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How do you wear a hat without looking ridiculous? Hat lovers, please advise.

by Borsalinoreply 3209/09/2014

I honestly think it depends on the size of one's head. If a head is too big, regardless of hat style or fit, you'll look like a watermelon in a particularly nice chapeau.

In a general sense? Like so many things, confidence! Confidence goes a long way.

by Borsalinoreply 104/05/2010

I look stupid in hats, too, OP. My boyfriend does, too. I think some of us just don't have the heads for it.

by Borsalinoreply 204/05/2010

Anyone who wears a hat backwards looks ridiculous. Further, when viewed from the side, it makes their nose look huge.

by Borsalinoreply 304/05/2010

Does anyone...still wear...a HAT?

by Borsalinoreply 404/05/2010

I do, as many in my area. My advice is to place it on your head and simply walk down the street.

by Borsalinoreply 504/05/2010

Confidence is the only answer.

by Borsalinoreply 604/05/2010

I wear hats every day of the year, mostly as a form of sun protection.

I agree with R1. Confidence is key. You have to wear the hat, not let the hat wear you.

A lot of women refuse to wear them, however, because they fuck up their hair. That I can live with. Skin cancer? I can't live with.

by Borsalinoreply 704/05/2010

Depends on the hat. When worn functionally (such as a winter skull caps for warmth, or visors for the sun) they are easy to wear. As an ornament, much harder.

by Borsalinoreply 804/05/2010


by Borsalinoreply 909/09/2013

Big women with big heads wearing huge hats look like walking Cinzano umbrellas.

Imagine a walking Cinzano table umbrella coming at you!


by Borsalinoreply 1009/09/2013

I mourn that men (and women) don't wear hats as standard attire as they did in the 40's, 50's & first half of the 60's.

It was so handsome and elegant.

Today, unfortunately, it's just douchey.

by Borsalinoreply 1109/09/2013

Hat lovers are probably not the right people to ask.

by Borsalinoreply 1209/09/2013

You have to find a hat with the crown and brim size for your head. Some people (mostly with small heads) look great in pork pie hats (or any with a smaller crown and thin brim) that are popular. Men with normal sized or larger heads usually look better in a fedora. The shape of your face can also be a factor when selecting a hat that will look good on you.

If you live near a decent hat store (I know, there aren't many left these days), the guys in there can help you find a hat that will not only look good on you, but will fit properly.

by Borsalinoreply 1309/09/2013

You become my clone.

by Borsalinoreply 1409/09/2013

R11, I agree! Are you a fan of "Mad Men", as I am?

by Borsalinoreply 1509/09/2013

Wearing hats just takes the right attitude, OP

by Borsalinoreply 1609/09/2013

I like wearing hats, but never did until I was in the service, where we had to. I have a lot of hats; baseball caps(several dozen); 2 cowboy hats, the smaller ones, not the ten-gallon ones; one fedora;about a dozen watchcaps/skicaps, most of which I made myself. I like the feeling of something on my head, it's very comforting. I think a hat completes an outfit, even if it's very casual. Some people DO look good in hats, I call it having a good "hat face." FINDING hats that fit properly is difficult, I have a very large head(7 and7/8, but 8 is a better fit) I'd love to find a hatter that would make custom-sized hats for me. Have a few hats I call my "go to hell" hats. If you don't like 'em, you can go to hell! Hee hee.....

by Borsalinoreply 1709/09/2013

Most guys wearing fedoras just shouldn't

by Borsalinoreply 1809/09/2013

Every man needs a bill cap. The secret to looking good in one is finding the right hat and make sure it fits.

by Borsalinoreply 1909/09/2013

I think I can wear most hats (average size head, ears, face) but I don't really care if someone else doesn't like how I look. Their problem, I've got a warm head on a cold day. My bf does NOT suit hats. Even just a casual beanie in winter makes him look like he's going to steal your car and maybe rape you a little bit. He's just got a face that immediately looks criminal / shifty in a hat of any type. Maybe not helped by having black hair and a very heavy growth even within an hour or two of shaving, makes him look slightly thuggish even when wearing a nice suit.

by Borsalinoreply 2009/09/2013

I would love to be able to wear a kicky beret. But alas my head is shaped all wrong.

by Borsalinoreply 2109/09/2013

"Every man needs a bill cap." = INSTANT deal killer/dick wilted.


by Borsalinoreply 2209/09/2013

R19, I'll never wear one. I need something that would cover my years

by Borsalinoreply 2309/09/2013

Derbys are never ridiculous.

by Borsalinoreply 2409/09/2013

My dad wore hats and looked great, mostly a black beret or Homburg. He didn't wear the grey fedora of his younger, slmmer days as he got older and I never knew why. I think I inherited his "hat face," and maybe the feeling that hats are normal.

by Borsalinoreply 2509/09/2013

Don't they make your head all sweaty?

by Borsalinoreply 2609/09/2013

I have a lovely collection of baseball caps, but due to the previously mentioned watermelon head thing, or whatever it is that makes me look stoopid in them, they are not worn. I tend to really like to see guys who can work a baseball cap to good effect. They can hide a multitude of short comings for those dudes, lucky fuckers. I really do enjoy wearing my Elmer Fudd hat in the winter, people tell me I look like their retarded nephew, hell maybe I do.

by Borsalinoreply 2709/09/2013

Bump for a new hat season

by Borsalinoreply 2809/07/2014


by Borsalinoreply 2909/07/2014

So which hats go with which face shapes?

by Borsalinoreply 3009/07/2014


by Borsalinoreply 3109/09/2014

VERY, VERY few guys can wear a beret without looking ridiculous.

by Borsalinoreply 3209/09/2014
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