Stylish Baseball Caps

Stylish baseball caps are the ultimate finishing touch for any look—whether you’re running late to brunch or just want to keep your vibe effortlessly cool. Throw one on and instantly level up your outfit with a dash of attitude and a sprinkle of mystery (because who doesn’t love a little intrigue?). From casual hangs to spontaneous adventures, these caps are your go-to accessory for looking cute, feeling confident, and keeping the good times rolling.

Show Filters

Sort: Recommended

Size

Color

Price

All Filters

27 results

Sort

Windsor Sorry I'm Late, I Stopped For Coffee Baseball Cap in Brown

$12.90

A brown baseball cap with an embroidered coffee-themed script and adjustable strap for a perfect fit.

Cowboys Club Two-Tone Baseball Cap in Brown

$18.90

A structured cotton baseball cap in brown with a two-tone design and "Cowboys Club" embroidered patch.

Hotter Than Ever Leopard Baseball Cap

$16.90

A structured cotton baseball cap featuring a bold leopard print brim and "Hotter Than Ever" embroidery.

Now Trending

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 Cold Girl Classic Faux Fur Bucket Hat in Black

$22.90

(1)

Fuzzy, fabulous, and unapologetically extra. This faux fur bucket hat brings that cozy-luxe vibe to any outfit—perfect for layering up, heading out, or just serving “don’t mess with my winter aesthetic” energy. Fit & FeaturesPlush faux fur exterior, Adjustable inner strings for a snug fit, Classic bucket hat silhouette, 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 Bucket Hat in Black

Off Duty Faux Leather Cabby Hat in Black

$18.90

(1)

Serving effortless cool with zero effort—this faux leather cabby hat pulls your whole look together in seconds. Perfect for when you want that model-off-duty vibe without even trying. Fit & FeaturesFaux leather material, Round top, seam accents, button detail, Short curved brim, Woven lined interior, Interior adjustable strings, How To Style For Spooky Season:Pair with a sleek bodysuit and skirt for a fab DIY Halloween look! 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 Off Duty Faux Leather Cabby Hat in Black

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

Windsor Low Key Cool LA Baseball Cap in White

$15.90

(1)

Repping the city never looked this effortless. This LA embroidered baseball cap is the laid-back staple you’ll throw on with everything from streetwear fits to off-duty looks. Fit & FeaturesClassic baseball cap silhouette, Structured curved brim, LA embroidered detail on front, Adjustable back strap for a custom 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 Low Key Cool LA Baseball Cap in White

Sale

Windsor Autumn Stroll Corduroy Baseball Cap in Brown

$6.97 $14.90
53% off

(1)

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 Brown

Windsor Cold Girl Classic Faux Fur Hat in Beige

$25.90

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

Windsor Gloria Cap Sleeve Tie Back Mermaid Formal Dress in Navy Blue

$69.90

(1)

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: XS | Knit Fabric

Windsor Cool Girl Cozy Faux Fur Bucket Hat in White

$18.90

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

Cold Girl Era Faux Fur Trapper Hat in Ivory

$32.90

Snow-day vibes, but make it chic. This faux fur trapper hat brings warmth and attitude with a plush texture and cozy ear flaps that make bundling up actually feel like a style moment. Fit & FeaturesSoft faux fur exterior and lining, Trapper silhouette with ear flaps, Adjustable buckle 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 Cold Girl Era Faux Fur Trapper Hat in Ivory

Stylish Baseball Caps

When it comes to finishing off a look—whether you’re headed out for a brisk January walk, running errands, or just embracing a low-key vibe—a stylish baseball hat is the ultimate accessory. It’s the piece that pulls everything together without trying too hard, sliding seamlessly into your closet right alongside your favorite jeans and go-to sneakers. There’s something effortlessly cool about tossing on a baseball cap, especially when the weather is unpredictable and you want to keep your hair in check or add a little edge to your winter layers. Baseball hats aren’t just for summer or game day; they’re seasonless, endlessly versatile, and a clever way to inject personality into any outfit. From monochrome neutrals that play nice with your puffer jacket to pops of color that brighten up grey winter mornings, a well-chosen cap can be the difference between “just rolled out of bed” and “intentionally undone.”

If you’re shopping for yourself, think about what you want your hat to say—maybe you lean into classic shades for a timeless look, or maybe you gravitate toward unexpected textures and details, like a brown fur bucket hat for women who want to mix cozy and cool in equal measure. There’s a certain confidence in choosing a Windsor hat that feels both on-trend and uniquely you, whether you’re pairing it with a tailored coat for a quick coffee run or slipping it on with joggers for a spontaneous road trip. Don’t underestimate the gifting potential, either. Stylish baseball hats make thoughtful, practical gifts—think best friend birthdays, Galentine’s surprises, or a little pick-me-up for the sister who’s always stealing your accessories. They’re a fit for everyone: the friend who lives in athleisure, the cousin who’s impossible to shop for, or even your mom, who’s finally embracing the “off-duty model” look. And with options that adjust for the perfect fit, there’s no guesswork involved—just easy, wearable style that feels personal every time.

Of course, shopping for Windsor hats isn’t just about what looks good on the shelf; it’s about how it works for real life. Consider the details: adjustable closures for a custom fit, breathable fabrics for all-day comfort, and silhouettes that flatter every face shape. Maybe you’re after a cap that transitions effortlessly from gym to brunch, or you want something a little more luxe—like a brown fur bucket hat that brings a playful twist to winter layering. The beauty of the baseball cap is its ability to adapt: tuck it into your tote for a day out, toss it in your gym bag, or use it as a quick fix for second-day hair. If you’re looking for more inspiration or ready to expand your collection, discover the latest styles in our curated selection of Adjustable Baseball Caps for Women. However you wear it, a great hat isn’t just about covering up—it’s about standing out, owning your style, and making every day feel a little more put together.

Reset Your Password

Email Sent

Order Status

Stylish Baseball Caps

Home Stylish Baseball Caps

Now Trending

Stylish Baseball Caps

Related Collections