What are your favorite men's winter hats?

December 10, 2014 12:49 PM

My go-to winter hat for years has been a plain grey knit cap. I was recently informed by a friend, and then another friend who agreed, and then another that the hat makes me look "like a bum," (in their words). I like having warm ears and a warm head, but I'd also like a better winter head covering that doesn't look frumpy and low effort. What's some good head gear that is both warm and relatively fashionable.

Specifics:
I'm willing to spend up to 30 dollars.

I'm looking for it to fit with most street-wear. My style is sort of boring (a button up shirt, jeans, sneakers, and a jacket) in general.

I'm willing to entertain all sorts of, uh, genres of hats. However, my main concern is something that directly covers my ears, since having cold ears is the worst.

posted by codacorolla to Clothing, Beauty, & Fashion (17 answers total)

Lumberjack/trapper hats are great for keeping your ears warm, as are knitted Peruvian style hats. Or you could just stick with what you're wearing and tell your friends to bugger off ;-)
posted by Dorothea_in_Rome at 12:52 PM on December 10, 2014 [2 favorites]

Express is having a sale on cold weather accessories (hats, scarves, etc.) at the moment; 40% off. I have an Express beanie that I wear quite often. They also have a sort of lumberjack/trapper hat in the mix.
posted by axiom at 12:55 PM on December 10, 2014

How about earmuffs? Then you can wear any hat you like. I'm surprised by the comments on the knit cap, though, I thought they were supposed to be relatively in at the moment.
posted by backseatpilot at 12:58 PM on December 10, 2014

If you can scrape together an extra $10 for a quality American-made product, I recommend Stormy Kromer caps. Unlike other hunting caps that require untying, you just yank the ear covers down and up as you like. The brim keeps snow off your face (and, more importantly if relevant, glasses). I linked to L.L. Bean's offerings but they're available all over the internet.
posted by ndg at 1:16 PM on December 10, 2014 [3 favorites]

You refer to it as 'the hat'...so it's been the very same old hat for years and years? Maybe you just need a fresh new one!
posted by mdrew at 1:28 PM on December 10, 2014 [5 favorites]

Clearly you need a cunning hat. But by now that may not be any more fashionable than your old gray watch cap.
posted by Bruce H. at 1:36 PM on December 10, 2014

Tell those friends to update their sense of men's fashion:

David Beckham
Brad Pitt
posted by at at 1:40 PM on December 10, 2014 [2 favorites]

Perhaps just an upgrade of the same style of hat would work? I'm picturing your current plain grey knit cap is of the type that is made of acrylic and you can pick up at Walgreens for like $5 (like this?). If that's the case, then consider a knit cap made of higher quality materials, and perhaps with cables or some other design element to step up your game. Here's a knit wool cashmere hat from Land's End, for example. (The LE hat is a bit out of your price range, but you may be able to find coupon codes or find something similar at other stores.)
posted by misskaz at 2:05 PM on December 10, 2014

My first winter in upstate New York, I stumbled through the door of a menswear shop asking if he had anything for my increasingly numb ears. He put hats on my head until he got to this Kangol with earflaps in black. People say it suits me, personally, but I'm not 100% certain it's a hat for everybody.
posted by Comrade_robot at 2:22 PM on December 10, 2014

Seconding the Stormy Kromer hat. They're made in the Upper Peninsula of Michigan! Yes, that is a big deal.
posted by BostonTerrier at 2:33 PM on December 10, 2014

Shearling, either with earflaps or a brim you can pull over your ears.
posted by brujita at 4:06 PM on December 10, 2014

I once had a terrible crush on a friend of mine, not least because if how attractive he looked in exactly this style of hat.

So unless your particular instantiation of this hat is decaying, stained, or smelly, I call bs.
posted by nat at 5:17 PM on December 10, 2014

My friend, I don't know if you celebrate Christmas, but if you do, and if you have friends or family who have difficulty finding gifts for you, then what you have here is a golden hat-portunity.

Hats aren't that expensive. If you want, you could probably go into a department store like Macy's (or an outdoorsy-type store) and emerge with a pretty good hat.

LL Bean seems to have a particularly nice selection!
posted by amtho at 5:46 PM on December 10, 2014

Maybe it's the color and/or general decreptitude of the hat they are objecting to, more than the design?

I'd think about a ragg wool watch cap; at least to me they scream more "yuppie" than "bum". YMMV of course.

Most other designs of winter hat are going to put you into either Elmer Fudd or hipster territory.
posted by Kadin2048 at 7:08 PM on December 10, 2014

I love my LL Bean Mad Bomber Hat. It's like walking around in my own micro-climate.
posted by schrodycat at 7:32 PM on December 10, 2014

I'm not sure what the generic name for this type of hat is. Not "Russian hat" or "Cossack Hat." However, this style is a great step up from a watch cap. It folds flat, and can be warm. Mine has a fold-down ear flap. I'm sure, with a little searching, you can find one in fake fur.

The fashion industry has done men a disservice by ignoring the man's hat market. Most stores have nothing, NOTHING!, worth wearing. This goes for summer and winter. Actually, i put a lot of blame on JFK. One the day of his inauguration, DDE (the outgoing president) was looking very uncomfortable in silly Homburg and overcoat. JFK went bare-headed sans overcoat, and killed the hat industry.
posted by SemiSalt at 10:32 AM on December 11, 2014

Knit caps are incredibly trendy right now. I agree with posters above that suggest upping your game in the material department, with a cashmere and wool blend.
posted by oneirodynia at 7:08 PM on December 11, 2014