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Wool Hats to Wear This Fall

Most baseball caps are best saved for summer, but woolen ones can be worn well into the next season.

wool baseball caps Gear Patrol

By Evan Malachosky

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I won’t even try to convince you baseball caps work in winter. It’s far too cold out for them by then. Beanies are your best bet. But, in spring, summer, and even fall, baseball caps are perfect, ideal, and acceptable, in that order. You can get away with normal cotton or nylon ones — the kind’s bikers and baseball players wear — in the warmer months, but woolen ones are a necessary upgrade in autumn.

But don’t cling too hard to them, even if you’re someone who claims to be immune to the cold. Take advantage of the window we’re entering: when it’s warm enough that your ears won’t freeze but cold enough to warrant some kind of hat. These fit the bill (pun intended), and most make a colorful statement to boot.

Baseball Caps for Fall

The brand says this cap’s campfire-inspired, but I’d argue it looks a bit more like an old, well-worn flannel. Either way, it’s autumnal for sure and made from 100-percent wool. 

Worried about overspending on something you won’t end up wearing? Go with Madewell’s five panel cap. It’s under $40 bucks and available in three colors.

Norse Projects’ Wool Sports Cap looks reminiscent of early varsity jackets, when they were gray sweaters with crimson Hs on them. This is obviously an N, but it’s knit just the same. 

The New York Yankees cap is the best-selling hat in all of baseball. This isn’t that Yankees, but rather the Black Yankees from the Negro Leagues. Ebbets Field Flannels made this one to honor them. 

This classic Houndstooth cap comes via J. Crew, for under $50 bucks, too, if I may add.

The coolest thing about this baseball cap by Japanese repro brand, The Real McCoy’s, is the message stitched onto the back, as if it were done by someone’s grandma ahead of a big game: “Go #50! Please remain on bleachers ’til game is over.”

Another made-in-Japan option, H.W. Dog’s retro-tinged Baseball Cap comes with a leather adjuster on the back and woolen, vintage “D” on the front.

If you’re going to do it, why not do it big? Missoni’s Jacquard Baseball Cap is doing it big. Its all-over pattern is muted enough, however, as to blend in with other outfits. It doesn’t look as zany on as you’d think. 

Yes, Viberg makes boots, but the brand’s T-shirts and hats hold their own. They’re made with the same commitment to quality and durability, and, of course, classic design. 

Officine Générale further blends prep and ivy styles — they’re already interchangeable in many ways — with this Houndstooth patterned, logo appliquéd Baseball Cap. 

From afar, this is a fine, fairly simple cap. Up close, you notice a few things: it’s made by Visvim, cut from 100-percent wool, and fitted. There are two sizes, small/medium and large/extra-large. 

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