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.
$25.90
A flirty denim cowboy hat featuring stitching detail, a structured top, and a wide curved brim.
$24.90
An ivory micro suede cowboy hat featuring a wide curved brim and adjustable inner strings for comfort.
$25.90
A black cowboy hat featuring embroidered roses and an adjustable fit for stylish festival looks.
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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
Giddy up, glam girl—this cowboy hat is serving country with a side of chaos. Perfect for festival fits, photo ops, or spontaneous yeehaw moments. Fit & FeaturesWide curved brim, Faux suede 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 Ride or Slay Cowboy Hat in Black | Faux Suede
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
For the girl who runs on caffeine and compliments. This embroidered baseball cap is your grab-and-go essential for coffee runs, casual hangs, and bad hair day cover-ups. Fit & FeaturesCurved brim, Embroidered “Running on Coffee and Good Vibes” front, Adjustable back strap 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 Running On Coffee Baseball Cap in Brown
She’s got rodeo dreams and main stage energy. This denim cowboy hat is the flirty finishing touch your outfit’s been waiting for—perfect for festivals, weekend plans, or anytime you’re feelin’ yourself. Fit & FeaturesDenim material, Stitching detail, Structured top, Wide 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 Howdy Hottie Denim Cowboy Hat
Rodeo Romping Lace-Up Cowboy Hat in Ivory
$12.97 $26.90
52% off
Show off your Western flair in this faux suede cowboy hat with lace-up detailing that turns heads and a wide, curved brim that shades your eyes! Fit & FeaturesLace-up detailing, Wide curved brim, Faux suede 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 Rodeo Romping Lace-Up Cowboy Hat in Ivory | Faux Suede
Embrace Western charm and the sun in this cowboy hat. Crafted from soft micro suede, this hat offers a comfortable fit while adding a touch of rugged style to any outfit. Fit & FeaturesMicro suede material, Structured top, Wide curved brim, Adjustable inner 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 Sun Micro Suede Cowboy Hat in Ivory
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: M | Knit Fabric
Achieve a cool and laid-back vibe with this trucker hat, where state pride meets unbeatable style. Featuring a wide curved brim and a bold Texas embroidered script, and an adjustable snap back closure for the perfect fit. Fit & FeaturesWide curved brim, Embroidered Texas script, Two-tone design, Snap back adjustable 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 Texas Snap Back Trucker Hat in Red
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 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.