12 Cute Winter Hats That Drastically Outshine Your Boring Beanie

If you're tired of your plain black beanie but keep resorting to it because it's warm AF, it's time to seriously improve your accessories game. There are plenty of cute winter hats that will both keep your head hot and make your outfit about 1,000,000 times cooler, so set that beanie aside and save it for a day on the slopes.

Winter style can start to feel monotonous as soon as wearing a heavy duty jacket every morning is a thing. Covering up with the same wrap day in and day out for months feels sartorially stunting, which is why cool accessories that can amp up a look are such important sources of joy to me. Amazing winter boots, chunky knit scarves, colorful mittens — these things make me so happy, too happy — during cold months. And, of course, fun and decidedly not-boring hats. Beanies are great but they can get old when rocked in typical one-hued form. Choose one with a fun pom pom and rainbow knit material and they get infinitely more exciting. Better yet are toppers boasting an unconventional shape, cool print, luxe texture, or the like, so take a look at the below 12 hats and choose one that makes you look forward to going outside.

Mais Oui

Maharishi Embroidered wool beret




The classic beret gets a cool twist thanks to a structured silhouette, dangling ribbons, and cool print on the top. It's red, white, and black color scheme makes it feel preppy and all kinds of chic.

Sweater Weather

Warm Wishes Beanie




This is what I mean by an exciting beanie. It boasts a super chunky knit fabric that looks softer than an actual baby sheep, while its light blue color scheme and puffy pom pom render it beyond fitting for a winter wonderland. I want to wear this 24/7 — it's like a hug for your head.

The Fuzz

Teddy Hat



Urban Outfitters

It doesn't get better than a peach fleecy hat. This thing looks warm AF and is incredibly cute to boot.

Pink Lady

Faux Fur Newsboy Cap



Opening Ceremony

This faux fur hat embodies peak 2000s style in the best of ways and will undoubtedly make you stand out on any sidewalk.

Mix Master

Rebecca Minkoff Patchwork Jacquard Beanie




The power of pattern mixing should never be underestimated.

Teddy Time

Ginsberg Cap




This hat is my favorite on the list for so many reasons. From its cool brimless structure and orangey brown color to its teddy bear-like texture and ability to make anyone look rad as heck, it is definitely one to add to your wardrobe.


Fairisle Cuff Beanie



Free People

Meet you at the chalet?

Heart To Heart

Federica Moretti Stitched-heart wool military cap



Matches Fashion

Another structured brimless hat, this time finished off with a sweet and subtle pink heart.

British Influence

Anthropologie Wool Engineer Cap




I love that this hat is trending again, and I love this one in particular because it's made of super warm wool.

Kick The Bucket

Sherpa + Suede Bucket Hat



Urban Outfitters

It's a suede bucket hat lined in faux fur. Need I say more?

Hot Headed

Think Royln Downtown Crown with Rib Beanie Hat




Because coats shouldn't get all of the puffy fun.

Très Chic

Margot Slouchy Beret



Free People

For if a regular sized beret isn't dramatic enough for you.