The Best Fall-Appropriate Hats for Men

Tweed, flannel, corduroy and all the other coziest fabrics imaginable

September 17, 2020 12:12 pm
Best Fall hats for men

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This article is part of our Fall Style Guide, a fortnight-long series aimed at helping you figure out how to dress for the coming season, which, as we’ve become accustomed to saying, is going to be quite like any that came before it. At least you’ll look good, though, right?

The accepted wisdom is that fall is great because it means you’re finally allowed to start wearing all the best clothes again: pants, sweaters, blazers, light jackets, etc., all done up in richly textured fabrics that make everyone look and feel better.

But there’s another little perk of the season that no one ever really talks about: all the fabrics that make those other garments so enjoyable are also used to make seasonally appropriate hats. One of the low-key greatest pleasures of the year for me is when I hang up the faded red, lightweight cotton Barbour cap I bought in Cape Cod a few years ago and pull out the heavyweight olive tweed one I got at an Orvis on Long Island longer ago than I can even remember.

That hat, it turns out, has seen better days. So I started shopping around for a new one, and, well, here’s what I found.


Huckberry Ebbets Field Explorer’s Cap

Ebbets Field makes some of the highest quality vintage-inspired baseball caps in the world, and while I encourage you to browse their site and marvel at the vast selection, I also think you could do far worse than just picking up this subtly branded Huckberry collaboration with the brand, featuring a simple capital H and an adjustable strap.


L.L. Bean Wool-Blend Ball Cap

When fall finally rolls around, L.L. Bean really starts to shine. They do cozy, rugged shit better than just about anyone, and this simple but handsome wool cap, with its contrasting color blocks, is perfectly on brand.


Orvis Waxed-Cotton Ball Cap

Another one of the season’s best fabrics is waxed cotton, which is basically just regular cotton with a wax finish to keep it water-resistant. It also adds a nice texture that gets better with age. Orvis is among the brands most associated with the fabric, and this hat is pretty much begging to be worn for years and years to come.


Patagonia Recycled Wool Cap

A little bit of a different vibe on this one, as we switch to the lower-profile five-panel style. Patagonia used a blend of 60% recycled wool, 30% recycled polyester and 10% recycled nylon to construct a warm, durable hat that’ll look cool on the trails or around town. I’m partial to the plaid option, but all are great.

Todd Snyder

Todd Snyder x New Era Selvedge Chino Dad Hat

My dad only ever wore Titleist golf hats, so I’ve never quite understood this whole “dad hat” thing, but whatever: it just means it’s a somewhat floppy and low-profile. Todd Snyder’s is made of rugged twill and features an adjustable strap that boasts a sneaky little selvedge line.


J.Crew Garment-Dyed Corduroy Cap

Oh yeah, now we’re talking. Faded, medium-wale corduroy with an adjustable leather strap. It’s floppy and soft-looking, and I want it in every color.

Deso Supply

Deso Supply Co. Everywhere In Between 5-Panel

A nice option for the retro-minded minimalist, this flat-brim number from Deso Supply Co. has an understated badge and one of those rope things across the top of the brim that seems to serve no purpose whatsoever aside from looking cool.

Brooks Brothers

Brooks Brothers Harris Tweed Baseball Cap

This is the closest I’ve found to my beloved and beat-to-shit tweed Orvis hat I wrote about in the intro you probably skipped (it’s cool, I always skip them too). I like to imagine every single character on Succession is wearing this hat right this very second.


Filson Smokey Bear Low-Profile Cap

Uh, it’s a brown corduroy hat with a fucking Smokey Bear emblazoned across the front. I’m not really sure what else I can say to convince you to buy this. Except maybe that it’s made by Filson and will thus last you approximately 100 years.

Rowing Blazers

Rowing Blazers x New Era Balloon Hat

So one of the common misconceptions about fall is that it’s reserved exclusively for earth tones and generally darker colors. Not so. Observe this perfectly fall-appropriate green New Era hat from Rowing Blazers, and relish in the bright colors and total extreme whimsy of the balloon. A little bit of color never hurt anyone, even in fall.


Noah Packable 4-Panel

A low-profile four-panel from the streetwear kings at Noah, done in a nice subtle plaid and featuring metal eyelets on the side for breathability. This one’s also got a foam bill, so it’s going to be extra pliable.

Only NY

Only NY Waxed-Cotton Collegiate Hat

Waxed cotton, a flat brim, an unstructured dome, a subdued plaid and a nice college-style logo proving you’re cool enough to have gone even a step deeper into the streetwear game than the Noah hat above.

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