Hats with coats: A sliding scale

Friday, March 19th 2021
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I’m often asked which hats work best with different types of coat. In fact, it often comes up at this time of year - I guess when unexpected showers are more of a hazard.

The sliding scale of formality with hats is pretty intuitive: a fedora is smarter than a cap, which is smarter than a beanie.  But, some of them do cover a greater part of that scale than others. 

A good, neat watch cap for example, can work with everything from a navy overcoat to a blouson. Whereas a brimmed hat is more limited. 

Here then is my breakdown of the types of hat and what I find they work best with, illustrated with examples from previous articles. Let me know if you don’t recognise any of the images, and want to know where the various pieces come from. 

Brimmed hats

The smartest hat is always going to be brimmed headwear like a fedora, and it’s smartest in dark colours like charcoal (above). 

Generally a hat becomes more casual the smaller the brim (at some point becoming more of a trilby) and after charcoal the smartest colour is usually dark brown, with mid-brown, green and other lighter colours being more casual. 

A brimmed hat is not an easy thing to wear these days, as they stand out so much. But it’s always easiest when they’re eminently practical - with an overcoat, in the rain. When everyone else is trying to avoid clashing umbrellas, and you’re perfectly dry and well as perhaps looking rather good. 

Fedoras work best with overcoats and with raincoats, for that reason. They can look good with casual coats or even just a jacket (a friend regularly wears his with a field jacket).

But it is always more of a look, and you’re more likely to want something smaller, perhaps even worn with the brim up. 

Casual brimmed hats

The only alternative to the classic hat-and-coat I wear is more casual colours or materials of fedora, with more casual overcoats. 

Above, for example, I’m wearing my taupe-coloured overcoat from Ciardi, with a hat from Optimo in a colour called silver belly, which you find most often in Western-style hats.

Indeed, even with the brim snapped down at the front, this has something of a Western look - due to its high curl at the sides. 

I find these paler hat colours often look better with my more casual styles of overcoat. Another example is my tweed ulster from Liverano, with a Wellema ‘pecan’ coloured hat -  which I’ve included an image of at the bottom of this article.

Still, a brimmed hat still has fairly narrow use for most everyday guys, who won’t want to look that unusual. 

Flat caps

I’m using the term ‘flat cap’ here to encompass everything from a close-fitting cashmere to voluminous baker-boy. Basically anything flat with a peak at the front. 

I find this category rather versatile, as long as the style of cap is right. I have two suede caps from Lock & Co, for example, (the Tremelo model, above) and they work with most overcoats as well as a pea coat or waxed jacket.

The reason they do, I think, is they're fairly close-fitting  - not flopping over to one side, covering an ear - and are in suede rather than hairy tweed. A coarser material and bigger shape would be much more casual. 

The biggest issue with flat caps, as with many hats, is their associations. Some people just think a flat cap makes you look like a wide boy or a dustbin man.

To them, I would suggest they check out how John Simons or others from his era wear the cap. To create some better associations. 

Beanies / watch caps

This is by far the most versatile of hats. In fact, its biggest danger is making people lazy, encouraging them to wear nothing else. 

A neat, dark watch cap can look surprisingly smart. I often find myself wearing a dark-navy one with even my smartest overcoats. It does have to be neat though - not too thick, not coming down to back of the neck. (Which was, of course, the spur for designing our own, the PS Watch Cap.)  

And yet a watch cap also works with a field jacket, with a blouson, with a horsehide jacket (see below). It goes with everything. For that reason I think everyone should have two or three - perhaps a navy and grey, then one more unusual like cream or red. 

However, don’t let this put you off wearing other styles of hat. When the rain is falling, when you’re not rushing out of the house, or when you just feel like something different, try a fedora or a flat cap. 

Baseball caps

Baseball caps have seen a surge in popularity recently, partly because their fashionability also makes them more versatile. 

If you liked them, a baseball cap was always suitable for more casual coats and jackets, and of course just a shirt or knitwear. But it’s also become fashionable to wear them with tailored jackets or overcoats, partly because it adds a sporty element to otherwise sharp clothing. 

I’m always sceptical about such trends, but I rather like a baseball cap worn in this manner. It’s a very easy form of high/low dressing, and one that is easy to play around with, or switch during the day (or a trip). 

