Yes, You Actually Are a Hat Person: Six Hats for the Non-Hat Guy

Some iconic men who wear hats well; plus some to buy now to try yourself. Source: (clockwise from top left) Andrew MacLear/Getty Images (Keith Richards); MR PORTER; Silver Screen Collection/Hulton Archive/Getty Images (Marlon Brando); Barneys New York; GAB Archive/Redferns (Tom Waits); Barneys New York; Anwar Hussein/Hulton Archive/Getty Images (Steve McQueen); Stormy Kromer

I can’t tell you how often someone tells me, “I love your hat! I wish I could wear one, but I’m not a hat person.”

Not true, my friend. You just haven’t found the right one.

December is the perfect month for experimentation. It’s cold enough outside to justify covering your head, which means you don’t owe an explanation to anyone about why you’re wearing a hat. Not that you ever do, but less so in wintertime. It’s also filled with holiday travel. That means you can try something new far away from the maddening crowd, whether your own personal maddening crowd means your too-cool friends (in which case, try the hat around family members, or vice versa). What’s that adage? An artist gets no love in his hometown? This, too, applies to those inclined to even the slightest sartorial exploration. Don’t let the haters get you down.

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Hat Buying 101

  • Beg for, borrow, or steal a hat. Wear it for an hour away from people who care. See how you feel. Take your temperature. Take your pulse. There, how does that feel? See, you’re fine. Now do the same with a different option. How does that one make you feel? Compare.
  • Fact: Every face, every head shape, every hairstyle and color can wear a hat.
  • It’s just a matter of finding the right one for you. So, you must try on a lot of them. Then note how they sit over your eyes, how their brims and tops change your mood. Are you self-conscious when you wear it? Or does it make you feel comfortable? Pay attention to this subtlety. Just like cars and dogs, the hat should never upstage you. It should enhance who you already are.
  • Take stock of your lifestyle. Do you live in the city? In the mountains? On the beach? Buy accordingly. By which I mean avoid straw boaters in autumnal Manhattan; choose thick wool toques for the Pacific Northwest; shun fedoras universally. (Unless you’re over 70 when anything goes and you presumably know how to dress yourself by now anyway.)
  • Remind yourself: Eventually something will click. It’ll sit angled just so on your brow, the shape perfectly communicating how you think and feel. It’ll be the one that makes you wish you had found it sooner.

You’ll know it when you see it. You can’t force a good hat; it has to find you. But below are a few suggestions to get you started.

The Casual Dandy

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A Helsinski cashmere cap by Lock & Co Hatters. ($265, mrporter.com)

The Hunter

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A hand-stitched red and black plaid Stormy Kromer. ($40, stormykromer.com)

The English Toque

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A cable-knit donegal beanie by Thom Browne. ($140, barneys.com)

The Untraditional Ballcap

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A Ventile cap by Best Made Company. ($75, bestmadeco.com)

The Trapper

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A fur-trim aviator hat by Crown Cap. ($460, barneys.com)

The Downtown Beanie

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A merino wool-blend colorblock beanie by Alexander Wang. ($275, barneys.com)

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