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.
$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.
$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.
$13.90
A classic black woven felt beret featuring a soft structured crown for an effortlessly polished look.
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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
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
Bad hair day or just building the look from the top down. This "Bar Star" trucker hat gives effortless cool with bold front embroidery, breathable mesh back, and that off-duty country vibe. Fit & FeaturesStructured curved brim, Classic trucker hat silhouette, "Bar Star" embroidered front script, Snapback closure, Sheer mesh back panel, 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 Backroads Babe Bar Star Trucker Hat in Brown | Sheer Mesh Fabric
Boots on, plans pending—this is the vibe. This bandana print cowboy hat brings a soft statement feel that instantly pulls your whole look into its country era. Fit & FeaturesBandana embossed pattern, Wide curved brim, Structured cowboy hat silhouette, Inner adjustable strings for a snug fit, 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 Out West Plans Cowboy Hat in Beige | Faux Suede
Serving effortless cowgirl energy with a beachy twist. The woven straw design keeps it light and breathable, while the turquoise beaded trim adds that standout, free-spirited vibe. It’s the kind of piece that instantly makes the outfit. Fit & FeaturesCurved wide brim, Colored beaded trim, Vintage-inspired look, 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 Sun Chaser Straw Cowboy Hat in Natural
This "Misbehavin’" cap brings a playful attitude with bold embroidered lettering and a camouflage brim that gives it that cool country rebel vibe. Pair with your favorite looks for any plans. Fit & Features"Misbehavin'" embroidered script, Camouflage print brim, Baseball cap silhouette, Adjustable snap back 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 Misbehavin’ Camouflage Baseball Cap in Olive