From Our EIC: It's Freezing, And I Look Like an Idiot in Winter Hats – InsideHook

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Considering what’s been going on elsewhere in the country this week, we’ve had it pretty good here in New York, and I’m fortunate to be able to say that the biggest inconvenience the world has thrown at me is a few consecutive days of wind chill factors in the single digits.
This recent cold streak, though, has revealed a glaring hole in my winter wardrobe: I do not own appropriate cold-weather headwear.
Now, yes, I of course own lots of baseball caps of various materials: standard cotton, corduroy, tweed, for example. But, while I’m well aware of the notion that your body loses a significant amount of heat through your head (is this true, even?) and that, thus, even a baseball cap would go a long way in keeping me warm, the style would not address my single biggest concern, which is that, ho-ly shit, my ears get so cold so fast that after five minutes outside it feels like they’re going to turn to stone and fall off my head.
I don’t know if it has to do with getting old — I certainly don’t remember this being a thing when I was a kid — but it is so painful that by Wednesday of this week, I gave in and dug out an old REI Co-op beanie I used to wear when I was a committed runner, and I reluctantly wore it on my morning commute.
The problem with this is that, for some reason, I look like an absolute idiot in a beanie. Like, really stupid. I can’t tell if my head is big or just weirdly shaped, but it is not good. And also, by the time I get to work and take it off, my hair is a staticky mess, sticking up and out in some places and badly matted down in others. And just like that, my day is ruined.
So I am officially on a quest for a new hat to get me through the rest of this winter and many more to come — and I’m not yet prepared to rule out a beanie. Maybe a nicer one will fit better or just look cooler? Or maybe someone will tell me that I’m being too hard on myself and I don’t actually look that bad? And maybe concerns over my hair will be rendered moot because I’m so happy with how I look in it that I’ll just leave it on all day? A man can dream. 
Below, some winter hat options that have caught my eye. Let me know if you have any other suggestions.
Given that I’ve already said I’m uncomfortable with how I look in a beanie, I probably should not opt for one in which I could be seen from halfway across town, but I always envy people who can pull this off. It’s made here in the U.S., and it does come in a handful of less attention-grabbing colors if that’s more your speed.
I’ve grown quite fond of many of Buck Mason’s offerings over the past year or so, and I have every bit of faith that this thick cotton number would perform admirably.
Because who doesn’t want to live out their deepest, darkest Steve Zissou fantasies? Via Alex Mill, no less.
I would like to think I am the type of person who could get away with wearing this hat, even though I’ve never gone hunting and probably can’t even accurately define what people mean when they say “in the backcountry,” but it’s probably out of my league.
I don’t love the idea of a Patagonia hat with ear flaps, as I worry it reads a little too bro-y, but it definitely gets points for increased wearability over the Filson option above.
I feel like this could be a really good, utilitarian option that covers my ears without being too aggressively styled. My concern is that it feels somewhat adjacent to those around-the-head ear warmer things lots of business types wear.
Could this be the one? It’s been around since 1903, so it’s steeped in history and boasting enough heritage to carry some serious cred. The ear flaps are small enough to be effective without being cartoonish, and they even fold up and tie in the front when not in use. A nice touch that I think could provide just the right amount of jauntiness.
We’ve put in the work researching, reviewing and rounding up all the shirts, jackets, shoes and accessories you’ll need this season, whether it’s for yourself or for gifting purposes. Sign up here for weekly style inspo direct to your inbox.
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