1
Best Pattern
The Pioneer Women’s Fedora Hat with Embroidered Brim
Now 25% Off
Credit: WalmartThis gorgeous fedora may be blue, but you'll be anything but when you're wearing it! The deep navy hat is made even cuter with light blue floral embroidery on both sides of the brim.
2
Best Faux Suede
Faux Suede Baseball Cap
Credit: Amazon
This faux suede look is easy to throw on! Plus, it easily add some cozy texture to any outfit as the weather cools down. Pair it with a moto jacket or plaid shirt for even more flair.
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3
Ree's Style
The Pioneer Women’s Fedora Hat with Embroidered Band
Credit: Walmart
Summer may be over, but that doesn't mean the time for wearing bright colors has to be! This fedora from Ree's clothing line features colorful red and yellow flowers to add a pop of color to your fall palette.
4
Versatile Pick
Carhartt Rib Knit Beanie
Credit: Carhartt
You can't go wrong with a classic knit beanie during the color months! This one is made of an acrylic rib knit that's perfectly soft and stretchy and will go with so many outfits.
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5
Under $20
The Pioneer Women’s Boho Fedora Hat with Embroidered Band
Credit: Walmart
This cream and tan fedora from Ree's line will add a fun touch to pumpkin patch outfits and everyday looks alike! It features a faux suede finish and an adorable exterior band with boho-chic embroidery.
6
Best Bucket
Plaid Faux Fur Bucket Hat
Credit: Amazon
Keep your ears nicely covered as that crisp fall breeze rolls in. This bucket style is oh-so-trendy and just as cozy. Plus, when you buy it in a fun plaid pattern, it makes the perfect statement piece!
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7
Best Beaded
The Pioneer Women’s Straw Cowgirl Hat with Beaded Band
Now 64% Off
Credit: WalmartThis adorable cowgirl hat comes in both white and black so that you can curate it to your own personal fall outfit vibe. With its beaded band, this straw hat is the perfect way to add a subtle flair to any look!
8
48,000+ Reviews
Slouchy Knit Beanie
Credit: Amazon
This chunky cable knit beanie has over 48,000 five-star reviews on Amazon. Reviewers say it has just the right amount of "slouch." It's sure to keep you warm on breezy days, too!
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9
Best Western
Cash Cowboy Hat
Credit: Free People
You'll want to don this classic cowboy-inspired wool felt hat plenty of times throughout the season. The silhouette features a crease crown and upturned brim. You can also find an interior ribbon adjuster for the perfect fit.
10
Best Fedora
Classic Wool Fedora with Belt Buckle
Credit: Amazon
Most fashion trends come and go, but fedoras have been in style for more than 100 years. This popular Amazon buy is made of a blend of wool and polyester, so it's cheaper than 100-percent wool styles—and it comes in 20-plus color combos.
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11
Best Floppy
Lanzom Retro Wide Brim Floppy Hat
Credit: Amazon
This highly rated hat comes in a bunch of colors and ribbon styles so you can pick the combo that pairs best with your fall wardrobe. It's lightweight enough to wear in the sun and stylish enough to dress up.
12
Editor's Pick
Dahlia Boater
Now 15% Off
Credit: Gigi PipWith its signature flat brim and clean lines, this sophisticated find will make you stand out. It's made of high quality Australian wool and has an adjustable fit band inside for the best fit possible.
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13
Best Newsboy
PanPacSight Women's Newsboy Hat
Credit: Amazon
This affordable vintage-style cap comes in a bunch of fall-friendly styles. Choose from tweed, plaid, faux suede, and more.
14
Best Baseball Cap
Classic Corduroy Cotton Baseball Cap
Credit: Amazon
Throw on a baseball cap...without looking like you just threw on a baseball cap. This corduroy hat is dressier than the usual canvas or cotton. The blue-grey is a nice choice for fall, but it also comes in ten other colors.
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15
Cute Cloche
Packable Cloche Hat
Now 17% Off
Credit: AmazonIf you like the idea of a bucket hat but want to get a little dressier, go for a cloche! Typically, they are more structured, but this pick is perfect for fall. It's packable, so you can just grab it when you need. Plus, it's made of a polyester blend instead of wool, so it's not too warm.
Now 20% Off
Credit: AmazonChannel the effortless cool of French girl beauty with this classic wool beret. It comes in 40-plus different colors so you can coordinate with your fall coats.
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17
Fun Fisherman
Fiddler Fisherman Cap
Credit: Nordstrom
A subtle rope trim and rich herringbone texture add flair to this classic fisherman-style cap. Note: It runs large, so size down for a better fit.
18
20+ Colors
Wide Brim Felt Fedora with Leopard Belt Buckle
Credit: Amazon
The olive green color is perfect for fall, and the leopard band is a subtle and stylish way to incorporate the animal print trend. Plus, this hat has thousands of five-star Amazon reviews and comes in over 20 fun colors.
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19
6,500+ Reviews
Bienvenu Wide Brim Floppy Hat
Credit: Amazon
Fans of the floppy look will love this 100% wool hat. The four-inch brim is wide enough to shield your face from the sun, but not so wide that it'll fall into your line of vision.
20
Best for Working Out
Fast and Free Running Hat
Credit: Lululemon
This super cute cap is made of lightweight stretch fabric, so it's perfect for traveling or exercising. And you don't have to worry about breaking a sweat: It has a quick-drying sweatband to wick moisture away.

Macie Reynolds is the assistant editor of E-Commerce and SEO for The Pioneer Woman.

Nitya Rao is the editorial assistant at The Pioneer Woman, covering stories ranging from food, fashion, beauty, lifestyle, news, and more.
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