How to Style Your Hair With Winter's Best Hats

Every cute hat has its hair challenge.

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If You're Wearing a Baseball Cap...Try a Side Braid!

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Faux Fur Baseball Hat, $45, openingceremony.com; The E2 Stretch Turtleneck, $35, everlane.com.

You don't have to choose between your favorite snapback and Snap-ready hair. Turn that hat around, shift your braid from back to front, and suddenly it all works. "We did a loose French braid on the side that turns into a fishtail braid," hairstylist Stacey Ciceron says of this look, which she created specifically for backwards-baseball-cap days. "I pulled it apart a little bit, but not too much—you don't want the layers to fall out."

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Pro tip: If your hair is on the fine side, try prepping it with styling pomade, like Paul Mitchell's Dry Wax ($19, available in professional salons only; paulmitchell.com for locations). According to Ciceron, "it'll give your hair a good grip for braiding."

Or a Low Bun!

Bo Hat, $148, eugeniakim.com; Turtleneck, H&M.

Ponytails and baseball caps are a no-brainer; why not go the unexpected route with a sleek, low bun? To get started, remove any tangles with a large paddle brush. "Natural boar bristle is great for maintaining shine and keeping flyaways and frizz under control," Ciceron says.

Next, mist your hair with a flexible-hold hair spray, like Amika's Touchable Hairspray ($23, loveamika.com), secure it with an elastic, and twist it into a little doughnut (you'll probably need three or four bobby pins here). Now lock everything down with one last hair spray spritz, and go make the most of your good hair day.

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Yes, Beanies and Bangs Can Peacefully Coexist

Tallulah Beanie, $207, eugeniakim.com; Shiny Bomber Jacket, $55, topshop.com.

When it comes to styling your hair with a beanie, wisps (or, as Ciceron calls them, "personality pieces") are key. The face-framing strands "add a little life and fun," she says. To recreate this look, brush your hair back into a low ponytail, then free a few pieces; if you have bangs, separate them with a deep part, do a side swoop, and set them in place with hair spray.

"As your forehead gets oily, your bangs tend to draw together, and hats only make the problem worse," Ciceron says. "Dry shampoo will absorb some of those oils and give your bangs that fluffier look." Stash a travel-size can in your bag for touch-ups; Klorane's Dry Shampoo with Oat Milk ($10, sephora.com) is basically magic.

Wide-Brim Hats Look Great with Undone Waves

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Hat, Zara; Chambray Shirt, NLST.

Structured hats, like this wide-brim Zara style, can look laid-back; just keep your hair loose and wavy. If your hair is naturally straight, fake some texture by blasting it with sea salt spray, like Redken's Fashion Waves 07 ($20, ulta.com). Then, apply a mist of flexible-hold hair spray, and start wrapping sections around a one-inch curling iron.

"For a natural look, make sure not to curl your hair from root to tip; stop an inch or two before you reach the ends," Ciceron says. "I also like to alternate curls—some forward, some backward—it'll give the style extra fullness."

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And Dutch Braids!

Velour Round Crown Hat by Hat Attack, $89, intermixonline.com; The Luxe Wool Ribbed Turtleneck, $88, everlane.com.

Dutch braids are practically indestructible, which makes them perfect for hat days. Again, if your hair is super-straight, a touch of styling pomade will give you some extra hold. This style looks great with or without bangs; if you don't feel like dealing with yours, just sweep them away from your face and lock them down with hair spray.

Earmuffs and Topknots 4Ever

Janine Earmuffs, $172, eugeniakim.com; Oversize Puffer Jacket, $140, topshop.com.

Earmuffs add width to your face, and a topknot balances things out with some height. "I used a little bit of dry wax to brush the hair up—bangs, too!—with my fingers and secured it with an elastic. Then I used some hair spray on the flyaways," Ciceron says. "If you find that you're getting a little too much volume in your topknot, you can use a bobby pin to bring it down." Symmetry has been restored.

Models: Lena Bedoyan and Chen Yu for MSA Models. Hair: Stacey Ciceron. Makeup: Sae-Ryun Song

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