article Mr C.

The more that I wear hats & caps outdoors the more that other people without seem to me to be not-completely dressed.

Thank you for the useful analysis of crown & brim proportions. It seems obvious now that you explain it but hats also merit a shape & size suited to the individual wearer.



I remember when I first wore a trilby I was a little self-conscious…. I guess I must have imagined people would stare at this alien headgear.In reality,I’m sure nobody is remotely interested in my apparel and it was ridiculous to be sensitive about my new hat.I now always wear one in winter and feel a helluva sight warmer than without it.
Be brave guys,go for it!


Its interesting you say everyone can wear a hat. One of my style icons, Cary Grant decided, even when the height of fashion was to wear hats – they just didn’t suit him. He suggested that his very broad neck was the reason, though to that I would add he had quite a broad face too. He was in an old film the other day and did start out wearing a fedora – and he was right it didn’t suit him. Having a rather chubby face I decided several years ago that hats were not for me and I remain steadfast in that belief; if I was to take your oval as an example I think the only hat that would fit into that would be an old “pork-pie” hat much favoured in the 1950’s and 60’s but not so much now.


Very interesting point on how all men used to wear hats.
I tried on stoffas hats on the last trunk show, but I’m not sure it would fit me. The crown feels very high, yet I’d imagine it’s pretty much the same height as yours. Maybe silk band helps to visually breaking the height off slighlty. Plus I imagine wearing any hat requires some sort of getting used to.


How should one think about color coordination between hat and coat?


Simon, thank you for your response to my post. I got the quote from a fabulous book called the Cary Grant Style that I can recommend to you and probably all the readers of the site. In it their are a couple of pages of Mr Grant in varied hats and the only one that worked was a top hat. My other style icon is Bruce Boyer though I have to say his Marol shirt collaboration is making me rethink that. While the shirts are perfectly fine and typical of the BB style the price for an upmarket ready to wear shirt is, I think, ridiculous.

Peter K

I have a small oval head and I find most ready made hats are simply to big for me. I did try on a “stingy brim” fedora once that looked very good but lacked the courage to buy it and wear it.

I do wear a flat cap and it looks good on me. Having a s mall and narrow face it is a challenge to find one that is narrow enough to not make my head look like a mushroom when wearing it.


Sorry for disagreeing and I apologize in advance for any offense incurred by my commments but I cannot abide by the idea that all men look good in hats.
Can’t help but feel the outfit looks as if it part of a ‘costume’.
Perhaps it is the dramatic flair of the overcoat itself but also in combination with the wide brim of the hat but I get the feeling you are going to fight crime with Dick Tracy.
Again, my apologies for the negativity in my remarkks but of course this just one mans opinion.


Simon, I think you look very dapper and would go so far as to say that you look better in a hat than without it, especially in profile. I always wear a hat of some sort (being another baldy) and feel semi-naked without a head covering – although I find that flat caps are the most practical since you can roll them up and hide them in your coat pocket when not needed. Good article with sensible advice.


Simon, you look very cool with your outfit in the photograph! Your wide brim hat will indeed protect you from rain, but I’m curious to know what happens to it after repeated showers. I always have a hat on, or my Purdey cashmere tweed cap. Although I love my H&H and Christy trilbies, because I’m brutal on my clothes (my E&R Panama has a sliced cut from careless fastening of its brim), ny dream hat would be Drake’s which can be folded – have you checked it out? If I check in my coat at a disco garderobe, I’d prefer to fold my hat and put it in a coat pocket. I image foldable hats are tougher? Do you know that Drake foldable trilby? And because the Panama is so fragile,
I’m considering linen – what do you think?


I wouldn’t go so far as to allow words in my mouth (social acceptance of hats) but perhaps teetering on anachronistic is more appropriate ?



Doesn’t hats also work best for bald / very short haires people?

I won’t wear one as it would mess up my ‘do for the rest of the day (when I’m in the office and not wearing a hat).



Very interesting theory on the shape of the crown mirroring the face, but I’m struggling to understand how to put it into practice. Doesn’t pretty much any hat create an oval shape around the face? Perhaps you could show some examples where it *doesn’t* work so we can get a better sense of how the principle applies…?

Ian A

I’m 5 feet 7” with a square face do I bought a dark Brown beaver trilby rollable hat from Bates in Jermyn Street. It fits in with my long Overcoat and oddly in London with it’s general Zoo like sartorial weirdness nobody seems to stare or particularly notice it. It’s practical nice and warm goes with my non sport themed attire and even my non hat wearing colleagues liked it. Some said I looked like a detective but that has to be better than an Al Capone connotation.

I did try the bowler hats but didn’t feel comfortable with it and the Fedora dwarfs me. I was wondering what colour I should go for next? Possibly a light Grey but then i’d Need to think about co-ordinating gloves and scarf.

Hat & Glove wearer

Simon, would you agree in regard to what you’ve stated about hat colour is in fact your opinion for glove colour, too?


