Comfy Shorts
Comfy shorts are your ticket to laid-back days and spontaneous adventures—because who says you can’t look cute while keeping it chill? Whether you’re lounging with your crew, hitting up your favorite coffee spot, or just vibing at home, these shorts have your back. Slip into effortless style that feels as good as it looks, and let comfy shorts be the go-to pick for every plan.
$22.90
A pair of pink low-rise ribbed knit pajama shorts offering a cheeky, fitted silhouette.
$22.90
A comfy pair of ivory knit pajama shorts with a flattering mid-rise folded waist and cheeky bottom.
$26.90
A pair of off-white woven shorts featuring a smocked high-rise waistband and ruffled tier design.
$16.90
A pair of multi-color ribbed knit pajama shorts featuring a playful gummy bear print and cheeky fit.
$14.90
A pair of beige high-rise pajama shorts featuring bunny graphics and a stretchy, soft knit fabric.
$29.90
An airy pair of light blue cotton shorts featuring a smocked drawstring waist and playful ruffled hem.
$17.90
A pair of pink knit pajama shorts featuring a playful dice print, elastic waist, and side slits.
$32.90
A pair of high-rise dark denim shorts with a form-hugging fit and stretch fabric.
$32.90
A pair of white mid-rise denim shorts with distressed accents and a form-hugging fit.
$34.90
A pair of olive mid-rise denim shorts with a trendy lace-up side design for festival flair.
$34.90
A pair of ivory knit shorts with a cheeky fit and tiered ruffled design for festivals.
$29.90
A pair of black rhinestone-embellished hot shorts in stretchy cotton-blend knit fabric.
$24.90
A pair of black woven mid-rise shorts featuring a sleek, form-hugging fit for stylish comfort.
$36.90
A pair of black knit shorts with square-shaped rhinestone accents and a cheeky, low-rise fit.
$29.90
A chic pair of red gingham ruffle shorts with a low-rise waist and cheeky bottom.
$12.97 $30.90 58% off
A trendy pair of camel faux suede shorts featuring a stylish lace-up front and back zipper closure.
$24.90
A pair of snake print, low-rise knit shorts with a form-hugging, cheeky fit for festivals.
$32.90
A trendy pair of grey mid-rise denim shorts featuring an acid wash design and form-hugging fit.
$32.90
A pair of light denim high-rise shorts with trendy distressed accents and a frayed cut-off hem.
$29.90
A playful pair of pink low-rise shorts featuring ruffled mesh-lined fabric and a fitted silhouette.
$24.90
A stylish pair of black and white gingham shorts with a mid-rise waist and ruffled hem.
$16.90
A pair of white cherry print pajama shorts in soft, stretchy rib knit fabric for cozy lounging.
$26.90
A pair of black gauze shorts featuring a high-rise smocked waist and tiered ruffled design.
$26.90
A taupe knit short with a high-rise waist and trendy scalloped hem for a boho vibe.
$32.90
A pair of high-rise dark denim shorts featuring distressed details and a relaxed fit in cotton.
$32.90
A pair of dark denim high-rise shorts with a form-hugging fit and four-pocket styling.
$16.90
A cheeky, form-hugging pajama short in white with a playful lemon print and stretchy knit fabric.
$36.90
A pair of mid-rise denim hot shorts with a color wash tint and cheeky fit.
$36.90
A chic pair of natural linen-blend shorts featuring a belted waist and dual front pockets.
$19.90
A charming pair of white knit pajama shorts featuring a cherry print and ruffled hem.
$24.90
A flirty pair of white eyelet ruffle swim shorts with a high-rise elasticized waist.
$16.90
A playful pair of pink knit pajama shorts featuring a zesty orange print and cheeky fit.
$12.90
A pair of red polka dot knit pajama shorts with dainty lace trim and a mini bow detail.
$32.90
A pair of medium wash, mid-rise denim shorts featuring a form-hugging fit and trendy cutoff hem.
$32.90
A pair of grey acid wash high-rise denim shorts with distressed details and a frayed hem.
$34.90
An ivory chiffon eyelet short featuring a smocked mid-rise waist, ruffled silhouette, and lace trim.
$34.90
A pair of medium wash, high-rise denim shorts featuring a frayed hem and five-button fly closure.
$36.90
A pair of mid-rise, relaxed-fit bermuda shorts in bold cheetah-print non-stretch denim.
$16.90
A pair of off-white ribbed knit pajama shorts featuring a playful horse print and cheeky, form-hugging fit.
$36.90
A pair of light denim mid-rise shorts featuring unique seam detailing and a form-hugging fit.
$29.90
A pair of yellow sheer lace hot shorts featuring tiered ruffles and a cheeky, form-hugging fit.
$29.90
A pair of medium wash, mid-rise denim shorts with a form-hugging fit and cheeky bottom.
$36.90
A flattering pair of medium denim high-rise shorts with a stylish cross-over hem and slight stretch.
