Sure, warm-weather hats like straw hats and visors are great for summer vacations and days spent lying out by the pool, but the chic fedoras, slim berets, cool baseball caps, and cozy beanies that come out in autumn provide even more opportunities to hide bad hair days and accessorize like a pro. Ahead, shop the best cool-weather headwear you'll want to pair with your stylish fall outfits (and check out our guide to what's trending for fall 2021).
This teddy bear shearling hat has UV protection, so you can wear it from the beach to the bonfire.
Accessorize your accessory. Upgrade your basic felt hat with an edgy barrage of gold safety pins.
Take a classic and give it a modern twist this season with this color-blocked, slate blue beret.
This hat is a two-for-one: Its pattern, inspired by Pennsylvania Dutch quiltings, is completely reversible.
Made from recycled materials, this slouchy beanie 2-pack is hard to pass up, especially when it's under $15. Sport these affordable essentials with all your weekday casual looks.
We love the homespun look of this beanie that is hand knit, in small quantities, in Canada.
Bucket hats aren't just for summer. This shearling lined hat will keep your head both warm and stylish.
Some days just call for a clear vinyl bucket hat—and this Clyde hat is perfect for rain or shine.
Nothing is more quintessentially fall than a tartan check hat. Pair it with your cable knits and corduroys.
This always-timeless gray felt fedora will become a staple in your closet. Wear to add a cozy laid-back touch to your cold-weather looks.
Crafted from recycled cotton and polyester, this mixed-media hat has a cool asymmetrical fit.
This versatile short-brimmed hat will play up any fall look. Combine the staple with anything, from sleek knits and rugged jackets to your other fall favorites.
Tap into your fantasy of strutting down the Champs-Elysées by adding a hint of Parisian-girl chic to any of your everyday looks. This textured beret will bring that extra something to your fall daytime looks.
Pair this "borrowed from the boys"-style fedora with your favorite coats and jackets. The wide brim and vintage green color will make a statement this fall.
This plush tie-dye bucket hat is a street style essential. Keep your looks original with this New York brand—each of their hats are made by hand, so no two hats are ever the same.
This Eugenia Kim wide-brim hat with gold pin embellishment and folded detail is your new go-to. Pair with any of your cold-weather favorites for your next getaway.
For traditional silhouettes with modern details, Gigi Burris does it best. This monochromatic wide-brim hat will go with everything from your best knit dresses to your favorite trench coat this fall.
This one is for the bride who is looking to show off her personal style! This Maison Michel boater hat, crafted by couture milliners, has a delicate veil in front and is the perfect chic alternative to a traditional veil this season.
Elder Statesman's signature tie-dye and California-cool vibes are all here in this super-soft cashmere beanie. Easily stay warm the rest of the year by adding this pop of color to any outfit.
Janessa Leone's "Frankie" hat has a double leather band that gives a polished look to the pure-white short-brim hat. Its neutral tones will complement all the cold-weather knits you're dying to pull out of storage.
I thought this vintage-inspired bucket hat (perfect for a chic City Hall wedding) existed only in my dreams! Pair this with an tailored ivory tuxedo jacket and straight-legged pants for your big day.