The Best Winter Hats for Your Face Shape

There’s just something cool about a woman in a hat. Part mysterious, part sophisticated, totally stylish (not to mention warm), topping your head with a fedora, cloche or beanie is a must as the weather turns cold. But, as with finding the right clothing for your body type, you need to choose the right hat for your face shape. Whether yours is Oval, Square, Round, Long or Heart-shaped, there’s a flattering look out there for you. Here are 10 styles to get you started.

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1Heart Face Shape: Drop in the bucket

When your forehead is wide, but your chin is narrow, a brim can help balance your face’s shape, but if you go too wide, your chin will appear even narrower. One solution: a bucket hat. This tweed Eugenia Kim version has a 2-inch brim—super flattering for Heart-shaped faces.

Eugenia Kim “Genie” bucket hat, $88

2Heart Face Shape: Faux real

Like Oval face shapes, Heart shapes look good in most hat styles. For a trendy, hipster vibe, opt for a slouchy knit beanie. We’re smitten with this wild look from Mars, with its giant faux fur pom-pom on top. Available in maroon, ivory, charcoal and black, we just might need one in every shade.

Mars slouchy beanie, $48

3Long Face Shape: Hats off

To help shorten a long face, try on a hat with a big, circular brim that can be pulled down low on your forehead. Just be sure to avoid hats with high crowns—they’ll just make your face appear even longer.

Ferndale floppy hat, $48

4Long Face Shape: Cloche call

A retro, 1920s-style cloche (that’s French for bell) is not only elegant and sophisticated, but also flatters a long face, as the brim hides your forehead. This felt version features a polka dot band and bow and is lined in paisley. Must. Have.

Goorin Bros. “Jessica Rogers” cloche, $65

5Oval Face Shape: Raspberry beret

An oval face looks pretty—and so en vogue—in a modern, slouchy beret. This red knit number from Ugg Australia will keep you warm, cozy and chic whether you’re heading out après ski, on your way to work or meeting friends for an evening on the town. Belle, oui?

Ugg Australia slouchy beret, $55

6Oval Face Shape: Play ball

When your face is oval, you can rock pretty much any hairdo, sunglass style or—you guessed it—hat. This season, JCrew is bringing back the classic baseball cap, but the bling on this wine-colored, crystal-embellished wool version will take you from the minors to major league fashionista.

JCrew jeweled baseball cap, $125

7Round Face Shape: Boys on the side

If your face is round, create the illusion of length by reaching for a fedora with a high crown. The tallness of this felt style helps thin your face, while the asymmetrical brim is also slimming. Toss in that flirty floral embellishment and you’ve got a winner. Just don’t let it go to your, uh, head, OK?

August asymmetrical felt fedora, $48

8Round Face Shape: Stop the presses

A round face—one that’s as wide as it is long—benefits from a newsboy style. Cocked to one side, the angle helps slim your face, as does the brim. This camel knit look from Echo is classic, but not at all old-fashioned.

Echo “Nostalgic” newsboy cap, $35

9Square Face Shape: To the brim

Women with square, angular face shapes look lovely in wide-brimmed hats, which help soften a wide jawline. The irregular wire brim on this knitted style flatters your angles, and the ribbon trim adds a little femininity to boot.

Perika wire brim hat, $68

10Square Face Shape: Head case

Balance out your strong, square face with a trilby—a soft, felt hat with a narrow brim and indented crown. Catarzi’s wool version features a short brim, velvet trim and pinched crown that gives a nod to menswear—but in a really pretty way.

Catarzi for Asos trilby, $62

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