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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: L | 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 Ivory | Size: S | Knit Fabric/Mesh Fabric
Short, sweet, and exceptionally poised! These high-rise denim shorts are everything for elevating your style. Pair with the matching vest. Shop Matching Vest: Exceptional Poise Sleeveless Button Denim VestFit & FeaturesDark wash denim fabric with stretch, High-rise waist, Front button and hidden zipper closure, Form-hugging fit, Short-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Exceptional Poise High Rise Denim Shorts in Dark Denim | Size: S
Style up your Halloween costumes with these sleek faux leather hot shorts featuring a mid-rise waist and a cheeky form-hugging fit. Dress up as a champion racer with the checkered bustier and cropped jacket, or as a sporty babe with the jersey tee and football rhinestone clutch. Fit & FeaturesStretchy faux leather fabric, Mid-rise elasticized waist, Cheeky form-hugging fit, Shorts in size small have a 9" front rise with a 1.5" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sleek Vibe Faux Leather Hot Shorts in Black | Size: L | Leather/Rhinestone
Turn up the shine in these groovy metallic faux leather shorts perfect for themed parties! With a high-rise waist and form-hugging fit, these shorts accentuate your curves while providing a flattering silhouette. The cargo flap pockets offer functionality while the front button and hidden zipper closure secure the style. Complete the look in a mesh long sleeve top and heels! Fit & FeaturesCoated metallic faux leather fabric, slight stretch, High-rise waist, Form-hugging fit, Front button and hidden zipper closure, Three waist pockets, lower cargo flap pockets, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Turn Up Cargo Metallic Faux Leather Shorts in Black | Size: L
Put on a show arriving in these rhinestone denim shorts! They feature a flattering high-rise waist, and stunning rhinestone swag chains across the front for a touch of glamour. The distressed accents add a trendy edge, while the fitted hem ensures a perfect fit. Complete the look in a bodysuit and boots for a concert or music festival! Fit & FeaturesHigh-rise waist, Rhinestone swag chains across the front, Distressed accents, fitted hem, Front button and hidden zipper closure, Five-pocket styling, belt loop accents, Medium wash denim fabric, no stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pop Star Rhinestone High-Rise Denim Shorts in Med Denim | Size: L
Grab your besties and make plans to rock these mid-rise denim shorts for fun under the sun! The mid-rise waist and form-hugging fit flatter your curves, while the distressed accents and cut-off hem add a touch of edge. Complete the look in a cute bodysuit and platform sneakers! Fit & FeaturesDenim fabric, minimal stretch, Mid-rise waist, Distressed accents, cut-off hem, Form-hugging, Front button and hidden zipper closure, five-pockets, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunny State Mid-Rise Distressed Denim Shorts in White | Size: S
Create a sassy and chic night out look with these hot shorts designed with leopard-printed faux suede fabric. They feature a high-rise waist and a cheeky form-hugging fit. Style with a crop top and boots! Fit & FeaturesLeopard printed faux suede fabric, High-rise waist, Cheeky form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sassy Chic Leopard Print Faux Suede Hot Shorts in Brown | Size: M
Create a sassy look for your next night out in these leopard print hot shorts featuring a high-rise waist and a cheeky form-hugging fit. The all-over sequin embroidery adds a cool glam vibe to the sultry style. Fit & FeaturesLeopard print woven fabric with knit lining, plenty of stretch, All-over clear sequin embroidery, High-rise waist, Side zipper with hook-eye closure, Cheeky form-hugging fit, Shorts in size small have an 11" front rise with a 1" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sassy Look Sequin Leopard Print Hot Shorts | Size: S | Knit Fabric/Woven Fabric
Windsor Time To Celebrate Sequin Hot Shorts in Silver
$15.97 $36.90
57% off
Flaunt your sparkle in these sequin hot shorts! With a cheeky fit and mid-rise elastic waist, these shorts bring the party vibes. Perfect for dancing the night away! Fit & FeaturesSequin embellished sheer knit fabric, knit lining, moderate stretch, Mid-rise elasticized waist, Cheeky fit bottom, Shorts in size small have a 10" front rise with a 1.5" inseam, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Time To Celebrate Sequin Hot Shorts in Silver | Size: L | Knit Fabric
Comfy Shorts
When it comes to leveling up your loungewear game, nothing hits quite like a pair of comfy shorts. These aren’t your average gym class relics—think soft, stretchy waistbands, dreamy fabrics that feel like a hug, and silhouettes that move with you whether you’re curled up with your favorite romcom or turning your living room into a dance floor. Comfy shorts are the ultimate go-to for lazy mornings, spontaneous road trips, or running errands when you still want to look cute without sacrificing comfort. They’re the piece you reach for when you want to feel totally at ease, but still put-together enough to answer the door for your bestie (or that surprise food delivery). The best part? They come in so many styles—flowy, fitted, high-waisted, ribbed, or cottony soft—so you can match your mood, your plans, or just your vibe for the day. Whether you’re all about that “woke up like this” energy or you love to accessorize your lounge look with fuzzy socks and an oversized crewneck, there’s a pair of comfy shorts ready to be your partner in crime.
Comfy shorts aren’t just for you—they make an epic gift for your squad, too. Imagine wrapping up a pair for your best friend who’s always crashing at your place, or slipping them into a care package for your sister who just moved into her first apartment. They’re the kind of present that says, “I see you, I love you, and I want you to chill in style.” And don’t even get us started on the endless ways to wear them: pair with a crop top for a TikTok-worthy look, layer with a slouchy sweater for movie marathons, or mix and match with your favorite bralette for a sleepover that turns into an all-day hang. For those days when you want to keep things breezy but still look totally on point, comfy shorts are a must-have. And if you’re all about that laid-back lifestyle, don’t forget to check out our Comfy Dresses for even more ways to keep it cute and cozy.
Let’s be real—life’s too short to wear anything that doesn’t make you feel like your best self, and comfy shorts are here to remind you that comfort and confidence go hand in hand. Whether you’re treating yourself or spoiling someone special, these shorts are the foundation of every off-duty wardrobe. Slip into that cloud-soft fabric, kick back, and let the good vibes roll. With endless options for styling and gifting, comfy shorts are the secret weapon every Windsor girl needs in her closet—ready to take on whatever the day (or night) brings, one carefree moment at a time.