As I discussed in our article on high/low dressing, it’s easier to do this with outerwear and accessories, because they are so easy to change yet have an immediate impact. 

Still, I wouldn’t wear my beloved Berkeley cap with a really smart overcoat or double-breasted suit. That’s too much for me. The smartest I'd wear it is with a polo coat (below) and more standard is with a waxed jacket (above). And everything more casual than that

That’s my hat/coat sliding scale of formality. For those that like these sliding scales, others include: 

Below are a few more coat/hat combinations, to add examples to those above. As mentioned, let me know if you’re a new reader and don’t recognise the outfits: leave a comment and I’ll direct you to the details. 

Wellema taupe-colored hat with tweed coat
Beret with donegal raglan coat
Watch cap with trench coat
Watch cap with horsehide jacket
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Peter

Possibly you intended to hyperlink the other sliding scales of formality pieces?

Anonymous

I think you have missed a trick on formality. What about the blocking? You can wear an unblocked hat with a rim (rare for men I know) but also a hat can be blocked with a lot more structure. A fedora with a rigid crown and brim is a LOT more formal than, say, the rollable voyager from Lock.

JJ

That Optimo western Silverbelly looks gorgeous! Is it a tear drop or a center crease crown? Would be great to know more about it / the process that led you to it. Thanks.

JJ

Thanks, great!

I have an Optimo in the Silverbelly felt but in a traditional center crease fedora, which I really love. Out of curiosity, have you noticed a difference between the Silverbelly felt and the felt on your first Optimo hat, which I understand is not the “heirloom” quality, as the Silverbelly is?

Also, I assume this was a bespoke commission but did you base it on any of Optimo’s standard models?

Your hat is that rarest of birds – something distinctive but in a very subtle way. Really elegant but also casual. Well done!

JJ

Noted, thanks. Would appreciate it if you could share Graham’s input when available.

JJ

Thank you Simon, this is very helpful. Much appreciated.

Peter Hall

Yes to hats!

I have a Brisbane fedora, which is very sharp, a little more angular and very smart. PS exposure convinced me to invest in a couple of beanies, and I agree with your comments. Would there be enough interest to justify a feature on a uk hat maker ? We should value our crafts people.

Paul

I’d be interested in your take on “purely functional” hats, such as those made by Tilley. They’re not trying to be particularly stylish, and many of their designs I wouldn’t be seen dead in; but something like their tweed winter hat has a shape rather like a less-formal fedora. I have one in a darkish grey herringbone tweed which seems to work pretty well with, e.g. the PS Donegal coat. I doubt I would push it with anything more formal though. Does this kind of thing live in a completely separate “space” or is there a place for them in your formality scale?

Fatih

I love that suede cap. It looks lovely worn with that navy coat. What seasons can you wear it without it getting too hot?

Alex

I love proper hats, but when combining with a long coat (especially a trench coat) always feel a little bit as if I’m indulging in Humphrey Bogart cosplay.

zo

As nice as the top two hats look, the only brimmed hat I can get myself to wear is a bucket hat. Anything smarter I find quite anachronistic and, imo, it imparts a ‘look’. I used to like berets too but now I feel the same about them.

3NMa

I personally think hats look and feel really good as well as serve a purpose, and you wear them just like i think looks the best.

What about the ushanka? In some eastern european countries they are sometimes combined with more formal clothing. And they’re plenty warm, maybe too warm for London now that I come to think of it.

All the best
3NMa

WES WP

Simon:
Simply put…you make these hats work, and you “work” these hats (in a runway sense).

I really don’t like hats (and don’t own many) because I simply cannot pull them off (pun intended). I’m not overweight, but I just feel “fat” in a hat (that hats make me look dumpy).

But – for you – many of these are splendid pairings, and they flatter you tremendously.

Wes

WES WP

I’m not done with hats. I have a renewed sense of optimism. And I haven’t tried everything — just a handful of things. I also have a massive head. You can’t tell by looking at me, casually, with the naked eye — but I am an XXL hat size. Perhaps that’s part of the problem: most hats just don’t fit me. Anyway —- I’ll keep an open “mind.” (please excuse these Dragons-Den -level cringey puns)

Scott

I really like that suede cap from Locke. Of course the main issue with any kind of hat or cap is the dreaded hat hair look that occurs. I suppose this is just something that men have to deal with when wearing hats.

