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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Kangol Faux Fur Shearling Bucket Hat in Black

$38.97 $79.90 51% off

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

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Kangol Corduroy Bucket Hat in Denim

$31.97 $64.90 51% off

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

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 Cool Girl Cozy Faux Fur Bucket Hat in White

$8.97 $18.90
53% off

(3)

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

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 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

City Cozy Tweed Cabby Hat in Ivory

$16.90

A little vintage, a little cool-girl—this tweed cabby hat is the easiest way to make any outfit feel instantly styled. The textured finish adds that effortlessly polished vibe, even on your most “just grabbed something” days. Fit & FeaturesStructured cabby hat silhouette, Tweed texture material, sewn-in lining, Short curved brim, 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 City Cozy Tweed Cabby Hat in Ivory

Sale

Kangol Faux Fur Shearling Bucket Hat in Black

$38.97 $79.90
51% off

Street style just leveled up—this Kangol shearling bucket hat is equal parts cozy and iconic. With its plush faux fur and signature Kangol logo, it’s the ultimate finishing touch for chill days or statement 'fits. Fit & FeaturesFaux fur shearling material, Side trims, Fleece-lined flap, Knit lining, "Kangol" front embroidery and logo, Runs true to size, 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 Kangol Faux Fur Shearling Bucket Hat in Black | Size: S

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Windsor Cold Girl Classic Faux Fur Hat in Beige

$11.97 $25.90
54% off

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

Sale

Kangol Corduroy Bucket Hat in Denim

$31.97 $64.90
51% off

Low-key iconic—this Kangol corduroy bucket hat gives your outfit that instant cool factor without even trying. The classic Kangol logo keeps it timeless, while the texture adds just the right amount of edge. Fit & FeaturesCorduroy material, Internal cotton seams, "Kangol" front embroidery and logo, Classic bucket shape, Runs true to size, 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 Kangol Corduroy Bucket Hat in Denim | Size: M | Cotton

Lucky Shot Two-Tone Baseball Cap in Black

$16.90

Luck’s on your side. This two-tone baseball cap brings sporty-cool vibes with an embroidered 8-ball design and “Lucky You” lettering—perfect for adding attitude to your off-duty fits. Fit & FeaturesStructured baseball cap design, Two-tone color block paneling, Embroidered “Lucky You” 8-ball graphic, Curved brim, Adjustable snapback closure, 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 Lucky Shot Two-Tone Baseball Cap in Black

Tequila Therapy Embroidered Baseball Cap in Brown

$16.90

A cap with a sense of humor — this embroidered baseball hat brings that carefree, sun-on-your-shoulders kind of energy. Easy to throw on, easy to style, and even easier to relate to. Fit & FeaturesClassic baseball cap silhouette, Embroidered “life happens tequila helps” text, Curved brim design, Adjustable back 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 Tequila Therapy Embroidered Baseball Cap in Brown

Caffeinated And Cute Snapback Hat in Brown

$16.90

A mood and an outfit formula in one. This embroidered snapback brings cozy caffeine-girl energy with a playful message that pairs perfectly with your messy bun and morning iced latte. Fit & FeaturesSoft structured snapback silhouette, Embroidered “more espresso less depresso” text, Curved brim design, Adjustable snapback closure, 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 Caffeinated And Cute Snapback Hat in Brown

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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