Hats are awesome year round, but there’s a special place in our hearts for them during autumn. There’s just something about the cooler weather and long days that make a hat the perfect transition accessory for navigating our summer-to-winter wardrobe. Scroll on for six of our fave toppers, each paired with gorgeous hairstyles to make your look feel magical.

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1. Dressed-Up Ponytail + Leather Baseball Cap ($30): There is something classic and sexy about dressing up a typically sporty item, and leather baseball caps might just be the perfect way to do this. Supermodels and superstars like Miranda Kerr, Rihanna, the Kardashians and Hayden Panetierre are all rocking the look. Pair this hat with a dressed-up ponytail and slam-dunk the chic and sporty trend. (via Brit + Co)

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2. Messy Side Braid + Floppy Wide Brim ($23): The floppy wide brim is perhaps the staple hat to own. This accessory is uber versatile — we’re talking Kentucky Derby to Burning Man versatile. Dress it up with a fancy updo and chic outfit, or dress it down with some boho waves. You really can’t go wrong with this one, but we suggest a messy side braid. Flop on, people. Flop on. (via Brit + Co)

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3. Crown Braid + Colorful Beanie ($57): Beanies are the best, right? They are easy, comfortable and, moreover, practical (no one likes cold ears). Since more often than not a beanie hides the back of your head, try wearing a cool crown braid in front. It will peek out from the beanie, rounding out a casual look and adding flare. (via Once Wed)

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4. Straight Hair + Wide-Brim Fedora ($64): The leather rancher is another classic staple that adds some easy style to your look. Channel your inner bohemian cowgirl and pair this topper with the locks that all celebs are rockin’: super glam straight hair. (via Brit + Co)

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5. Sleek Waves + Boater ($38): Wearing a boater just screams style and sophistication. We suggest pairing this hat with a clean, simple style, like sleek waves. The flattop and strong brim line make the boater more of a statement piece than an accessory, so let the hat do the talking! (via Brit + Co)

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6. Fishtail Pigtails + Wool Hat ($49): We’ve seen many a wool hat, but this one’s lovely lilac shade makes it a must-own in our books. Pair it with messy fishtail-braid pigtails to add a level of style reminiscent of the hat’s traditional Spanish origins with a bohemian twist. (via Brit + Co)

Do you have a favorite hat and hairstyle combo? Tell us in the comments section below!