Flaubertine

Chapeau!

Justin

Another interesting article, thank you. All of the hats that you discussed in this article are much more geared towards cold weather, winter, and rain.
Summer hats seem more versatile to me, for some reason. I feel like I can wear my panama hat with a much greater diversity of formality. It seems to work well with the most formal summer clothes I own down to very casual outfits.
What are your thoughts on where Panama hats fit into this scale?

Tom

A bit of a weird one but does anyone know any makers of bespoke baseball caps? I have an extremely large head and have never found any cap which really fits.

Charles

Hi Tom
Ebbets Field Flannels has very nice hats in various sizes. Made in the USA. You could try them?

Tony H

Hi Tom – I went hunting for some last year, and the only ones I could find were on Etsy. I didn’t give them a go, but if you do I’d be keen to know how they turn out.

Andrew Poupart

I agree with your appreciation for Optimo. My Optimos have sidelined my hats from all other makers now. Graham is currently making me an Optimo version of a Stetson Stratoliner, which I envision as a summer alternative to various Panamas. Everyone at Optimo is so helpful and knowledgable, plus their retail space is one of the most remarkable stores I’ve ever been in—a kind of temple of hats!

I never wear watch caps, beanies, or tweed caps. I think, for winter wear, three Fedoras are sufficient, one in mid- to dark-grey, one in navy or slightly lighter (mine is Optimo’s Blue Pearl felt), and one in brown. The grey and navy cover the more formal work, the brown works with tweeds, greens, and so on. I tend to pair a navy hat with a navy overcoat. But with other colors of overcoat, I tend to compliment the suit (or trousers, really) that I’m wearing. So, with my orange overcoat (I can hear you shuddering all the way from California, Simon!) grey or navy work equally well. And I think the grey works well with a camel-color coat, such as The Anthology polo. Otherwise, the brown compliments the camel color nicely.

Regarding wearing a fedora with a trench coat and looking like Humphrey Bogart? Well, ain’t nothing wrong with that, although I tend to think I always look like me! Incidentally, in all the years I have worn hats, no one has ever said anything derogatory, at least to my face. The comments I get are always complimentary. As for whether or not someone can “pull off” a hat, it’s simple: you can if you think you can. But, as with many things, it is worth investing the time to understand make and fit.

Andrew Poupart

And for some reason, my name got cut off. Ah, well.

Adam

I got a nice dark green toque (uhh… watch cap) from Drake’s this year and it’s turned out to be a pretty good colour. Goes with everything, as you say.

How practical do you find a suede flat cap in wet weather? A tweed flat cap would be more practical than a knit wool hat when there’s rain coming down but I’m not sure I can pull it off.

Hugo

I do wish I would feel comfortable enough to wear a fedora. Perhaps one day. Until then though, I recall you doing a shoot with a suede baseball cap at some point. I quite like that, and have been trying to find one without and logos or other disturbances, but unsuccessfully unfortunately.

Mark

The first time I put on a fedora I felt that everyone was staring, that it wasn’t quite right. Whilst I know the reality is that no one really is staring, in my experience it took about 15 or so times until I no longer had that sensation.

It was only after that I probably started to relax and ‘wear’ it. Now it would seem a bit odd to me not wearing a hat on a cold day and when people do comment, I only get compliments.

My point is I think everyone can rock a hat. All one needs to do is just to get past those first few awkward days and then start to relax and wear and enjoy it.

If nothing else, your head will be warmer and ultimately is not the main reason we dress for comfort?

Hristo (STEMESO Socks)

I like fedoras but it is so difficult to wear one nowadays without looking like somebody heading towards a carneval party.
The reason is, that people wear them so seldom nowadays (I am talking about Germany) that a fedora immediatelly grabs the attention and looks strange.

Romaneseuntdomus

While I completely agree with you that Germany is mostly a sartorial dystopia, especially when it comes to hats, your first sentence seems to adopt the view of bareheaded common people. If you wear your fedora(s) regularly and with confidence, people will just get used to it. I went through this experience when I started wearing the most quintessentially of English hat, my Lock & Co. bowler, in a rural town in Germany.

