What kind of hat should I wear?

June 1, 2009 4:50 PM

What kind of hat should I wear?

I'm tired of baseball hats, and I'd like to start wearing a new kind of hat. I'm looking for something stylish that won't make me look like a hipster doofus. I would mostly wear it while out and about with friends. Throw me some ideas.

I saw a hat a liked recently. It was shaped sort of like this, and it had a signature on the side. Any ideas what brand that would be?

posted by diogenes to clothing, beauty, & fashion (30 comments total)

won't make me look like a hipster doofus

A fez? A Galero? From your link, it seems your definition of hipster differs from that of many of the hipsters in my town.
posted by cmoj at 4:57 PM on June 1

Are you a man or a woman?
posted by halogen at 5:02 PM on June 1 [1 favorite has favorites]

If the hat I linked to falls into the hipster doofus category, feel free to let me know! I can't even tell anymore...
posted by diogenes at 5:03 PM on June 1

Man.
posted by diogenes at 5:03 PM on June 1

For a 33-year-old man, the hat you linked to would be pretty ridiculous, in my opinion. I only ever see these on teenage girls in winter.
posted by halogen at 5:11 PM on June 1

I don't believe a hat makes a man; rather a man makes a hat. Therefore, I'd wear whatever hat looks good on you, regardless as to whether or not it makes you look like a hipster, doofus, or combination thereof. Even a fedora.

I promote herringbone flat caps, panama hats, and their use by non-hipsters. I figure the more people like us wear them, the less they will be considered hipster.

But please don't wear a fedora.
posted by jabberjaw at 5:14 PM on June 1 [2 favorites has favorites]

I wear a beret like this when it's cold and wet.

Concerns about hipsterism shouldn't take priority over warmth and dryness.
posted by Fiasco da Gama at 5:22 PM on June 1 [1 favorite has favorites]

The hat you link to is the definition of "hipster doofus" in my opinion.

You can wear whatever you want, but in general men are limited in hat options to ball caps, visors (if you're golfing), knit skull caps (in the winter), and a variety of tasteful wide brim hats (if you're hiking or on a boat), or fedora style hats (if the rest of your wardrobe can support one, and the setting is appropriate.)

In other words, men's head wear is intricately linked to activity. Which is why the ball cap is ubiquitous, can be worn with anything from a t-shirt to a blazer, while other hats require specific settings and activities.

Deviate from this and you risk becoming a "hipster doofus," a sad sack indeed, for no one, but the most forgiving person, ever takes a hipster serious.
posted by wfrgms at 5:23 PM on June 1 [3 favorites has favorites]

I don't understand the worry over being taken for a "hipster doofus." Wear what looks good on you and don't worry about what idiots might think. I recommend a visit to a good hat store; the salespeople will have a good sense of what will suit you, and you'll have plenty of time to check out the possibilities in their mirrors. And there's nothing wrong with fedoras—that's one of the stupidest memes going around. Bogart wasn't a hipster, you moronic whippersnappers.
posted by languagehat at 5:31 PM on June 1 [3 favorites has favorites]

Languagehat is right. When choosing a hat, consider your entire look at the moment and wear a hat that looks good on you with the rest of your outfit. Fedoras are not off-limits unless they don't look good on you with the rest of the outfit.
posted by The World Famous at 5:35 PM on June 1

A flat cap is looking like the way to go. I just want a hat that isn't a baseball hat and doesn't stand out. It seems like anything outside of a baseball cap will draw some attention, but the flat cap seems like the most conservative of the options.

Here's the one I'm considering.

Apparently they're called Ivy caps in the US.
posted by diogenes at 5:44 PM on June 1

The Kangol brand has a ton of options and is, I believe, both classic and trendy without crossing the line to hipster. I think this one is cute, and not too hipster-ish.
posted by tk at 5:44 PM on June 1

I think the first cap you linked looks fine, esp. for your particular head. At no point will anyone ever point a finger and make the body-statcher hipster bellow at you. Neither will people be snickering behind your back. People mostly don't care what hat you wear, it turns out.

Hats are an opportunity to incorporate lots of different styles into your wardrobe. It's a fairly low-stakes fashion risk, especially if you're mostly just looking at various kinds of caps. Buy a bunch of them. Sometimes you wear the hat, and other times the hat's wearing you -- and it takes a little trial and error to figure out which of these is happening with any particular hat. When in doubt, leave house without.
posted by hermitosis at 5:51 PM on June 1 [1 favorite has favorites]

that should have been "body-snatcher"...
posted by hermitosis at 5:52 PM on June 1

I'm going to go against the grain and say wear a cap only when you need it. Really sunny? Super cold? I feel otherwise hats look kind of lame on dudes...just my two cents...
posted by mattsweaters at 6:12 PM on June 1

Kangol makes flat caps in summer and winter fabrics. The summer ones I've seen are polyester/nylon blends that are washable by hand (hang to dry) and keep their shape.
posted by x46 at 6:54 PM on June 1

What about a Greek fisherman's cap?
posted by jgirl at 7:02 PM on June 1

Do you have any bespoke hat shops near you? Millinery is the expensive word for it. Go to one, try on different hats, talk to the staff and let them know what you're looking for. They can help, and you'll get a great idea of your options. You don't have to buy there, but a great place to start.
posted by cestmoi15 at 7:30 PM on June 1

Many years ago, when hats were almost a requirement for men, I had an uncle who made a decent lving by having a store that sold only hats for men. On the entrance arch: WHEN BUYING A HAT, USE YOUR HEAD.
posted by Postroad at 7:32 PM on June 1

I'm hat-obsessed, own many, and have chosen successful hats for many men. I feel qualified to pontificate.

