winter hats

Don’t let sub-zero wind chills and winter weather keep you from looking your very best. It’s never been easier to bundle up for the elements in style thanks to today’s chic layers and cold-weather accessories. We’re taking a look at some of the cutest and comfiest headpieces for the season, from classic winter hats and fuzzy earmuffs to modern headbands in the coziest knit blends.

7 Winter Hats and Headpieces to Keep You Warm While Looking Cool

1. Charming Charlie Lurex Cloche Hat, $18

winter headpieces

There’s something particularly elegant about a retro-inspired cloche, like you just stepped out of an old black-and-white film with a vintage suitcase in hand. It’s romantic, a bit whimsical, and totally sophisticated — which is a rare combination these days. This affordable design by Charming Charlie features a feminine velvet bow for a modern touch of luxe.

2. Sole Society Lightweight Wool Beanie, $24.95

winter hats

Can we all agree that the athleisure trend needs to stay popular forever and always? Just like your favorite joggers and hoodies, the basic beanie is a style essential that you’ll wear on a regular basis. Pair this everyday hat with a tailored wool coat for a work-ready ensemble, or keep it casual with a parka or utility jacket. This blush-colored Sole Society design goes with anything and everything in your closet, and its slouchy silhouette looks especially pulled together when worn with a matching scarf.

3. Ebbets Field Flannels for J.Crew Brooklyn Eagles Ball Cap, $49.50

baseball cap

Baseball caps are the quintessential headpiece for sporty gals, and they’ve gained increasing popularity among street-style fashion bloggers over the last couple of years. Plus, they come in especially handy on bad hair days. Shop this made-in-the-USA style at J.Crew.

4. J.Crew Factory Faux-Fur Earmuffs, $24.99

winter earmuffs

Maybe it’s because of Princess Leia’s iconic side-bun hairdo in Star Wars. Maybe it’s because of Chanel No. 3 on Scream Queens. Honestly, it doesn’t matter. Earmuffs are always a fashion do, and this fuzzy pair by J.Crew Factory is a winter must-have.

5. Sole Society Ribbed Wool Headband, $24.95

winter hairpiece

No time to create a fancy Pinterest braid? Add a little woven texture to your hair with a wool headband instead. This twisted design by Sole Society is a great way to pull your hair out of your face while keeping your ears warm, and it works with ponytails and long layers alike.

6. Charming Charlie Colorblock Floppy Hat, $22

floppy winter hat

A floppy wool hat is a great way to pull together a casual outfit and give it a little more oomph. Try an earthy neutral hue for the most styling possibilities, or go for a colorblocked brim for a fresh approach that works so well with mixed prints (like this olive-and-black combination by Charming Charlie).

7. Charming Charlie Tres Chic Pom Beret, $18

buy beret online

There’s something about a beret that reminds me of… Confessions of a Shopaholic, of course. This pom-pom design by Charming Charlie is absolute perfection and would totally impress The Girl in the Green Scarf with its style and its price. Enough said.

Which of these winter hats and headpieces tops your wish list? Share your picks with us in the comments section below!