D. T.

I think a Homburg has its place here too, but is even more of a look! (Black tie ala commissioner Gordon in Batman 1989, not to mention the topper). The one thing I find is that brimmed hats blow off easily in inclement weather which lessens their practicality. As to makers, I agree with another comment and find that my Optimo hats have consigned hats my from other makers to the second best shelf.

Andrew Poupart

I agree with Simon: I’ve never had a hat blow off in the wind. It’s felt like that might happen, once or twice, but if you snug it down it should stay put.

Alexander McShane

Simon, first of great article. It’s interesting to see the different looks of the headwear that can change the entire feel of an outfit. The image’s at the end really show that point off as even a ballcap can look suitable with an overcoat.

I have been looking at fedora’s for a while and really am taken with getting one, but you have made me interested in the Watch Cap, any suggestions on where to get one?

Alan

Good article as always and some great hats, particularly the silverbelly Optimo. I find you can wear fedoras without an overcoat but it is more of a “look” and one you have to be very comfortable with to carry off without looking like you are wearing a costume. I have been wearing fedoras since I was 17 and I used to get a lot of stupid and sometimes downright aggressive comments back then. However now (over 10 years later) I never get stupid comments, whether I am wearing my fedora with a field coat, overcoat, sport coat or suit. I attribute that partly to being more confident in it and partly to wearing better fitting, more refined clothes.

If you look at old black and white photos you see people wearing fedoras with literally everything, right down to overalls. I’m not suggesting anyone goes that far but it does suggest that a fedora does not have to be limited to being worn with overcoats if you have the confidence and style to carry it off.

Daniel Schmergel

Lovely piece, Simon. Are there any other makers you like for flat caps? I have a number of caps from Lock—including the suede, the purchase of which was inspired by you—as well as numerous iterations from Borsalino, the EU Stetson line and a local maker out of Brooklyn by the name of Kai D. (who you might want to check out), but I’m always on the lookout for other options, as my hunger for flat caps is nigh insatiable.

Daniel Schmergel

The suede ones are great, but I wear one nearly every day–cashmere and wool in the fall/winter and linen, cotton or raw silk in the warmer months–so I’m always seeking new options. Thanks for the reply though!

Damian

Hi Simon. It would be interesting to have your thoughts on a Panama; when to wear (and when not), what outfits and levels of formality e.g. shorts? Thanks

Nick

G’day all,

Being Australian, all our family got hats. Originally we bought them for an actual practical purpose, the Sun but it becomes part of the coastal style. For those who are not aware, we have an iconic Oz brand, Akubra. It is made in Australia and top quality. Hugh Jackson and Nicole Kidman wore Akubra in Australia movie.

michael powell

I wear hats for cool/cold weather (late October until early April in Chicago). I wear only Greek fisherman’s caps. The black cap works with a charcoal overcoat, a duffle coat, or a peacoat. I wear the Greek caps because when I was young, Jackie Stewart and John Lennon wore them; and I thought they were cool guys. (It seems Jackie started wearing one because John wore them. Who knew?)

Tony H

Hi Simon – this is a bit of a tangent, but when you mentioned the functionality of hats with raincoats it got me thinking: what raincoats do you reach for these days?

I’m kind of in the hunt for one, and a quick search tells me it’s been a long time since one featured on PS.

Robert

Hey Simon-
Great post. The Optimo with Ciardi overcoat is a showstopper. In the original review the fabric appeared brown, but here it reads as a lighter beautiful taupe. The beret with the Donegal is an ode to 1940’s glam and is fabulous. Yes to your Cal baseball cap countryside traipsing through the moors. I think they are overdone in city centers unless you’re in grammar school but I’m 20 years your senior and might need to loosen up.

Rob

Enjoyed the article. Totally agree with your comment (elsewhere in respect of one of your Optimo hats) about how important the band is to the look/feel of a hat. I had a custom beaver fedora made in San Francisco, but have gone off the band and therefore the hat. It’s impractical to send it back to have it changed. Can anyone suggest someone in London who may be able to change it? I know many places will only work on their ‘own hats’. Thanks.

Chancellor

I’m looking to buy a first hat (probably through Leon Drexler since I don’t live too far away from him), and wondering about your advice on colour and style.

I want it to provide warmth during the cold days of fall and spring (suspect no smart hat will be warm enough in the middle of winter). I’d like it to be formal enough to be worn with a dark formal overcoat with suits, but if possible, also with a dark peacoat with knitwear and the PS trench coat. Hopefully that isn’t too wide a range for versatility.

