How To Wear A Trilby


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.



Simon Crompton is a journalist and a style enthusiast living in London, who blogs at He has too many suits.


  1. It’s a myth that you lose most of your body heat through your head. I am a cold-water swimmer and, although I always wear two caps, I can tell that my body loses heat all over, and that I feel it in the chest and back.
    BTW, the New York Times had a piece on this about three years ago.

    Nice stuff about hats. Been wearing them a very long time.

  2. NYT was on heat loss not hats.

  3. Seth is right, you do not loose most of your heat through your head. The idea came about due to a flawed military study from the 1950s.

    That doesn’t mean you don’t need to cover your head, a hat can help in cold weather, but it’s no more important than other cold weather clothing.

    I felt self conscious the first few times I wore hats, but I found the reaction form people was positive. I got more smiles, more compliments, and more friendliness when I wore the hat than when I didn’t. Now I feel weird if I go out without a hat.

  4. I baught a nice pork pie hat last month in London, and I wear it regularly.

    I see some smile around me, but in the same time I can read some glimmer of covetousness in the eyes of these cheerful guys.

    So keep walking………..

  5. I disagree about having to ‘balance’ the hat. It seems a shame to wear something as beautiful and elegant as a Lock & Co. hat with casual clothing.