Casual Hats

Casual hats are your go-to move for leveling up any laid-back look with zero effort. Whether you’re dodging a bad hair day or just want to add a little extra attitude, these chill toppers have your back every time. Throw one on for instant cool-girl energy—because let’s be honest, you were never meant to blend in. From coffee runs to spontaneous road trips, casual hats are the ultimate partner-in-crime for every adventure that comes your way.

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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.

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.

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.

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.

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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

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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

Casual Hats

Casual hats are the ultimate finishing touch—the exclamation point on your outfit, the wink in your selfie, the “I woke up like this” energy you can actually wear. Whether you’re living for lazy brunches, spontaneous road trips, or just keeping it low-key cute on a coffee run, a great hat is your bestie in disguise. She’s there to hide your second-day hair, keep the sun off your flawless face, and turn a basic tee-and-jeans combo into a full-on vibe. From the classic slouch of a bucket hat to the effortlessly cool tilt of a windsor cowboy hat, there’s a style for every mood, every plan, and every “oops, I’m running late” moment. When you’re picking out your new favorite, think about the details that make you feel like *that* girl: a playful brim, a pop of color, or a texture that begs for a double-tap on your feed. And let’s be real—windsor hats aren’t just for you. They’re the kind of gift that says “I see your style, and I’m obsessed,” making them perfect for birthdays, bestie swaps, or just because you want to be the friend who always gives the best surprises.

What makes casual hats so iconic is their chameleon energy. One minute, you’re channeling main character energy in a cowboy hats windsor moment, the next, you’re giving “mysterious girl in the corner” with a wide-brimmed windsor hat pulled low. Heading out for an impromptu picnic? Grab a floppy hat and a blanket, and you’re basically living in a rom-com montage. Or, if you’re catching up with your squad for golden hour rooftop hangs, a crisp baseball cap or a windsor cowboy hats fit can take your look from “just rolled out of bed” to “effortlessly put together” in literal seconds. And if your calendar is packed with summer adventures, don’t sleep on the practicality factor—hats are the low-key MVPs for protecting your glow, keeping you cool, and making sure your makeup stays on point, no matter how high the temps climb. Even if your style is more minimalist, adding a statement hat can be the one accessory that flips your whole look from “cute” to “can’t stop staring.” And if you’re a collector (no shame, we see you), building a lineup of windsor hats means you’re always ready for whatever the day throws your way, from spontaneous beach days to late-night drive-thrus.

If you’re ready to take your accessory game to the next level, don’t forget to explore the rest of the must-haves that make every outfit pop. From bold sunglasses to stackable jewelry and everything in between, you’ll find all the finishing touches that let you express your style, your way. Check out our curated edit of Casual Accessories to keep your looks fresh, fun, and totally you—because life’s too short for boring outfits, and your hat game deserves to be legendary.

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