The Best Wool Hats Will Upgrade Your Headwear Game This Season

Model wearing a stylish wool hat
Courtesy of Ebbets Field Flannels

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 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 cap looks more at home with off-duty gear than a baseball cap does — a cap with an athletic logo can feel out of place aside from sporting pursuits, like golf. 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.

Ebbets Field Flannels Brooklyn Eagles Cap Courtesy of Ebbets Field Flannels


2. Harley-Davidson x Champion x Todd Snyder HDMC Hat


The idea of one of the country’s foremost menswear designers stepping up and making a seriously cool wool hat is an exciting prospect, and this is a standout among wool hats as far as we’re concerned. Todd Snyder teamed up with Harley-Davidson on a rugged, road-ready collection, and turned to Ebbets Field Flannels to make this bold, 100 percent wool hat. Time to rev up your engines, folks.

Todd Snyder x Champion x Harley-Davidson HDMC Hat Courtesy of Todd Snyder


3. NN07 Wool-Blend Flannel Baseball Cap


Minimal style can sometimes be the name of the game in the accessories department, especially if it’s a simple, no-frills baseball cap you seek. NN07 has nailed the right balance between rugged and refined with wool-blend flannel fabric in a deep gray color, the kind that pairs well with anything (including patterned shirts for a nice balance between eye-catching and subtle). Plus, it’s on sale right now.

NN07 Wool-Blend Hat Courtesy of MR. PORTER


4. 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).

Everlane Wool-Blend Five-Panel Hat Courtesy of Everlane


5. 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.

L.L. Bean Wool-Blend Hat Courtesy of L.L. Bean


6. 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.

American Trench Melton Wool Cap Courtesy of American Trench


7. BRADY Wool Baseball Cap


If you’re a fan of NFL legend Tom Brady, or simply of his new sportswear-meets-menswear brand, this is the bold logo cap for you. Like more traditional hats (say, New Era), it looks like it’s what you’d call a “fitted cap” — with no back strap — for a super-clean, sporty yet versatile look. It’s also available in a versatile Navy colorway, which you can pair up with anything in your style rotation.

BRADY Wool Ballcap Courtesy of BRADY


8. 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.

Brunello Cucinelli Embroidered Wool Cap Courtesy of MR. PORTER


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