Fall Hats

Fall hats are the ultimate finishing touch for your fearless fits, babe. Whether you’re channeling mysterious main character energy or just wanna top off your look with a little extra flair, these styles bring major attitude to every outfit. From spontaneous coffee runs to late-night adventures, fall hats have your back—serving up confidence and keeping your vibe strong wherever you go. Ready to turn heads? Let’s crown that gorgeous hair and own every moment.

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Windsor Kangol Faux Fur Trim Trapper Hat in Black

$84.90

A black wool-blend trapper hat featuring plush faux fur trim, ear flaps, and signature Kangol embroidery.

Kangol Zebra Print Faux Fur Bucket Hat in Olive

$79.90

A plush olive green bucket hat featuring zebra print faux fur, satin lining, and embroidered logo detailing.

Windsor Kangol Corduroy Bucket Hat in Denim

$64.90

A denim blue corduroy bucket hat with classic Kangol logo embroidery and soft cotton construction.

Kangol Faux Fur Shearling Bucket Hat in Black

$79.90

A cozy black faux fur shearling bucket hat featuring a fleece-lined flap and signature front logo embroidery.

Off Duty Faux Leather Cabby Hat in Black

$18.90

A black faux leather cabby hat featuring a round top, seam accents, and an adjustable interior fit.

Windsor Countryside Chic Buckle Strap Cowboy Hat in Black

$25.90

A black cowboy hat featuring a structured top, curved brim, and an etched buckle strap for western flair.

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Windsor Sorry I'm Late, I Stopped For Coffee Baseball Cap in Brown

$12.90

(3)

The perfect baseball cap for all coffee lovers! This adorable hat features an embroidered script reading, "sorry I'm late, I stopped for coffee," and includes a back adjustable strap with a metal buckle. Fit & FeaturesClassic baseball cap design, Round top, Curved brim, Embroidered script reading, "sorry I'm late, I stopped for coffee", Back adjustable strap with metal buckle, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Sorry I'm Late, I Stopped For Coffee Baseball Cap in Brown

Windsor Cold Girl Classic Faux Fur Bucket Hat in Black

$22.90

(1)

Fuzzy, fabulous, and unapologetically extra. This faux fur bucket hat brings that cozy-luxe vibe to any outfit—perfect for layering up, heading out, or just serving “don’t mess with my winter aesthetic” energy. Fit & FeaturesPlush faux fur exterior, Adjustable inner strings for a snug fit, Classic bucket hat silhouette, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cold Girl Classic Faux Fur Bucket Hat in Black

Off Duty Faux Leather Cabby Hat in Black

$18.90

(1)

Serving effortless cool with zero effort—this faux leather cabby hat pulls your whole look together in seconds. Perfect for when you want that model-off-duty vibe without even trying. Fit & FeaturesFaux leather material, Round top, seam accents, button detail, Short curved brim, Woven lined interior, Interior adjustable strings, How To Style For Spooky Season:Pair with a sleek bodysuit and skirt for a fab DIY Halloween look! Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Off Duty Faux Leather Cabby Hat in Black

Windsor Countryside Chic Buckle Strap Cowboy Hat in Black

$25.90

(1)

Enter your western era and look countryside chic in this cowboy hat detailed with an etched buckle strap. Fit & FeaturesStructured top, Curved brim, Thin band, etched buckle, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Countryside Chic Buckle Strap Cowboy Hat in Black

Windsor Low Key Cool LA Baseball Cap in White

$15.90

(1)

Repping the city never looked this effortless. This LA embroidered baseball cap is the laid-back staple you’ll throw on with everything from streetwear fits to off-duty looks. Fit & FeaturesClassic baseball cap silhouette, Structured curved brim, LA embroidered detail on front, Adjustable back strap for a custom fit, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Low Key Cool LA Baseball Cap in White

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Windsor Autumn Stroll Corduroy Baseball Cap in Brown

$6.97 $14.90
53% off

(1)

Laidback but make it luxe—this corduroy baseball cap brings cozy texture and fall-girl vibes to your off-duty fits, perfect for pumpkin patches, PSL runs, and downtown strolls. Fit & FeaturesWide curved brim, Classic baseball cap silhouette, Adjustable back strap, Corduroy material, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Autumn Stroll Corduroy Baseball Cap in Brown

