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.

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U Know the Vibes Miami Trucker Hat in White

$3.97 $16.90 77% off

A white mesh trucker hat featuring "Miami" embroidery, breathable panels, and an adjustable snap-back design.

Windsor 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 embroidered logo.

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.

Sale

Windsor Gone Country Snap Back Hat in Black

$7.97 $15.90 50% off

A black two-tone snapback hat featuring embroidered "Gone Country" script and an adjustable closure.

Windsor Kangol Corduroy Bucket Hat in Denim

$64.90

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

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Big Fan Energy Florida State® Trucker Hat in Burgundy

$3.97 $16.90 77% off

A burgundy trucker hat featuring mesh panels, front embroidery, and an adjustable snap-back design.

Windsor Glam Western Vibe Rhinestone Buckle Strap Cowboy Hat in Brown

$26.90

A brown faux wool cowboy hat featuring a curved brim and a rhinestone-embellished buckle strap.

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 Western Sun Micro Suede Cowboy Hat in Ivory

$24.90

An ivory micro suede cowboy hat featuring a wide curved brim and adjustable inner strings for comfort.

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.

Windsor Starlight Rodeo Cowboy Hat in Ivory

$25.90

An ivory cowboy hat featuring metallic studs and sparkling star accents for a bold, cosmic-inspired look.

Windsor Western Babe Heart Concho Trim Cowboy Hat in Silver

$26.90

A silver faux suede cowboy hat featuring a heart concho chain-link trim and a wide curved brim.

Windsor Wild Spirit Beaded Straw Cowboy Hat in Khaki

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Windsor Wild Spirit Beaded Straw Cowboy Hat in Khaki

$12.97 $26.90 52% off

A khaki straw cowboy hat featuring a beaded trim, turquoise accents, and a curved wide brim.

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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 Glam Western Vibe Rhinestone Buckle Strap Cowboy Hat in Brown

$26.90

(3)

Glam up your western vibe with this trendy cowboy hat featuring a structured top, a curved brim, and a thin strap with a sparkly rhinestone-embellished buckle. Style with rhinestone hoop earrings! Fit & FeaturesFaux wool material, Structured top, Curved brim, Inner adjustable strings for a snug fit, Strap with rhinestone 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 Glam Western Vibe Rhinestone Buckle Strap Cowboy Hat in Brown

Cozy Glam Faux Fur Round Bucket Hat in Black-2

$19.90

(2)

Fit & FeaturesFaux fur fabrication, Round top, Wide contrast brim, CW: FAUX FUR ROUND TOP BUCKET HAT (073021661001) 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 Cozy Glam Faux Fur Round Bucket Hat in Black-2

Windsor Cozy Luxe Faux Fur Bucket Hat in Brown

$22.90

(1)

Cold days just got a glow-up. This faux fur bucket hat adds instant glam to any outfit—serving cozy vibes with a side of it-girl energy. Fit & FeaturesSoft faux fur material, woven lining, Plush texture with luxe feel, 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 Cozy Luxe Faux Fur Bucket Hat 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

Windsor Autumn Stroll Corduroy Baseball Cap in Brown

$14.90

(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

Western Blooms Embroidered Rose Cowboy Hat in Brown

$25.90

(1)

Bring the romance to the West in this cowboy hat with pretty embroidered roses, perfect for sweetening your look for concerts or festivals! Fit & FeaturesEmbroidered roses, Wide curved brim, Inner adjustable strings for a snug 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 Western Blooms Embroidered Rose Cowboy Hat in Brown

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

Western Adventure Faux Suede Cowboy Hat in Ivory

$25.90

(1)

Charm with Western flair in this faux suede cowboy hat with a unique stitched pattern band accented with studs and a tie-back detail that sets you apart from the crowd! Fit & FeaturesStitched pattern band, stud accents, tie-back detail, Wide curved brim, Faux suede material, Inner adjustable strings for a snug 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 Western Adventure Faux Suede Cowboy Hat in Ivory

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

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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