I'm not nuts about the one you linked to- it's thick and a little girly for my taste. Also, you have a somewhat small face (I peeped your photos) and I think a thick hat will look too big and heavy for you. One in a thinner weight fabric will look better, I think. Thick wool hats are kind of annoying, even in winter. Thinner, woven fabric is more comfortable anyway.

Flat caps are good. Make sure it fits narrow on the sides- if the hat is too big, it looks like a mushroom cap and you'll look like a scrawny child. You want a sleek fit, too- not a puffy one: puffy is very bad. But sleekly fitted is good. This one is a little too wide for this man's head. Brad Pitt's oft-worn hat is good- be sure to curve the brim in your palms (don't break the cardboard inside, just give it a nice deep curve). You can often find good ones in large department stores in the old man section. This one is great- all you'd need to do is curve the brim.

For you I'd say a plain colour or a very fine pattern- not a big chunky pattern. I'd say it should pretty much look like a solid colour from across the room. The big bold patterns will look better on people with really big features or very flashy style (like, say, LL Cool J). People with finer features or less contrast on their faces (Brad Pitt or Justin Timberlake) are better off in subtle patterns.

Not all these hats are created equally- the depth and brim length make a huge difference in how they look on different people. Try on at least 10 different ones so you can see how different hats fit, and be choosy. I strongly suggest NOT buying online. Expect to pay at least $50 for a good cabbie hat, although you might luck out in the $20 range. And you can experiment with cocking it juuuust slightly to the side to look really badass. But DO NOT wear it backwards, please. 1990 called and asked us all never to do that again.

Also good on guys your age are Castro-style army hats. They are best when they're totally plain- no buckle, no little belt details, no little air holes, and absolutely no ruffly elastic in the back. Buy them at army surplus stores where you can try on every size. Should run about $12-20. The ones with embroidery, fake worn patches, adjustable straps, or any other geegaws on them are lame and don't tend to fit well. Please don't get a camouflage one, either. Chocolate brown is your best bet.

Good luck!
posted by pseudostrabismus at 7:34 PM on June 1 [15 favorites has favorites]

Oh, and the flat cap you linked is pretty good- but I think it's much better to try it on than to buy online. Different manufacturers' hats fit differently and not all brands will look good on you.
posted by pseudostrabismus at 7:37 PM on June 1

When I clicked on your "badass" link, pseudostrabismus, I got a "403 FORBIDDEN" error. I like the idea that I'm forbidden from seeing badass things.

Regarding hats, it'll be tough to beat pseudostrabismus' advice, but I'd suggest going to a nice second hand shop and trying out a bunch of different options. You can at least get a sense of what styles work and don't, and maybe take some cell phone pictures in the mirror to review later.

And, determine your proper hat size. I've had trouble in the past purchasing properly sized fitted baseball caps because I always guess my hat size wrong when I'm ordering online. Nothing is worse that an ill-fitting fitted cap! Too loose and you're chasing it down the block on any windy day; too tight, and you're battling headaches constantly.
posted by elmer benson at 7:48 PM on June 1

Not a hat guy myself, but my younger cousin just started wearing a grey pork pie hat with a VERY small brim. Actually looks quite stylish on him.
posted by Doctor Suarez at 8:00 PM on June 1

I'm loving my castro style radar visor with it's collapsible brim, but not loving the branding. Why on earth would you stitch SPF 30 on a cap?!
posted by furtive at 8:56 PM on June 1

shoot, I meant the radar cap in slate gray.
posted by furtive at 8:57 PM on June 1

I think the Kangol Ventair 504 looks great on men and women.
posted by aquafortis at 9:40 PM on June 1

Pseudostrabismus, I usually don't mark a best answer, but damn that was a good answer! Thanks :)
posted by diogenes at 6:12 AM on June 2 [1 favorite has favorites]

If you can, go to an honest-to-gosh hat shop and have a pro fit your head (what if you're a Long Oval freak, like me?). They also have seen a lot more people wearing hats than you have, so wear typical clothes and bring some money.

I will cost more than shopping online, but you will get the benefit of their expertise & experience.
posted by wenestvedt at 8:23 AM on June 2

I heard an expression, many years ago; "Never wear a hat with more personality than you".

Also, I think there are several aspects of hat wearing that come into play. For example, I probably wouldn't wear my fedora unless also wearing a jacket or sport coat. Seems to require some dressing up. I have a straw fedora-shaped hat (similar to this) that seems like more of a warm weather hat. Many caps (like the ones pseudostrabismus mentioned) seem to be more fitting for cold/cool weather. And, I think ball caps are extremely casual (i.e. OK with jeans, but don't look right with jacket).

Also, you might want to check out the Fedora Lounge.

Just some random thoughts from a random hat guy.
posted by ObscureReferenceMan at 9:37 AM on June 2

I like my Tilley T3. I don't know whether that's a recommendation or a warning (I'm not exactly stylish or fashionable) but it's a very good hat.
posted by BinaryApe at 3:03 PM on June 2