Windsor Cold Girl Classic Faux Fur Hat in Beige

$25.90

Meet your winter style flex. This faux fur ushanka hat keeps you extra warm while serving major vintage ski-glam energy—soft, plush, and ready to make every cold-weather outfit look effortlessly luxe. Fit & FeaturesUltra-soft faux fur exterior, Classic ushanka silhouette, Quilted woven lining, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cold Girl Classic Faux Fur Hat in Beige

Windsor Gloria Cap Sleeve Tie Back Mermaid Formal Dress in Navy Blue

$69.90

(1)

The Gloria formal dress is your effortlessly elegant plus-one, designed in a mermaid silhouette with a bold open tie back that makes every head turn! Fit & Features:Smooth knit fabric with stretch, stretchy knit lining, Square neckline, padded bra cups, Cap sleeves, Open tie back design, lower zipper and hook-eye closure, Mermaid silhouette, Floor-length hem, Runs true to size, Where to Wear:Weddings, black tie galas, formal parties and events, engagement parties, rehearsal dinner, fancy date nights, nights at the theatre, school dances Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Gloria Cap Sleeve Tie Back Mermaid Formal Dress in Navy Blue | Size: XS | Knit Fabric

Windsor Cool Girl Cozy Faux Fur Bucket Hat in White

$18.90

Equal parts cozy and cool, this faux fur bucket hat turns any outfit into a moment. The plush texture and effortless shape make it your go-to for chilly coffee runs and everyday styling. Fit & FeaturesBucket hat silhouette, Ultra-soft faux fur material, Soft lining, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cool Girl Cozy Faux Fur Bucket Hat in White

Cold Girl Era Faux Fur Trapper Hat in Ivory

$32.90

Snow-day vibes, but make it chic. This faux fur trapper hat brings warmth and attitude with a plush texture and cozy ear flaps that make bundling up actually feel like a style moment. Fit & FeaturesSoft faux fur exterior and lining, Trapper silhouette with ear flaps, Adjustable buckle strap, Stylish looks perfect for video calls, virtual meetings, happy hours, e-dates, and remote work from home. Free Shipping on All Orders Over $75. | Windsor Cold Girl Era Faux Fur Trapper Hat in Ivory

Fall Hats

Let’s be real, there’s something utterly iconic about topping off your look with the perfect hat—especially when the air gets a little crisp and your coffee order suddenly comes with cinnamon sprinkles. Hats aren’t just accessories, babe, they’re a whole vibe. Whether you’re channeling mysterious movie star energy with a wide-brimmed felt number, or you’re all about that effortlessly cool Windsor cowboy hat that makes every outfit look like you just stumbled out of a music video, the right hat is your ticket to main character status. Picture this: you’re strutting through the city, leaves crunching under your boots, and your hat is doing all the talking. Maybe you’re headed to brunch with your girls or sneaking away for a weekend road trip—whatever your adventure, a Windsor hat is your trusty sidekick, keeping you cozy, cute, and ready for whatever the day throws your way.

When you’re picking out Windsor hats for your collection, think about your personal style and what makes you feel unstoppable. Are you the queen of oversized sweaters and ankle boots? A classic fedora or a chic beret is basically your soulmate. More of a free spirit who lives for concerts and spontaneous road trips? A Windsor cowboy hat is practically made for you—just add your favorite denim and a little bit of attitude. And let’s not forget, hats are the ultimate gift for your ride-or-die bestie, your trendsetting sister, or even your mom who’s always stealing your style. They’re that rare combo of thoughtful and practical, plus they instantly elevate any outfit, making them a go-to for birthdays, holidays, or just because you want to make someone’s day. Pro tip: stash a few different styles in your closet so you’re always ready for last-minute plans, bad hair days, or those moments when you need a little extra confidence boost.

It’s not just about looking cute (though, let’s be honest, that’s a big part of it)—a great hat is also about comfort, versatility, and making your own rules. Look for details like adjustable bands, soft linings, and textures that feel luxe to the touch. Try on different brim sizes to find your perfect match, and don’t be afraid to experiment with bold colors or playful embellishments. And if you’re in the mood to really level up your accessory game, check out our curated collection of Stylish Hats For Women for even more inspo. Whether you’re dressing up for a night out or keeping it low-key with your favorite jeans, Windsor hats are the finishing touch that says, “Yeah, I woke up like this—and I’m loving every minute of it.”

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Fall Hats

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