Would a medium grey or charcoal be a good colour? I don’t know enough about styles, so advice there is particularly welcome.

OP

A good post is one you’ve been waiting for. A great post is one you’ve been didn’t know you were waiting for.

Monsieur Khartoum

Hello Simon, i am big fan of wearing Baseball Caps with tailoring, could you please tell me where i can find your Berkely cap? Thank you

Martins

Unfortunately I don’t think hats can work for me due to head size… Think 66cm coconut on a 44 shoulder size… 🙂 Also…
Beanies is the only thing i can wear. (I would like yours but beanie for me needs to be able to cover ears!)
Baseball caps I really don’t like.
Flat caps, maybe, and that’s a big maybe! Just no one is making my size.
I was really looking at Locke suede one, but even mto they can’t make my size in suede! Any other material, just one size down and stretch it. (Almost double rtw price). If you know someone doing a 66cm size, do let me know please!
Anything brimmed just makes my head even bigger, while narrowing shoulders…

Martins

actually thank you! I tried on my beanie like you wear, and surprisingly it’s ok! now just a question remains, if yours would not be too small for me!

Martins

I know circumference should stretch, but how about height? For 66cm head I wouldn’t want it to look like Jewish cap…

Kenny

“Some people just think a flat cap makes you look like a wide boy or a dustbin man. To them, I would suggest they check out how John Simons or others from his era wear the cap. To create some better associations. ”

The association with dustbin men is just an outdated metropolitan cliche. Flat caps have become more popular in recent years, partly due to the success and fashion influence of “Peaky Blinders”. In the countryside, they are always in fashion and worn by many such as farm workers, the landed gentry and their shooting guests.

Flat caps are very popular in Spain where they are worn by the locals when they go out to tapas bars in the evening. I bought a checked cotton cap, made in Italy, from a specialist hat shop in Sevilla for only 11 Euros. The quality of the huge range of tweed caps, Panamas, trilbies and fedoras was as good as Lock’s but a tenth of the price. I can’t wait to go back.

Michael
Chris

Simon, What are your thoughts on a brimmed hat with a Barbour? I have an older Sage Border model that I often wear over suits or trouser/sport coat combinations and have wondered about how it might work with a darker green fedora.

Michael Ryan

Simon, thanks for the great article and introduction to Locke & Co. which I coincidentally just bought a hat brush from (through Taobao here in Shanghai) without really having heard of them before. I will order a new Panama hat from them this summer. I’ve been buying from Belfry Bagota in the US with reasonable success but the postage to China about 5 times any delivery from the UK and has always given me pause. (I get a lot of deliveries from Herring, Drakes and Charles Tyrwhitt)

Of all the ubiquitous styles I can’t pull off, it’s baseball caps. My daughter says I look like the building handyman when I wear one (we don’t actually have one so she’s afraid people will ask me to fix things). I have been wearing a Panama hat for years and bought my first felt fedora this winter. It works great for me especially in the rain. As a tall white guy I get looks no matter what I wear so I’m not remotely concerned about standing out, I’m immune to it after 17 years.

Boris

I find the beret to be in quite a peculiar spot personally:
I either wear them with more formal outfits, like a two piece navy suit, or anything with a tie
Or I do them like the French do with the more casual styles, such as T-shirt and light jeans.
I can’t seem to fit them into the middle section of formality, just shirts and trousers, or with a shirt jacket, it feels a bit off.
Intrigued to hear your thoughts on the beret, phenomenal piece as always.

Nico

In this time and age of faltering at wearing a tie or pocket square; do you feel “relevant” wearing a fedora with an overcoat? What about spectators then?

Nico

Fedoras have got as anachronistic as spectators in my opinion, Simon. A shame maybe since they can be practical, as much as with spectators since they are beautiful, at least to my eyes. Differing sensibilities, I guess.

MP

I’d be grateful for some advice, Simon.
Do you think that a fedora would work with less formal outfits, such as with a PS Wax Walker(which, as an aside, is a fantastic item!). If so, what colour would you go for – perhaps brown, or navy?
Do you think wearing one with an M65 or French F1 army jacket would be pushing it too far?
Many thanks.

MP

Thanks, Simon. Your guidance is much appreciated.