Advice regarding any Mens's hats you can wear that don't look silly?

Sombreros, straw boaters, Deerstalker (flaps up), aviator caps, Irish flat caps. I don’t know what Hipster means.

@gailcalled From Wikipedia:

“hipsterism fetishizes the authentic elements of all of the “fringe movements of the postwar era—beat, hippie, punk, even grunge,”

I am looking for a simple hat that would look fine in business causal situations, and not look like I think of myself as a cowboy, or trying for a purposeful affectation.

I was around for that era and I don’t remember the Beats or hippies ever wearing hats. Headbands, yes.

There are only so many headcovers available for males. Fedoras, the boring felt hats that my father ( a traditional and conservative businessman) wore in the late 1940’s and early 1950’s and the Irish and Scottish caps worn across the pond.

Here’s Humphrey Bogart…he looked better than my father.

A guy I worked with wore a cap like the one in the link. He was completely bald and I think he looked good in it. I think it’s really dependent on what you are comfortable with wearing.

I really think Aussie leather hats are very flattering and chic looking on almost anyone.

Wearing a baseball cap won’t make you a hipster.
Unless you wear it whilst pushing a vintage bike that you never actually ride to Starbucks.

I wear real Panama hats and buy them here. I highly recommend them. They come in many different styles and are great for keep the summer sun off your pate.

Do’s:
Fedora, Australian leather hat, weather-beaten cowboy hat (possibly with irony).

Don’ts:
Pork pie hat, beanie, bowler, straw hat.

Your mileage may vary. Head shape and size matter. What you need to do is go to a hat shop. Not a shop that also sells a few hats. A hat shop. Spend some time. Try things on. Alone and with a friend.

Must I say it again? Do NOT wear a pork pie hat.

I’d say ball cap or beret.

So far, I have checked out each of the respondents, and the Irish/European caps look the least repugnant. I mean, I really want to wear a Fedora, but that looks like an affectation in today’s world.

@Imadethisupwithnoforethought Perhaps you only say that because you don’t wear a hat. All hats are going to feel like an affectation if you are changing your style. And fuck what anyone else thinks. If you wear it like you mean it, it will be awesome.

@glacial Thank you. You just kicked my ass appropriately, I think.

@Imadethisupwithnoforethought :)

If you’re gonna wear a fedora, you need to get a leather jacket and a bullwhip to go with it.

A baseball cap with the insignia of a sports team, worn bill forward, will not identify you as a hipster wannabe. Just don’t wear a Texas Rangers or New York Yankees hat. They suck.

I try on hats until I find one that is both comfortable and looks good to me when I look in the mirror. I live in Alberta (North of Montana) and I like light-weight western style felt hats. Some call then cowboy hats.

Amazed no one suggested asshat, given that a few populate these pages :-)

I know a few guys who wear caps such as @chyna suggested. They are all of different ages too and wear a cap while dressed smart casual and look cool, but not like they’re trying to look hip.

Ok, honestly, because we no longer have a culture where male headgear (other than the gimmecap) is the norm; there is no hat that you can wear that will not single you out as “odd”.

Not that I am suggesting you do not do it if you want too.

And once you are inside it is polite to remove your headgear, and expose your wearmarks, anyway.

Wear a crusher and put it in your pocket when working.

I don’t like wearing hats—never have—but like you, I’ve taken to wearing baseball caps to protect from the sun, althought I’m not bald. I see guys in really cool-looking caps but can never find them in stores.

Sheepskin and leather trapper hat

The Russian version

Without the fur

Top right My uncle, the bombardier, in 1942.

I am willing to be as odd as I please. At my age, I feel no concern to conform to any style or convention other than what keeps my head warm enough and keeps the intense sun off my expanding unupholstered patch on the top of my head.