I'm not crazy about men in hats unless it's casual (otherwise seems pretentious) and for that, I would go with the the outback styled Indiana Jones type hat, in leather. Those are cool, only because a beautiful leather product can carry its own.
Here's a version that seems too cheap to look good. I am assuming a nice leather hat is much like a women's handbag, you get what you pay for although deals are out there.
From what I have gleaned in men's hats, and not posted here, in the $300 range.

Here is a link that might be useful: This type of hat.

When I was in the antique/collectibles business, I could sell every Panama hat I got my hands on. These still remain my favorite. I still use one for gardening, and will them often in the spring and summer. I have a vintage straw hat collection in my basement I haven't seen in a while.

Here is a link that might be useful: Panama Hats

Nice panama hats too! Dh has several he wears while gardening.
I like looking at these leather hats...here's another one I like. Maybe they don't have to be expensive to look good.

Here is a link that might be useful: hat

Bumblebeez, my (one and only) hat is sort of an Indiana Jones hat, but in waxed cotton. I don't think it started life with the cowboy-style upturned side brims, I recall it being more Panama-like, without the crushing and staining. It's no longer suitable for anything but an outdoor role.

Hmmmm. In my life lots of men wear hats, mostly those baseball type hats with feed company logos though, it's the farmer thing, LOL.

I actually really like hats and have a couple which I seldom wear. When I was much younger, a million years ago in another life, I did competitive riding. I had a lovely pink cowboy hat. (grin) White jeans and pink hat are flashy enough to catch a Judge's attention when you're riding a black horse!

And a lot of men I know wear cowboy hats, boots too...

Annie

I'm partial to the driving cap or newsboy style cap. And trilbys are nice too - a shorter brim fedora. You can Google "trilby" and see that they look cool on females also.

What I don't like is the fashion turban - only those people who wear a turban for religious or cultural reasons should be allowed to wear this type of head covering.

If I can't wear one of those Medieval cones with the veil trailing or a mantilla everyday, I'd settle for a straw bonnet.

Teresa

Here is a link that might be useful: driving cap images

I wear a hat when I am gardening and golfing, for sun protection.

Aftrican Americans are more into hats, especially ladies going to church on Sundays.

dcarch

Annie: Pictures! We want pictures!

That's a good looking hat, John! Worth keeping around but a fresher version would look good too.

I still, after looking at many hats now, stand by the opinion that dressier hats are kinda yucky.
Too old man, or hipster or pretentious yuppie with bald spot.

I think the royal wedding created an interest in hats again. I love hats, although I usually only wear one in the garden. If I need protection from the sun elsewhere, I wear a baseball cap or a visor. Unfortunately, they give me "hat hair," that funny ridge in your hair and then I am stuck wearing it the rest of the day.

My son wears a baseball cap all the time and I am so sick of looking at it.

John, I think your hat is just getting good!

I wore hats quite often in the 80's... haven't worn much in the way of hats in a while. DH thinks I look silly in most of them. He's a baseball cap kinda guy, so I do have a few of those (like the pink one with Wine Diva written in sparkly-beads), but I think I look sillier in them than in the "ladies hats" I used to wear!

I'd love to see more hats out there. Fedora, Panama, Indiana Jones... For myself, I'd love to sport a nice conservative cloche... maybe I'll see if I can knit/felt one... hmmmmmmmm

Here is a link that might be useful: Cloche

I used to wear hats a lot. Now I just wear them for shading my face, and to prevent my hair from flying all around when I walk the dog on wintry days. I need some more for this winter. I wish hats and gloves would come back into fashion. But that would mean getting out of this extreme casual clothing rut the whole world is in. And don't get me started on the grown men in baseball caps phenomenon - especially backwards caps.

I found a picture of the hat wearer referred to in my initial post. Exhibit ''A'' for why ladies should wear hats.

Amish men, and orthodox Jews always wear hats.

dcarch