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The Best Wool Hats Will Upgrade Your Headwear Game This Season

A guy’s rotation of style essentials needs variety and flavor, with versatility thrown in there, too. This is where your headwear rotation can actually make quite the difference — yes, we’re serious — and this is where the best wool hats add a little something different to your look. Sure, you might be used to wearing an athletic logo hat to the golf course or to go for a run, but when we’re talking the best wool hats, we’re thinking of something with a heritage feel and a bit of a throwback look.

Don’t get it twisted, though: We’re not thinking of wool beanies, especially not in the warmer months. A wool cap is more visually interesting and appealing than a plain ole athletic men’s hat, and it looks better (much better!) with more standard casual gear, be it your favorite pocket T-shirt or a denim jacket, tan chinos and white sneakers. Top it off with a stylish wool baseball cap and call it good — think of it like an upgrade to your everyday carry essentials.

Why Go With a Wool Hat?

For starters, that versatility we mentioned is key. The right wool hat looks more at home with off-duty gear than a standard baseball cap does. Plus, most of the best wool hats are just plain, well, cooler — there’s a reason so many wool caps today look like they’re from another era. That’s because they’re based on designs from that era (think of Robert Redford in The Natural, for instance).

Wool caps, however, have some drawbacks. For some, wool caps can be too hot or too restrictive. Or perhaps, you actually tend to only wear cap when working out or golfing, or pursuing another outdoor-minded activity — in this case, a performance ballcap might be your best bet. It’s also worth noting that some wool caps are much pricier (because of the material and construction) than a more standard ballcap.

And some might find a wool ball cap too distracting, or they might prefer a hat without a logo. In this case, you’ve still got options. But by and large, the best wool caps add some stylish flair and a touch of throwback looks to your favorite everyday ensembles, so be sure you’ve found the right one with our top picks.


1. Ebbets Field Flannels Brooklyn Eagles 1935 Vintage Ballcap


If you’ve kept up with the world of headwear over the years, you’ve perhaps heard of Ebbets Field, which produces true-to-form caps based on archival team designs, like the Brooklyn Eagles. Of course, the company’s name is spot-on for a brand that nods to old-school baseball hats. They offer dozens of options in seriously cool, eye-catching designsand the 100 percent wool construction is also a nod to the past.

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Courtesy of Ebbets Field Flannels


2. Todd Snyder New Era Yankees Cap


Todd Snyder excels at taking everyday menswear staples and elevating them. For his take on the classic New Era New York Yankees hat, Snyder swapped the standard polyester for premium lambswool and added a stylish suiting-inspired chalk stripe. The fitted cap is available in a range of sizes.

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Courtesy of Todd Snyder

3. Everlane Wool Five-Panel Cap


Leave it to Everlane to strike the right balance between affordability and style once more, courtesy of this wool cap in a more unique five-panel design. The blend of nylon, wool and elastane ensures durability and a comfortable fit on your noggin, while colors like Heather Grey seal the deal in terms of neutral, wear-with-anything style. Plus, the price is just right (under $30, to be exact).

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Courtesy of Everlane


4. L.L. Bean Wool-Blend Ball Cap


From time to time, you simply want a straightforward wool hat you can throw on at a moment’s notice without missing a beat. L.L. Bean provides that here, and quite handily, using its penchant for heritage quality combined with an eye for go-anywhere style. The waxed cotton visor is a weather-ready touch that contrasts nicely with the charcoal wool-blend fabric, and this one is priced to sell at just under $30.

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Courtesy of L.L. Bean


5. American Trench Melton Wool Cap


The idea of taking the extra time and care to make things in the United States is something we can’t help but appreciate here at SPY, and this New York-made version takes things to the next level by way of Melton Wool cloth. The rich olive color is visually striking and pairs nicely with light wash or dark blue denim and a classic white tee, while the leather strap is another heritage detail that helps this cap stand apart from the pack.

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Courtesy of American Trench


6. Stetson Plano Wool Cap Men


Stetson is the most beloved American hatmaker, but they’re better known for their wool cowboy hats. They also make baseball caps, such as this cap made from a blend of 85% wool and 15% polyamide. It has a subtle herringbone pattern and a metal logo label. Four colors are available. This cap is fitted, so you’ll need to choose your size correctly.

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Courtesy of Amazon

7. Brunello Cucinelli Embroidered Virgin Wool Baseball Cap


Yes, it’s possible to turn the ballcap into a luxury item, especially in the hands of Brunello Cucinelli. The legendary designer somehow manages to make the ballcap feel fresh, crisp and dressy, particularly given the fact that it’s made from virgin wool. The logo is a subtle, luxurious touch, while the leather back pull-tab is also a nice added detail. If ever a baseball cap could be dressy, it’s a wool hat done by a luxury designer.

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Courtesy of Mr. Porter


8. Polo Wool-Blend Herringbone Ball Cap


It doesn’t get much more classic than Ralph Lauren, and this cap features a sport-inspired “P” logo with a leather buckle strap on the back. The cap is made from a blend of wool and polyester, and its finished in a herringbone pattern that’s perfect for fall and winter.

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Courtesy of Polo Ralph Lauren

9. J Crew Heritage Wool Blend Baseball Cap


The bright red version of this cap either calls to mind Holden Caulfield or, well, you know who. If red hats are ruined forever for you, J Crew also offers a softer maroon color it calls burnt henna, as well as navy. And if you can’t choose between the colors, the fall cocktail mix includes maroon, red, navy and green. The cap is made from a blend of wool and polyester, and it has an elasticated back. It’s available in small/medium and large/x-large.

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Courtesy of J Crew

10. Noah Green Wool Cap


Noah has quickly established itself as one of the best streetwear brands by blending hype, prep and classic menswear in an effortless way. This collegiate-inspired cap features a yellow “N” on a dark green background. The hat is made in Canada from 100% wool.

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Courtesy of SSENSE

11. Madewell Wool-Blend Baseball Cap


Madewell’s logoless baseball cap comes in autumnal colors like “Heather Coal,” “Dried Clover” and “Roasted Espresso” or, put simply, gray, green and brown. The cap has an adjustable buckle on the back and is made from a blend of wool and viscose. Though it’s a unisex style, it’s better suited for larger heads.

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Courtesy of Madewell

12. Allbirds The Cap


Their shoes are frankly a little bland, but Allbirds has a decent selection of sustainably-minded accessories and workout gear. This cap has a minimalist design and is made from a blend of merino wool, nylon and spandex. The cap is adjustable and designed to be unisex. It’s available in a range of neutral shades.

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Courtesy of Allbirds

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