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Fall & Winter Hats

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.

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New

Bailey Nesbit Baseball Cap with Earflaps

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...
$74.99
New

Bailey Cassell Wool Blend 8 Panel Baker Boy Cap

Textured and timeless, the Bailey Cassell is an 8-panel cap tailored from a soft wool blend in a classic herringbone. The eight-panel crown gives...
$69.99
New

Bailey Penner Wool Blend Five Panel Flat Cap

Clean lines and cool-weather comfort define the Bailey Penner, a contour five-panel cap cut from a soft wool blend in a subtle check. The...
$84.99
New

Bailey Wilsey Wool Trapper Hat

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...
$99.99
New

Bailey Tullio Wool Flat Cap

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...
$124.99
New

Bailey Jeno Lambswool Flat Cap

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...
$124.99
New

Bailey Ciro Shetland Wool 8 Panel Cap

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...
$124.99
New

Bailey Cyd Wool Felt Wide Brim Fedora

Broad-brimmed and effortlessly cool, the Bailey Cyd pairs a 4½-inch raised-front teardrop crown with a wide 3-inch flat brim for a look that leans...
from $149.99
New

Bailey Criss Polished Wool Felt Fedora

A refined everyday classic, the Bailey Criss is a polished wool felt fedora shaped by a 4-inch long teardrop crown and a 2⅝-inch snap...
from $169.99
New

Bailey Kisner Wool Felt Wide Brim Hat

Statement-making from every angle, the Bailey Kisner is a stiffened wool felt wide brim built on a tall 5½-inch open crown and a bold...
from $179.99
New

Bailey Maglor Wool Felt Stingy Brim Fedora

Cool-weather dressing gets a classic anchor with the Bailey Maglor, a wool felt fedora shaped by a 4½-inch teardrop crown and a neat 1½-inch...
$74.99
New

Bailey Klaxon Wool Felt Pork Pie

There's an easy confidence to the Bailey Klaxon, a wool felt pork pie built around a round telescope crown and a trim 2-inch brim....
$74.99
New

Bailey Messie Litefelt Wool Fedora

Character in every angle — the Bailey Messie brings a rich, mottled swirl finish to a sharp center-dent silhouette. Its 4-inch center dent crown...
$159.99
New

Bailey Lionel Litefelt Wool Fedora

Laid-back and effortlessly cool, the Bailey Lionel keeps things low and easy. A 4-inch low profile pinch front crown pairs with a trim 2½-inch...
$174.99
New

Bailey Lasham Litefelt Wool Fedora

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...
$159.99
New

Bailey Sperling Litefelt Wool Fedora

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...
$184.99

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Most Popular

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