Button Shorts
Button shorts are the ultimate must-have for every Windsor girl's wardrobe, bringing that effortless blend of chic and cheeky to any ensemble. Whether you're strutting your stuff down the boardwalk or hitting up a rooftop brunch with your besties, these shorts have got you covered in style. With their versatile flair, button shorts are perfect for showing off those legs and flaunting your fearless fashion sense. So go ahead, embrace the sunshine and let your outfit do the talking—because with button shorts, you're always ready to make a statement!
$29.90
A sleek pair of black faux leather high-rise shorts with side pockets and a cheeky hem.
$39.90
A pair of brown cow print denim shorts featuring a mid-rise waist and classic five-pocket design.
$32.90
A pair of grey acid wash high-rise denim shorts with distressed details and a frayed hem.
$36.90
A pair of mid-rise, relaxed-fit bermuda shorts in bold cheetah-print non-stretch denim.
$32.90
A pair of dark denim mid-rise shorts with a frayed hem and vintage-inspired fabric.
$36.90
A pair of light denim mid-rise shorts featuring unique seam detailing and a form-hugging fit.
$34.90
A pair of medium wash, high-rise denim shorts featuring a frayed hem and five-button fly closure.
$39.90
A sleek pair of black faux leather hot shorts with a mid-rise waist and cheeky hem.
$32.90
A trendy pair of grey mid-rise denim shorts featuring an acid wash design and form-hugging fit.
$13.97 $32.90 58% off
A pair of dark denim mid-rise shorts featuring button-trimmed front pockets and a form-hugging fit.
$32.90
A pair of light denim mid-rise shorts featuring a raw frayed hem and classic five-pocket design.
$34.90
A pair of medium wash high-rise denim shorts featuring distressed accents and a frayed hem.
$32.90
A pair of medium wash, mid-rise denim shorts featuring a form-hugging fit and trendy cutoff hem.
$13.97 $34.90 60% off
A pair of grey high-rise denim shorts featuring a frayed hem and five-button front closure.
$39.90
A pair of medium denim high-rise shorts featuring dramatic side fringe and classic five-pocket styling.
$32.90
A pair of fitted khaki denim shorts featuring a mid-rise waist and front and back pockets.
$36.90
A medium wash denim skort featuring a mid-rise waist, button-up front, and mini-length hem.
$32.90
A pair of dark denim high-rise shorts with a form-hugging fit and four-pocket styling.
$32.90
A pair of light denim high-rise shorts featuring a frayed hem, five pockets, and classic fit.
$34.90
A black acid-wash denim skort with a mid-rise waist and hidden fitted shorts for coverage.
$34.90
A trendy dark denim mini skort with a mid-rise waist and bodycon fit, featuring a skirt overlay.
$39.90
A khaki denim skort with a high-rise waist and ruched drawstring for a unique, cute look.
$39.90
A trendy grey acid wash denim skort with a high-rise waist and adjustable side drawstring.
$34.90
An edgy brown denim skort with an acid wash, mid-rise waist, and mini-length hem.
$9.97 $32.90 70% off
A stylish olive twill skort with a ruched side seam and adjustable drawstring for a custom fit.
$29.90
A high-rise black faux leather skort with a bodycon wrap silhouette and mini-length hem.
$34.90
A yellow woven mini skort featuring a high-rise waist, side button accents, and a flirty ruffled hem.
$34.90
A high-rise grey acid wash denim skort with an envelope front and form-hugging mini-length hem.
$39.90
A vintage-inspired acid wash denim skort with a ruched side tie and built-in shorts for comfort.
$16.97 $39.90 57% off
A stylish medium denim skort featuring a pleated mini skirt overlay and edgy exposed pockets.
$29.90
A pair of chartreuse cotton shorts featuring a high-rise elastic waist, dual front pockets, and fitted silhouette.
Now Trending
Windsor Sealed With Charm Short A-Line Dress in White-2
$9.97 $38.90
74% off
Seal your look with this charming A-line dress for a rehearsal dinner or sunset dinner date! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, a padded bust, and a flattering short-length hem. Complete the look in chic block heels. Fit & FeaturesSleeveless sweetheart neckline, Adjustable spaghetti straps, Padded bust, A-line silhouette, Short-length hem, Poplin fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sealed With Charm Short A-Line Dress in White-2 | Size: L | Knit Fabric
Oh-so-contemporary and sleek, these smooth faux leather shorts feature a high-rise waist, front snap-button, hidden zipper closure, side pockets, seam detailing, and a fitted cheeky hem. The lined faux leather fabric has minimal stretch. Complete the look in a basic tee and boots for an edgy vibe. Fit & FeaturesHigh-rise waist, Front snap-button and hidden zipper closure, Side pockets, Seam detailing, Fitted, cheeky hem, Faux leather lined fabric, minimal stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Moves PU High-Rise Shorts in Black | Size: S | Leather
Create your own fairytale this Halloween with hot shorts that feature a chic tiered lace design and a cheeky fit. Perfect for creating a masquerade-inspired costume or classic icons. Complete costume with the matching mask or plaid top. Fit & FeaturesStretchy knit fabric with tiered floral mesh design, Mid-rise elasticized waist, Cheeky bottom coverage, Form-hugging fit, Shorts in size small have an 8.5" front rise with a 2" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fairytale Tiered Lace Hot Shorts in Pink | Size: M | Knit Fabric/Mesh Fabric
Take the stage in this rhinestone hot shorts and heat the scene! Fit & FeaturesRhinestone embellishments, Stretchy cotton-blend knit fabric, Low-rise waist, Fitted silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Center Stage Rhinestone Hot Shorts in Black-2 | Size: S | Cotton/Knit Fabric/Rhinestone
Such A Sweetheart Corset Lace-Up A-Line Short Dress in Light Blue
