16 Cute Outfits to Wear With Hats This Year

Winter may very well be the best time of the year to pull out all of your hats. While the accessory can be worn year-round, there’s no time like the coldest months of the year to pull out your beanies, baker-boy hats, and wool fedoras. But despite their popularity, they aren’t always easy to pull off. To provide some inspiration, we turned to the street style snaps of fashion girls to steer you in the right direction. You’ll never have to wonder just exactly how to style that beret again.

Go on to see 16 outfits with hats to inspire your cold-weather looks this season.

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Collage Vintage

Match a cool structured hat with a comfy winter sweater and trousers. 

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Keep your head warm with a furry bucket hat, and pair it with a long coat. 

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Try out a colorful beret for the ultimate Parisian chic look. 

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Collage Vintage

Fiddler caps are perfect with a leather jacket. 

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Collage Vintage

Try out a simple beret with a colorful and patterned coat. 

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Collage Vintage

Go for a more simple look and pair a leather cap with a chunky sweater and denim. 

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Take a hint from supermodel Romee Strijd and match a cool red cap with leather pants and ankle boots. 

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For a more bohemian look, try out a brown fiddler cap with wide-leg denim. 

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Pair a statement top with trousers and a simple beret. 

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Opt for a cool all-white look, and pair your ensemble with a graphic beanie. 

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Collage Vintage

For a cool British girl look, try out a checked coat with leather pants and a black fiddler cap.

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Collage Vintage

To get that girl-next-door look, opt for a baseball cap, and dress it up with ankle boots and a structured jacket. 

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We're obsessed with Olivia Palermo's style, and her jeweled cap with a British coat is no exception. 

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Collage Vintage

Try out a fur coat with knee-high boots and a cool fedora. 

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Collage Vintage

Keep warm with a simple beanie and chunky scarves. 

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Collage Vintage

Stay on trend by pairing a large beanie with leather boots and a long skirt.

Next, read about the most stylish holiday gifts of the season.