Bold for the Cold: 2025’s Best Hats for Men and Women

Find the hottest trending hats for men and women as you prepare for the cold.

When the temperatures start to decrease, it’s time to get out the wishlist for warm winter accessories. This year’s best hats feature the chunkiest knitwear and fluffiest poms. Staying warm has never looked this good with fashion houses like Miu Miu and Chloe influencing global shopping carts with a fantastic range of accessories to round out your fall wardrobe. 

Hats for men and women pull double duty as fashionable and functional accessories, keeping your head warm, with endless structures, styles, and materials to make a personal fashion statement. This year, we’re seeing revived interest in sleek beret, cap, and pillbox styles, with more contemporary classic looks for men's hats. If it’s time to prepare for the cold, we’ve rounded up some of our favourite winterwear, inspired by the trending styles of 2025! 

Hats for Men: Dubliner by Hatman of Ireland 

With an unlimited array of options for what a hat could look like–floppy, structured, velvet, woo- Hatman of Ireland opts for whimsical hues inspired by the Irish countryside. The quilted lining brings extra warmth to this expertly crafted piece, woven from 100% Donegal Tweed in a herringbone pattern. As a fitted flat cap currently available in brown, green, and grey, Dubliner is a contemporary piece that will never go out of style. 

Hats for Women: Wool Classic Lauren by Lillie and Coho 

Sleek and asymmetrical, crafted from a luxurious cashmere blend in winter-inspired jewel-tones, Wool Classic Lauren grants a stunning asymmetrical silhouette. The crown wraps neatly around the head for a compact silhouette, yet the design remains playful. Designed and made in Canada, Lauren is crafted from 90% wool, with a touch of cashmere for warmth and softness–perfect for all your winter activities. 

Hats for Everyone: Brood Snapback by Brixton 

Brixton is always at the edge of accessory style, and one of the perennial favourites is Brood Snapback. Vintage-inspired, this sleek piece is one of the hatmaker’s signature silhouettes. Updated in a range of colourful options like navy plaid and sandstone, this neat cap provides the perfect juxtaposition to the season’s broad, flowing silhouettes. 

Hats for Women: Cici Ormos by Canadian Hat

Crafted from European soft-boiled wool and a fluffy upcycled fur pom, Cici is one of our most luxurious hats on this list. Available in shades of black, charcoal, green, and heather, Cici is close-fitting and inspired by the silhouettes of the 1920s. If your objective is one perfect fall accessory to elevate your winter wardrobe, this might be it. 

Hats for Men: Gottmann Jackson K-G Cap 

As a curved-style winter cap, Gottman is a men’s brand that seamlessly blends form and function. Jackson’s rounded, form-fitting shape inspires a chic yet casual look. As fashion leans into more traditional styles in 2025, German-made Gottman remains a name synonymous with high-quality materials, expert workmanship, and attention to detail. Jackson blends premium wool and a Gore-Tex lining for a feel-good accessory that handles all kinds of wintery weather. Complete with tuckaway earflaps for extra protection on the coldest days. 

Step into Style This Winter–Only at Roxann's Hats!

Discover our exclusive winter collection – cozy, chic, with many styles not available online. From elegant wool cloches to bold statement pieces, we’ve got so many beautiful new styles waiting for you in-store only. Come in now to see our best selection.