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.
$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
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.”