When temperatures drop, the right hat keeps you warm without sacrificing style. Our fall and winter hats collection brings together cold-weather essentials — wool felt fedoras, cozy knit beanies, tweed flat caps, fur-felt western hats, and earflap trappers — from trusted makers like Stetson, Bailey, and Kangol. Whether you need everyday warmth or a polished finish for the season, you'll find a men's or women's winter hat built to handle the chill.
Cold-weather practicality meets everyday ball-cap ease in the Bailey Nesbit. Cut in a classic six-panel baseball shape with a structured 2½-inch peak, it's finished...
When the temperature drops, the Bailey Wilsey has you covered. This cold-weather trapper pairs a 100% wool shell with plush faux-fur-lined earflaps, so you...
A wardrobe staple done right, the Bailey Tullio is a classic flat cap tailored from 100% wool. Its clean, low-profile shape and distinguished stitched...
Tailored and textural, the Bailey Jeno is a five-point flat cap cut from luxuriously soft lambswool in an understated check. The five-panel construction sews...
Old-world charm meets everyday ease in the Bailey Ciro, an 8-panel cap cut from soft 100% Shetland wool. The eight-panel construction gives the crown...
A snap-brim classic done right, the Bailey Lasham is an everyday fedora with clean, confident lines. Its neat 3½-inch diamond crown and versatile 2½-inch...
Easygoing and endlessly wearable, the Bailey Sperling is a low-profile fedora that fits right into daily rotation. A 4-inch low profile pinch front crown...