It’s not easy wearing a hat. You stand out more in a crowd than a man wearing polka-dot knickerbockers or a cape. The hat radically changes a man’s silhouette, probably more than any other item of clothing.

People look at you if you wear a hat. Anyone that is passionate about classic men’s style is probably used to the stares of others. But a (proper) hat draws stares from everyone, everywhere. I bought my first proper hat – a brown-felt trilby from Lock & Co – a couple of weeks ago and am just getting used to these sensations, this attention.

The comments on that previous post included: “I have been a daily hat wearer for years. While I do get the occasional odd glance while wearing a hat, I mainly get compliments” and also “wearing a hat makes you look like a dope, especially if the hat is a very fine one.” I can completely understand why men are passionate about hats in both directions.

I think the reason is that everyone knows hats are incredibly practical, but they don’t feel comfortable wearing one. And I can’t help feeling that perhaps they resent that. Or they resent that their head gets cold and they feel silly in a beanie. And flat caps look odd, or over trendy.

A hat keeps you warm. It’s an overused fact, but a fact nonetheless, that most of your body heat escapes through your head. When you get older, losing your hair, many years from now (as the Beatles put it) you need something to cover your head in cold weather. It’s necessary.

And a hat keeps you dry. Remember those close ups of Humphrey Bogart, standing in the rain on a street corner, watching the house opposite? The rain was pelting down on his hat and trench coat. But he wasn’t getting wet. It’s an oddly liberating experience when you first where a proper hat in the rain, and everyone around you is either clashing umbrellas or scampering for cover.

If you just don’t like hats, fine. But trust me, if you have even the sneakiest suspicion that you might like one, try it a few times and you won’t want to turn back. Sure, you’ll feel self-conscious, but that’s the case with wearing anything new. I used to feel self-conscious wearing a pocket handkerchief. Now I get odd looks if I’m not wearing one.

Some hat enthusiasts will disagree with me, but I think a hat is also an unusual enough accessory to need balance elsewhere. I won’t wear my hat with a double-breasted suit, tie and briefcase. Because to me that is straying almost into costume – or a lack of individuality. I think my hat looks best with casual trousers, a blazer and open-necked shirt. Perhaps a raincoat on top. In the same way I wouldn’t wear a tie, pocket handkerchief, tie clip and boutonniere to work, no matter how good it might look. It’s a question of balance and personal taste.

Finally, for those that requested it, there are shots here of my hat with its box, and a photo of how it looks rolled up for travel.

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Sartorial Vancouver

How to wear a trilby? Put it on and forget about it. You have to wear the hat, do not let it wear you.

The state of dress is at the point where in some circles men get stares for wearing collared shirts, let alone ties and suits. I trust you get the looks because you look good. Be proud of your presentation and style.

Coşkun Hürsel

I do not come from a western society, so this may be a dumb question: Do you take your hat off while indoors or while you board a bus? I have come across some people, who consider it rude to wear hats indoors, while others say “keep it on at all times.”

Reatha Brunjes

I know this comment is years late but generally men take their hat of indoors and women keep theirs on.

Allen Gray

When entering a retail store such as a grocery store, should you remove your hat or continue to wear it?


“It’s an oddly liberating experience when you first where a proper hat in the rain…”

This should most definitely read “…first wear a proper hat…”


Congratulations! I told you you’d get used to it! I find a hat (I prefer fedoras) and a raincoat are often all I need in the rain, and when it’s too windy for an umbrella, it’s the only way to go.

And yes, you take your hat or cap–fedora, trilby, pork pie, baseball, flat, or otherwise–off indoors, though not necessarily in “public” spaces, like hotel lobbies and elevators (a practical rule–where are you going to put it?). You may also keep your hat on if you eat at the counter, but must take it off if you eat at a table.


Fuck that. Mine stays on. I don’t care whwt anyone thinks.

Arctic Penguin

Simon, what’s your understanding of the portability of similarly constructed hats? I’ve got one constructed of green felt that seems very similar to yours, though I have no idea of how to judge its ability of being rolled up. As it was received as a gift, I likewise have nothing in the way of documentation accompanying it, so while I can asses its quality, which is good, I know neither how to care for it nor if I can roll it up as you can yours.

Edu Coelho

I like the pictures. But now it’s just missing a photo of you wearing your hat.

Laurence John

‘flat caps look odd’ isn’t a very useful observation. they’re no odder than a trilby, and probably more versatile.


In general, unlined felt hats may be rolled or flattened for travel. To remove any unwanted creases or otherwise reshape it, put a kettle on the stove then steam your hat. It can then be shaped to the desired form.

