Hairstyles To Wear With Cozy Winter Hats

Of all the First World Problems that vex us, one of the most annoying has to be the quandary of figuring out what to do with your hair under a winter hat. Certain head toppers can look silly or costume-y when paired with the wrong hairstyle (we're still regretting a certain high-ponytail/beanie combo from last year). With winter upon us and our chosen chapeaux begging to be donned, we asked celebrity stylist and Redken brand ambassador Rodney Cutler to break it down for us. Click through to find out which hairstyles go best with winter's chicest hats, plus Cutler's tips for fighting the dreaded hat head.
Photos (clockwise from top left): Via Rail, Via ShopBop, Via JCrew, Via ASOS
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Slouchy Knit
“Since it's a bit of a hipster look, I see playful, messy curls or waves with this hat," says Cutler. "“If you have curly hair, a big woolen hat is best because you can scrunch the hair up inside. When you take the hat off you'll have great curls — the hat becomes your diffuser!" For curly har, add Redken Tousle Whip 04 Soft Texturizing Cream-Wax and twist curls around your fingers. On straight hair, set with a curling iron then pull curls apart to create messy waves.

Paul's Boutique Pom Pom Beanie Hat, $27.27, available at ASOS.

Photos: Via ASOS
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Cloche or Beret
“I envision a girl in a cloche with her hair to one side, offsetting it with a messy bun that sits behind the ear," says Cutler. "Be sure to allow some hair to be seen from the front — this plays up the sort of effortless chic vibe of the Parisian girl who I see wearing this hat." When purchasing a more structured hat, Cutler says to look for one that has a silk lining — dry winter air causes an increase in static and a liner can help reduce this.

Mademoiselle Slassi Soft Focus Cloche, $200, available at BHLDN.

Photos Via BHLDN
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Trapper Hat
“If you’re going to pull this hat off, you should hide the hair entirely — allow the hat to be the total look. Depending on hair length, pin hair into a bun or secure it to the back of the head, and fit the hat over so that no extra hair is showing," says Cutler. If you have extra-long or thick hair and want to show a bit of it off, we also like this hat with a thick braid.

Big Buddha Faux Fur Trapper Hat, $38, available at Nordstrom.

Photos Via Nordstrom
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Knit Headband
"Backcomb the crown to create that exaggerated lift and height at the crown, fit the headband on, and then split your hair around the shoulders so that it falls down on either side. Keep the strands straight but with a little texture for movement,” says Cutler. When wearing your hair down in the winter, moisture is key, so be sure to use a hydrating oil. Cutler recommends applying it to dry or wet hair, smoothing palms over the hair shaft. You can also use this trick to tone down frizz after you remove the hat.

Cheap Monday Crinkle Headband, $30, available at Shopbop.

Photos: Via Shopbop
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“With earmuffs, if your hair is really symmetrical they tend to look like headphones, so I think a puffy ponytail to one side can offset the look," says Cutler. He suggests blowing out hair with a bodifying mousse and backcombing it to create an airy texture. Secure hair into a side ponytail about an inch or two down from the nape of the neck.

Marc Jacobs Fox Earmuffs, $750, available at Neiman Marcus.

Photos: Via Neiman Marcus