$9.97 $48.90
80% off
Capture sweet vibes in this flirty corset short dress designed with a striking lace-up back design, a corset-style bodice that snatches your waist, and a flattering A-line silhouette. Pair with bow earrings. Fit & FeaturesPoplin woven fabric, woven lining, Sweetheart neckline with adjustable drawstring tie, Adjustable spaghetti straps, lace-up back design, Underwire bust, corset-bodice, flexible boning, Side zipper and hook-eye closure, A-line short silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Such A Sweetheart Corset Lace-Up A-Line Short Dress in Light Blue | Size: L | Woven Fabric
Elevate your style with these hot shorts for any fun plans! These mid-rise shorts provide a comfortable fit and accentuate your curves in a sleek, form-hugging fit. Fit & FeaturesWoven fabric, Mid-Rise waist, Back zipper closure, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor One And Only Mid-Rise Hot Shorts in Black | Size: M | Woven Fabric
Shake it up in this leopard ruffle hot short for a night on the prowl! Fit & FeaturesLeopard print, mesh fabric, stretchy knit lining, High-rise waist, Ruffled silhouette, Form-hugging fit, Runs true to size, Shop The Matching Top: She's A Wild One Leopard Ruffle Tube Top Free Shipping on All Orders Over $75. | Windsor She's A Wild One Leopard Ruffle Hot Shorts | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
Bring the fierceness to the night in these leopard shorts made for dancing all concerts or the bar! With a flattering high-rise waist and ruffled hem, these shorts are perfect for stepping up your style. Fit & FeaturesLeopard print, stretchy knit fabric, High-rise waist, Ruffled short hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Maybe Tonight Leopard Ruffle Shorts | Size: L | Knit Fabric
Set the tone in this spicy ruffled hot short with a flattering low-rise waist that flaunts your figure! Pair with the matching top to complete the vibe. Fit & FeaturesMesh-lined fabric, Low-rise waist, Ruffled, fitted silhouette, Runs true to size, Shop The Matching Top: Summer Spice Lace-Up Ruffle Crop Top Free Shipping on All Orders Over $75. | Windsor Summer Spice Low-Rise Ruffle Hot Shorts in Pink | Size: L
Turn up the heat in these ponte micro shorts this season! Featuring a high-rise waist for a flattering fit, a form-hugging silhouette to accentuate your curves, and a cheeky cut to show off those legs. Complete the look in a graphic tee and sneakers! Fit & FeaturesPonte fabric, minimal stretch, High rise waist, Form-hugging fit, Cheeky cut micro hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Make It Hot High Rise Ponte Micro Shorts in Black | Size: M
Button Shorts
Buttoned shorts are basically your secret weapon for turning any day into a main character moment. There’s just something about those crisp, tailored details that say, “Yes, I planned this look, and yes, I nailed it.” Whether you’re running errands, hitting brunch with your crew, or plotting that spontaneous road trip, these shorts are the ultimate partner in crime. They walk the line between polished and playful, giving you the power to dress up or down without missing a beat. The best part? Buttoned shorts come in all the vibes—from high-waisted silhouettes that give you legs for days to relaxed fits that practically beg for a twirl on the dance floor. You can play with fabrics too, like breezy linens that keep you cool or structured denim that brings all the attitude. And don’t even get us started on the color game—think classic neutrals for easy pairing, or bold hues when you want to make a statement. If you’re eyeing a pair as a gift, just know you’re about to become someone’s favorite person. Buttoned shorts are a go-to for birthdays, bestie swaps, or that just-because surprise that says, “I get your style, and I love it.”
When it comes to styling, buttoned shorts are like your wardrobe’s BFF—they just get along with everyone. Tuck in a fitted tank for that effortless “I woke up like this” energy, or throw on a flowy blouse and some chunky jewelry for instant glam. If you’re feeling a little extra, layer with an oversized blazer and lace-up sandals for a look that’s equal parts boss and babe. They’re made for spontaneous adventures: picture yourself grabbing iced coffee, window shopping, and snapping pics with your squad, all while serving up major style. And let’s not forget the practical perks—those button details aren’t just for show; they add structure and keep everything in place, so you can move, groove, and live your best life without a single wardrobe malfunction. If you’re new to buttoned shorts, start with a classic cut in a neutral shade for max versatility, then branch out into playful patterns or unexpected textures as your confidence grows. For those who already live in shorts, these are the upgrade your closet’s been waiting for—think of them as your ticket to effortless cool, no matter where the day takes you.
Shopping for buttoned shorts is all about finding that perfect combo of fit, fabric, and flair. Pay attention to the rise—high-waisted styles are super flattering and pair well with crop tops, while mid-rise options give off a laid-back, retro vibe. If you’re gifting, consider the recipient’s style; go for classic cuts if they love timeless pieces, or pick something with standout buttons and bold details for your trendsetting friend. And if you’re just here to treat yourself (as you should), don’t be afraid to try something new—maybe a paperbag waist for extra drama, or a utility-inspired look for a little edge. No matter your pick, buttoned shorts are the kind of staple that makes every outfit feel intentional and every day a little more fun. Ready to explore more styles? Check out our full lineup of Cute Shorts and find your next obsession.