The On-Trend Hats and Caps to Try This Season

Image via Anthropologie

Along with scarfs, vests and jackets, winter is all about mastering the layered look. Depending on your fashion sense, the crossover to boots and beanies can take a (hot) minute. And by hot, I mean cold (very cold). Because there is nothing worse than the tip of your nose and the top of your ears feeling the freeze in Feb, the following is a list of add-ons to make it through the season.

From furry to fuzzy (and everything in between), the on-top touch has transitioned from a necessary for shoveling the street and sidewalk to an accessory for pulling off fashion forward fun. To achieve the layered look and textured type from head to toe, check out this product round up of hats & caps to pick up and try on.

Saddle Up and Ranch On

Anthropologie: Teak Rancher

With a broad rim and leather trim, this classic rancher elevates any outfit of the day (OOTD) with stylish ease. While you’re crossing your fingers for some sun, top off the look with a pair of winter-wear shades. And keep it casual and comfy by sticking with the color black.

A Nightcap (or Two)

Zara: Check Cap

Zara: Plaid Skipper Cap

So, you don’t cheer for a (winning) baseball team or follow the sport? No biggie. It doesn’t mean you can’t sport a cap on repeat.

On first base, the navy blue check cap with visor offers a fashionable twist on the traditional cap and an adjustable closure.

On second base, the taupe brown skipper cap with visor shares the same feels as “the old man sweater” in all the right ways. As noted online, this accessory is the perfect match for a block heel leather boot.

Flip It and Flop It

rag & bone: Floppy Brim Fedora

Described as a foolproof fedora with a flexible brim, this hat is 100% wool body and available in three different sizes (small, medium and large). While wearing this beauty, there’ll definitely be no ragging on your fashion sense.

It’s All Beanie Baby

Free People: Game Changer Beanie

Feel free to add a punch of color to your winter blues by changing up your fashion game. Available in bright, bold & beautiful colors, this classic knit beanie features a stretch fit and slouchy ribbed design with a folded headline. No need to take part in board game night with your friends and fam, you’re already a winner.

French Connection: Rib Pom Pom Beanie

Since it’s agreed that one beanie per closet is one too less and choosing a non-pom is a winter no-no, keep it plain and simple with this super soft wool blend knit with a fur feature. Tip of the day: cold hand wash separately.

Icy Igloo Feels

Overland: Spanish Shearling Sheepskin Convertible Trapper Hat

When function combines with fashion. Defined as the world’s warmest headgear, genuine sheepskin protects from “bitterly cold” sweater weather. With a versatile three-in-one design, this trapper offers convertible side ear flaps (to be worn up or down) and a detachable chinstrap that stores easily on the back of the hat.

Somewhere Between French Flair and Big Brim

ASOS: ASOS Design 90s Beret

ASOS: Stradivarius Bucket Hat with Ties

Whether searching for a trendy beret or bucket hat, ASOS is on point. Throw it back or bucket up for a solid winter style ride.

A Hard Pass on Hat Head

H&M: Knit Headband

To avoid hat head or cover up a bad hair day, opt for a headband. From forest green to mustard yellow, this double-layered accessory offers all of the normal neutrals to make matching in the morning easy as grab and go. The knot detail at the front of the band allows for maximum warmth.


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