The Fashionable Winter Hat

Styling winter hats doesn’t have to mean sticking to the classic beanie or wool hat—though they’re always cozy go-tos. Why not elevate your look with some stylish alternatives? A cloche hat, with its close-fitting, vintage-inspired silhouette, adds timeless elegance. A bucket hat offers playful functionality with its soft structure and wide brim. For bold sophistication, try a pillbox hat, known for its structured, minimalist design often accented with embellishments. A fur hat, like a trapper or ushanka, adds luxurious warmth and texture. A wool baseball cap combines casual comfort with a polished edge, while a wool beret lends Parisian charm with its soft, slouchy silhouette. These options let you stay warm while making a chic statement all winter long.

Fashionable Winter Hats

8 Looks

If you were inspired by all of the hats at the Inauguration, might I suggest this hat from Gigi Burris, a celeb favorite - it's definitely a fashion moment, and not your typical hat - however if you attend formal events - this is a great addition to your collection.

A softer beret creates a casual look with ease, while keeping your head warm, and adding polish to a casual look.

A winter tweed baseball cap is a great way to tie in the winter season to your look. The tweed is eye catching, with any simple outfit - in this case chocolate brown trousers, and coordinating cream pieces.

A cloche style hat is always sophisticated and in style. Pair with a Leopard coat, and black dress for a night out on the town. You can easily wear a white t shirt and jeans with this look too.

Inspired by Kendall Jenner's latest look in Aspen, this cozy hat will keep you warm and looking fashionable. Copy her look by wearing leggings, riding boots, and a fitted blazer. You can also wear this hat with any of your favorite winter coats to add visual interest.

Post hot yoga, or pilates, throw on a knit beanie or this cool shawl/scarf hooded combo to stay warm after class. If you are running errands - this is the perfect piece to keep your hair looking great, while staying warm at the same time.

The wool bucket hat - this hat will add sophistication to any classic outfit, and is the perfect topper to wear out to dinner, or a fancier daytime outing. You can wear this hat dressed up or down, and will add polish to any look.

Wearing a beret is always in style, and is a nice way to create polish to a classic outfit. Whether you are choosing the designer option, or a cashmere beret, this structured version is sure to make a statement with any look.