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Good Looking Winter Hats

December 2, 2010 By Joe | Heads up: Buying via our links may result in us getting a commission. Also, we take your privacy rights seriously. Head here to learn more.

The Watch Cap: R.Lauren – $35 | The Cable Cap: J. Crew – $48 | Fair Isle Beanie: B.R. – $30

From the Mailbag:

Hey Joe,

Winter is doing its thing where I live, and the temperature is rather chilly to say the least (the high last Wednesday was 4 degrees).  I’m all set, with my heavy pea coat, gloves, scarves, etc.  However, my head remains, in a word, freezing.  Do you have any ideas for headgear other than a standard beanie?  Something that combines fashion and function, or should I just wear my beanie with pride?

– Aaron

Thanks to Aaron for writing in, and I wish I had a better answer.  You gotta wear your winter hat with pride.  Yes they mess up your hair and yes they make you look, from the neck up, um… phallic.  But the alternatives just aren’t acceptable.

The first problem with other options like driving caps or fedoras is that on most (but not all) men, they look forced.  The second problem is that they all leave your ears unprotected.  And if your ears are stinging because it’s that bitter cold out?  Your hat ain’t doing its job.  It’s got to keep you warm, and that’s why you also need to go with wool and not cotton.

Unlike cotton, wool will still keep you warm even if it gets wet.  And wet things seem to fall from the sky this time of year.  Here’s three basic styles to consider:

Ribbed Watch from Woolrich. Italian cashmere blend. Under $40.

#1. The Watch Cap:  Ralph Lauren Merino Wool – $35.00

Knit with a flip up bottom, watch caps were designed to keep the heads of soldiers or sailors warm when they’re on watch.  Usually they’re dark and match the wearer’s coat (most often a peacoat).  But since Camel is huge this year, flip the script on buying a new camel coat and get a camel/light brown hat instead.  Like this one.  100% merino wool.  Wear it with your black peacoat and it’ll stand out in a good way.  There’s also your local Army/Navy Surplus.

#2. The Cable Cap: J. Crew Wool Mix – $48.00

Cable knits are just more expensive.  But they do offer a little more bulk, warmth, and if you keep it dark, subtle texture.  Women look best in cable knit.  Especially sweaters.  Guys can still pull off a cable knit cap.

#3. The Fair Isle Cap:  Banana Republic Fair Isle Wool Mix Beanie – $29.50

Throwin’ a bone to the Fair Isle fans here.  I’m not a fan of the Fair Isle pattern when it thunders over a sweater like an invading horde.  But if it’s done lightly, in a similar shade, and it’s on something you take off when you come inside like a hat… well then have at it.  Oh, and I’m gonna guess that the hat you see above isn’t made in Scotland.  (Thanks to our pals at TheNextBarStool for the link)

Too boring or minimalist?  Would you wear something like this?  Or this?  What’s your go-to hat?

Filed Under: Accessories Tagged With: beanie, cap, Fall, from the mailbag, good looking winter hats, hat, Winter, winter hat, wool hat

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Comments

  1. OhioHead says

    December 2, 2010 at 6:23 AM

    Love the “watch” style cap, just picked up a burnt orange and heather gray for $2.99 each @ Target yesterday, hate to say it why waste the money when you lose these things…..

  2. Joe says

    December 2, 2010 at 6:43 AM

    @OhioHead: Nice price! Are they wool?

  3. Stephen H says

    December 2, 2010 at 8:11 AM

    I think the wool is worth it if you are going to wear it everyday and don’t have the habit of losing things.

    That being said, I lose everything and will see if I can find a decent wool one on Ebay so it won’t hurt so bad when it’s gone.

  4. Jason says

    December 2, 2010 at 8:37 AM

    I’m prepared to get a little flack for this, but does anyone else wear the “180’s” fleece ear warmers? They keep my ears warm, without messing up my hair, and are low-profile enough to not look like earmuffs from the 1980’s.

  5. Brian says

    December 2, 2010 at 10:16 AM

    Jason – I was just about to comment the same. I stay warm, my hair doesn’t get messed up and they fit easily in my coat pocket when I step inside. What’s not to love?

  6. Pepe says

    December 2, 2010 at 11:09 AM

    @Jason. I already bought a 180. Why would you receive flack for it? Am I breaking a rule? lol

  7. al says

    December 2, 2010 at 12:08 PM

    What is wrong with a real hat with a brim? Check out Filson (and many others) for a good looking wool hat that looks like a hat.

  8. Adam says

    December 2, 2010 at 12:34 PM

    Hey Joe,

    I think I’m a pretty savvy online shopper, but I haven’t found a decent camel peacoat (not 3/4 like banana) for less than $400-500. Got any suggestions? The only one I’ve found is .

  9. Joe says

    December 2, 2010 at 1:32 PM

    @al: Like this one? Terrific that it’s made in the US, affordable at $60… but my ears. My freakin’ ears. They’d get a bit cold. That and hats like that just look forced on some guys (me especially).

  10. Joe says

    December 2, 2010 at 1:49 PM

    @Adam: Camel Peacoat? Double breasted? Just past the waist or mid thigh? I tried on that Banana Republic coat yesterday. Wasn’t real impressed (I have a trench from them that’s incredible. And it’s probably just as warm as their thin wool camel coat)

  11. W. says

    December 2, 2010 at 8:21 PM

    So I guess no one is looking at going in this sort of direction for winter headwear then….?

  12. Adam says

    December 2, 2010 at 9:27 PM

    I’m thinking more past the waist. I’m not too particular on single or double breasted. I currently on a past the waist grey pea coat from gap that i’ve been happy with. There just aren’t many options out there in general.

  13. Yakov says

    December 2, 2010 at 10:02 PM

    I wear the Dome Perignon from Mountain Hard Wear. Completely dorky but it is the driest, warmest hat I’ve ever found.

  14. OhioHead says

    December 3, 2010 at 10:13 AM

    The “watch” caps I referenced from Target are not wool, I would say acrylic, they are quite warm!

    In regards to “camel pea coats” I would suggest going to the local thrift store, I just picked up a “camel colored wool” 3/4 length for $10.00 @ Unique Thrift in Cleveland during their Black Friday sale, my sister is an avid thrifter and knew who the manufacture and it was in very good condition.

  15. Pete says

    December 12, 2010 at 3:19 PM

    If I’m looking at a wool hat, like the “watch” caps, what are the thoughts of getting one from a place like Etsy? It did a quick search and it looks like there’s a variety of styles that are hand-knitted in wool, and the prices seem comparable to those above. Would their quality, warmth, and water-protection likely be just as good?

  16. Joe says

    December 12, 2010 at 8:19 PM

    @Pete: I think in a lot of cases they’ll be better. But, it’s Etsy… and you just never know.

  17. Adam says

    December 28, 2010 at 9:47 AM

    It’s very hard to look respectable in a beanie. Most guys (me included) look too rough / hoodlum-like in one… it definitely take me down several notches. And they mess your hair up. I go with 180s, but of course they aren’t as warm

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