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.
$16.90
A structured ivory cabby hat crafted from textured tweed with a short curved brim and sewn-in lining.
$16.90
A brown snapback hat featuring embroidered “more espresso less depresso” text and an adjustable closure.
$13.90
A classic black woven felt beret featuring a soft structured crown for an effortlessly polished look.
$16.90
A structured beige cabby hat crafted from soft faux wool for a polished, effortlessly styled look.
$16.90
A chic black cabbie hat featuring a rhinestone bow and faux leather brim for standout style.
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Fit & FeaturesFaux wool material, Rhinestone embellished bow decoration, Faux leather 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 Glam In The City Rhinestone Bow Cabbie Hat in Black-2 | Leather/Rhinestone
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
Say less, wear more confidence. This embroidered hat finishes off casual looks with an effortless attitude that feels intentional, not try-hard. Fit & FeaturesSoft cotton fabric with structured feel, Classic baseball cap silhouette, Curved brim for everyday wear, Front embroidered Hotter Than Ever text, 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 Hotter Than Ever Baseball Cap in Burgundy | Cotton
For the days you want your outfit to speak first, this cap handles the intro. The structured two-tone design and bold "Favorite Girl" embroidery make it the easiest confidence boost you can throw on. Fit & FeaturesStructured two-tone design, Bold “Favorite Girl” front embroidery, Classic six-panel construction with stitched eyelets, Curved brim, Adjustable snapback closure for a customizable 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 Favorite Girl Two-Tone Baseball Cap in Black
Coastal cowgirl is calling. This woven straw cowboy hat features a shell-trim band with subtle rope detail, giving beachy energy with a western twist—perfect for vacations, festivals, or sunny day styling. Fit & Features Seashell trimmed band with string tie, Wide curved brim, Classic cowboy hat silhouette, Straw 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 Seaside Rodeo Shell Cowboy Hat in Khaki
Easy, effortless, and made for sun-soaked days. This woven straw cowboy hat features a breezy open weave and a braided tie with fringe detail for that laid-back western vibe that goes from beach to festival without missing a beat. Fit & FeaturesStraw material, Structured cowboy hat silhouette, Open weave design, Braided tie detail with fringe ends, Curved wide 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 Weekend Escape Straw Cowboy Hat in Khaki
Serving boho cowgirl energy with a hint of wanderlust. This straw cowboy hat features an intricate woven design and a standout beaded band with turquoise detail for that effortlessly styled, sun-chasing look. Fit & FeaturesWoven straw material, Structured cowboy hat silhouette, Intricate open weave design, Beaded band with colored accents, Curved wide brim, tea-stained finish, 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 Wander West Beaded Cowboy Hat in Brown
Country core, but make it cool. This statement cowboy hat features a tea-stained finish with a bold longhorn accent that pulls every look together—from festivals and concerts to country line-dancing nights! Fit & FeaturesWoven straw material, Structured cowboy hat silhouette, Curved wide brim with tea-stained finish, Faux leather band with longhorn inset, 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 Dust Trail Longhorn Cowboy Hat in Brown | Leather
This distressed cowboy hat brings serious outlaw energy with its worn-in texture and classic curved brim silhouette. The perfect finishing touch for festival looks, bachelorettes, or any outfit that needs a little country attitude. Fit & FeaturesDistressed texture, Classic cowboy hat silhouette, Wide curves 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 Midnight Outlaw Distressed Cowboy Hat in Black
This snake print cowboy hat adds instant attitude to your outfit, whether you're heading to a concert, festival, or just leaning into your western era. Fit & FeaturesClassic cowboy hat silhouette, Wide curved brim, Snake print, 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 Wild West Mood Snake Cowboy Hat