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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(Image credit: Collage Vintage)

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

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(Image credit: Collage Vintage)

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

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(Image credit: Collage Vintage)

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

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(Image credit: Collage Vintage)

Fiddler caps are perfect with a leather jacket. 

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(Image credit: Collage Vintage)

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

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(Image credit: Collage Vintage)

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

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(Image credit: Getty Images)

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

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(Image credit: Getty Images)

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

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(Image credit: Getty Images)

Pair a statement top with trousers and a simple beret. 

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(Image credit: Getty Images)

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

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(Image credit: 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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(Image credit: 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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(Image credit: Collage Vintage)

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

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(Image credit: Collage Vintage)

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

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(Image credit: Collage Vintage)

Keep warm with a simple beanie and chunky scarves. 

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(Image credit: 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.

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including Vogue.com, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.