Try wearing outside London pal! I bet you a tenner that it won’t be 5 minutes before someone either asks you if you’re going to a 40s themed fancy dress party or shouts “Michael Jackson!” at you in the street.

Saying that, it does seem odd that older gents can wear brimmed hats in public and no-one bats an eyelid?

Being able to wear hats and pocket-watches is one of life’s small consolations for getting old.


The hat and coat do not quite match. The coat is military in form and more sombre in grey. The hat in light brown has a luxurious nap – more suited to be matched with leather, or, at a stretch, country clothing (think Orvis), I know you will disagree Simon but I think the Loden overcoat might have been a better match – it would certainly have more elan. As for the coat it was better at the previous length, more modern now, perhaps even more practical but still wrong. Some items defy fashion due to their pragmatic nature. A lot of your wardrobe is ‘city’ wear but a long coat like this is better matched with quality boots for the very coldest of days. Now cropped it looks shorn of its full practicality and thus compromised in design.

New to The Site

I would argue hats are far from their demise. The fact that your custom milliner has a 20-week wsitung period and can charge arguably very high prices for his work suggests the contrary.

Wear it loud and proud and it’ll look good .


I’d love to get a panama for summer, especially as the hair isnt as thick as it once was, and suspect it’d be a gateway to other hats but with a round/chubby face and a 65cm (uk size 8) head there are so few options and as I am not convinced I can pull it off I don’t want to pay bespoke prices.


Anyone who wishes to wear this sort of combo is of course free to do so. Yet, doing so, is going to attract the ire of one’s colleagues! Indeed, SC looks akin to a character in a Foyle’s War episode. And i doubt he would ever wear this to work.


It all depends on the job, and one’s position. This goes for all clothes, not just hats. You don’t wear a double-breasted pinstripe unless you’re upper management (no, Mr Crompton, you just don’t), no matter how good it may look. It’s just not done. It’s a principle which no longer dares speak its name, called sticking to your station. Some of us will just have to wait a few decades (by which time we’ll be ole and decrepit) until we rise enough to be able to wear a hat to the office.

Ian A

I work as a Supervisor in a rough blue collar job and I often wear a dark brown trilby with a navy double breasted overcoat or trench coat. But then I work in London where all types of fashions and national costumes are worn.

I’ve only received positive comments from work colleagues and the only group who laugh at my hats are goofy teenagers in ripped up jeans and I’m not sure their opinion is valid when they cannot offer a feasible alternative for smart city wear.


Simon, in your post of 13 December 2017 you said that it was anachronistic for people to wear bowler hats, and you seemed to criticise people for doing so.

Whilst I’d much rather wear a fedora than a bowler hat, and indeed I rather like the look of your fedora, I’m afraid the wearing of all these sorts of hats is anachronistic. Walking around the City, how many people do you see, these days, wearing these sorts of hats? An insignificant number. On any given day probably zero. Admittedly, the fedora is warn more commonly than the bowler, but it is still extremely uncommon. By the definition of the word, I therefore think it is anachronistic, and that is why it is difficult for people put on a fedora, even if they look good and even if they serve a useful purpose. Personally I think that’s a shame, but that’s the way it is.

That said, I wouldn’t discourage people from wearing whatever they want to if they feel comfortable doing so, and certainly wouldn’t criticise them.

Ian A

Well most people walking around the city are either wearing hiking gear with wooly “Compo” style hats or the obligatory grey “gym jam” joggers with a baseball cap if a hat is worn at all or if they even bother bringing an Umbrella out with them but this does not necessarily make them “modern”.

I may like to wear a sheepskin coat in winter for its protective qualities from rain wind and damp but this does not mean I have to adopt the characteristics of the creature this coat is made from.

I get the point that most menswear in the “modern” post Brummell age comes from military wear but this does not mean that we all must fearfully wear our clothes only in reference to what other men are wearing. I’m not suggesting we powder our faces and adorn wigs and other pre Brummell garb. But taking practicality, style and taste into account the wearing of Bakers boy caps and Fedoras/trilbys is not anachronistic as it is a tried and proven hat to wear in the modern age with an Overcoat in a city/town environment without mountains or a sport track as part of the immediate journey of a man.

does form follow function?

The shape of a hat – fedora versus bowler – seems to me a preference of aesthetics.
Bowler may be preferred again later. I don’t imagine bowler protects less from Mother Nature
than fedora except wide brim might reduce sunlight?

Naked Neck

I’ve just discovered what at first I failed to notice at all despite its itemization and what corresponds to a recent impulse:
your knotted neckerchief! But wispy cashmere however light must be for winter cold, and the price is multiple what that A&S Clifford shop offers at £45 up. Please do an article on this clothing article!

Naked Neck & Thick Skull

PS: I believe I missed your knotted neckerchief because you added photographs later, and I am enthused by the geometric indications – this could be very a very helpful didactic aid for many of your verbal explanations.