You should probably wear rubber gloves when you do this–steam is very hot.


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I strongly dislike the wearing of an open-necked shirt with a blazer (or suit, or sports jacket).
A raincoat looks good worn with a trilby; indeed, those who wish to start wearing hats would find it easer at this season when an overcoat or raincoat is usually worn. Apart from a flat cap with a tweed jacket, or a summer Panama,
a hat worn without an outer coat looks somewhat affected to me


I feel obligated to point out that the common fact that most of your head escapes from your head isnt exactly true, read this from the QI website:

THE MYTH: You lose most of your heat through your head, so the most important piece of outdoor clothing is a hat.

THE “TRUTH”: Everyone knows this. Look at an outdoorsy website and you will be told it again, just in case you’ve forgotten it. But apparently, it’s not true. Anything from 5% to 55% of a body’s heat loss can be from the bonce area, depending on various factors, including how much hair you’ve got. But there’s nothing special about the head: any exposed body bit will lose heat, and how much will depend to a great extent on how big it is (flashers be warned). Logically, if this myth were true, wearing a hat but no trousers would keep you warmer than wearing trousers but no hat: it won’t. (Flashers be doubly warned). Hypothermia expert Dr Daniel I. Sessler, of the University of Louisville medical school, blames the belief on military experiments, using Arctic survival suits, conducted half a century ago. The suits did not cover the subjects’ heads, so of course most heat loss was from the top. Someone wearing just a swimsuit in cold conditions, says Dr Sessler, would lose only about 10% of their heat via their heads.

pretty picky point but logically true nonetheless

Rob J

I have been wearing a hat since 1986, at a time
when it was very unusual. Nevertheless, I was always given a compliment.

Now that the marvellous “Mad Men” series has
brought back the classic menswear look circa 1960, when wearing a hat was the norm, it doesn’t seem so odd. I recently found a Homburg in mint condition which attracted a few admiring glances from the opposite sex.

With the right attire, you can truly stand out from the crowd. And girls love it !


Just returned to a trilby after being hatless for 20 years,cap doesn’t count,Love my trilby,Dunn& Co bought used on EBay but in excellent condition.Wore it in our local market town yesterday & felt very English,which I am,I seemed to be the only man wearing a trilby but who cares

facebook_Dek Smith.10204276626916085

I’ve thought of having hats for years but never did. Now i’m almost 60 but young with it I decided I want a hat so 6 flat caps three cheep and nasty trilbys and two mega expensive trilbys Guess what i wear the expensive ones with pride. Ok look a dick head but who gives a dam I feel good


Hi Simon, I have a question about hats in general in relation to style vs function. I have a brown felt fedora, a flat tweed cap (John Hanly), and too many beanies. I live in New York, so the caps and the fedora aren’t great below 40 degrees F / 4-ish Celsius, as the ears start to suffer the cold. In the northern USA and Canada, it’s an important consideration. (BTW, one of my beanies is more “tailored”, which is nice, but doesn’t offer ear coverage). I also have a vintage beaver sides fur hat and an astrakhan hat (imitation fur), both picked up very cheap, they cover the ears but just don’t seem to suit me. Any ideas? What do you think of (discreet) ear muffs with a fedora? Possibly a bit silly looking, but if it worked, it would be great. Maybe the Filson Insulated Packer (tin cloth, with ear flaps) is an option, but the look isn’t quite fedora, more forestry / boy scout. Anyway, I’d appreciate your thoughts. Thanks so much, David


Simon, you’re right. I gave the beaver hat a try today (“feels like 25 Fahrenheit”) and it doesn’t look bad, and – it is very warm, so I think it’ll be a go-to for the colder days. Thanks again!


Hi Simon,

Commenting on an ancient post because I recently took the plunge and bought my first trilby! I’m used to wearing a decent flat cap when out walking etc. but this was my first formal hat.

Less than a month on I now feel very comfortable in it and much less conspicuous than I did to start with. I went out to work without it yesterday and immediately missed it – I felt as if people might turn and look at “the man who’s forgotten his hat”.

BUT I realised today that if I wear it with a suit and tie but without a coat I feel much more self-conscious, and as if I’m in costume. I suspect this is partly because there’s much less bulk lower down the body to balance it, and partly because if it’s not cold enough out to wear a coat then you’re evidently not wearing your hat to keep warm (it’s a pretty mild day), so the practicality factor vanishes and the hat is magically transformed into an affectation. The difference in my self-consciousness levels was like night and day.


“wearing a hat makes you look like a dope” Said all lazy men who wear stupid looking baseball caps that are essentially billboards on their head.