Best Hairstyles For Winter Hats

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.