I categorised myself as someone who can’t wear a hat, but realised a few years ago that the problem is essentially just that I have a small head and shops do not tend to stock hats in the right size for me.

As testified by some previous comments, flat caps remain relatively popular and I regularly see people of all descriptions wearing them. However, they seem to break all of the principles you outlined (especially height of crown)! Why is this?


Bravo for marching against the headwinds blowing hats (at least with formalwear) increasingly out of fashion.

For most occasions (esp., again with formalwear), hats (esp. brimmed ones) decorate with minimal function. So even once you dodge the costumey trap, you’re held to a high aesthetic standard in order to justify the addition.

And those standards can be difficult to meet. For instance, heavier folks would struggle to follow the (spot on) proportionality principles you point out. If you’ve a triangle-shaped head, with cheeks and jaw more prominent than the forehead, then brimmed hats are essentially out (the crown can rise straight or taper but never flare). Color and material coordination must follow the same principles as those for the rest of the outfit, maintaining harmony in hue, saturation, value, formality, urbaness/countriness, etc.

On top of that you have to think about where to put your hat so it’s not crushed, the politesse of its removal, how to revive your hairstyle…

Just wear a knit cap and be done with it.


Is there a bespoke hatmaker in London?


Congratulations on this article. I’m not based in London but have heard that in the UK’s capital both brimmed hats and flat caps are slowly becoming more frequently worn.
I strongly agree with Ian A. If a hat is worn for practical reasons (against cold, rain or sun) there is no possible reason for arguing against its wearing. So a straw or panama hat in sunshine, or a fedora/trilby worn with an overcoat or raincoat, is much easier to justify than wearing a hat for stylistic reasons. “Suit-and-fedora” is definitely not for me, but (as SB hints), wearing an overcoat or raincoat without headgear looks incomplete to me.


As I get older and less sensitive to how strangers may or may not agree with my ensemble-I have really started to love wearing dress hats and just dressing smart in general… do we really need a special occasion to look and feel great?


For example, if asked “Why the hat?” do I need to explain myself?

I’m a redhead I sunburn easy, or my eyes are over-sensitive when I am outside (happened in the Marine Corps during high altitude training in the snow), or my Dad just passed away due to melanoma and I have that same fair skin…

So ridiculous. How about “I give myself permission!”

Cyril L. Lonsdale

Dear Simon,

You said in a comment : “Avoid black, for instance, and go for charcoal instead (too harsh) and rather like shoes, you should generally avoid navy in favour of charcoal or brown.”
Why shall we have to forget the navy colour for a Fedora ? I saw also that recommendation in a book from James Darwen, 1990, “Le chic anglais”, but this recommendation is very rare. Best regards. Cyril


hi simon
i need more help in order to choose the right hat for me iam 176cm tall i have around full face and grey hair . iike fedora or panama hat and also bakerboy hat for winter what you advice me
thank you


My word, that is one beautiful hat! Which of his styles was it based on? – I need to start saving up for one after I get my Panama from Brent Black.


I had the perfect fedora in 1980, great large crown to match my massive cranium, large brim, no need for an umbrella. Then the stupid Indiana Jones movies hit the silver screen. He stole my hat and I looked like every other jag off Indy wannabes. I was forced to retire my trusted friend.


I’m 6 foot (183 cm) tall and weigh 170 pounds (77kg). With a somewhat oval/square face I want to get a hat that has a 4.5 inch crown and three inch brim. Is that something that would be working acceptable proportions?


Thank you, Mr. Crompton for replying to me. I know you are a busy man and I appreciate your input!


Hi Simon,
I see that your Fedoras all have raw edge. Am I right? If yes, do you consider bounded edge more formal than raw, or you have other reasons to avoid it?



Does this overcoat now hit around the bottom of your knee cap?


Hi Simon, whom would you say are the world’s highest quality hat makers?


Simon, do you (or anyone else on this blog) have experience with Optimo’s collapsible line of hats (the “Mundo” line)? Is the quality similar to Optimo’s normal hats?


Thanks. I’ve been looking for a good quality rollable fedora and a rollable panama. I rarely wear my hats due to the practicalities. Back when hats were ubiquitous, restaurants, bars, theaters, etc. all offered hat checks, but needless to say, that’s no longer the case. And taking a flight with a hat is also highly impracticable. Hat boxes take up too much room, keeping a hat in your lap on a long flight is not realistic, and putting it in the overhead compartment is a risky proposition.
How do you manage these practicalities when you wear a hat? The people I know who wear them regularly live in the city and wear then when they walk to work, so storage is not an issue.

Tony H

Hello, Simon

I’ve returned to this very useful article five years after it was written to ask: where would you go in London to try on a range of hats to get a feel for which ‘last’ suits?

I’m on a work trip there in a few days and probably have time for one decent drop in to a shop.

I’m in the hunt for a summer hat, rather than a winter one, if that narrows things down.


when i was last in, Anderson and Sheppard have a couple of nice summer hats – better value than Lock also.

Tony H

Thank you, both!