High Waist Pajama Shorts
Dreaming of those cozy nights and lazy mornings? High waist pajama shorts are here to make your slumber style as chic as your daytime wardrobe. Picture this: a perfect blend of comfort and cuteness that hugs you in all the right places. Whether you're lounging around the house, having a Netflix marathon, or catching up on beauty sleep, these shorts are your go-to for feeling fabulous even when you're just chilling. Slip into something more comfortable and let those good vibes roll all night long!
$29.90
A pair of high-rise leopard print shorts featuring a ruffled hem for a bold, playful look.
$34.90
A sassy leopard print short with high-rise waist and all-over sequin embroidery for glam nights.
$19.90
A pair of black ponte micro shorts with a high-rise waist and form-hugging silhouette.
$29.90
A leopard print ruffle short with a high-rise waist and form-hugging fit.
$14.97 $36.90 59% off
A pair of multi-color watercolor print woven shorts featuring a high-rise waist and relaxed fit.
$16.97 $39.90 57% off
A chic pair of ivory eyelet lace shorts featuring a high-rise waist and dual front pockets.
$19.90
A charming pair of white knit pajama shorts featuring a cherry print and ruffled hem.
$9.97 $19.90 50% off
A pair of light blue rib knit pajama shorts featuring a playful popsicle print and ruched side seams.
$29.90
A pair of chartreuse cotton shorts featuring a high-rise elastic waist, dual front pockets, and fitted silhouette.
$24.90
A sleek beige scuba nylon shaper short offering firm compression and an ultra high-rise waist.
$26.90
A pair of off-white woven shorts featuring a smocked high-rise waistband and ruffled tier design.
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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
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: L
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
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
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
Create an iconic 'fit for concerts and festivals with these curve-hugging hot shorts featuring a low-rise waist, front studded trim, and cheeky fit. Fit & FeaturesWoven fabric, moderate stretch, Low-rise elasticized waist, Front-studded trim, Cheeky form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Iconic 'Fit Studded Hot Shorts in Burgundy | Size: L | Woven Fabric
High Waist Pajama Shorts
When it comes to leveling up your chill game, nothing hits quite like high waisted pajama shorts. These are more than just sleepwear—they’re a whole mood, ready to take you from midnight snacking in the kitchen to lazy brunches on the couch with your besties. The magic of high waist pajama shorts is all in the details: think buttery-soft fabrics that feel like a hug, waistbands that never dig, and just the right amount of coverage to keep you comfy without sacrificing style. Whether you’re a lounge queen who lives for cozy movie marathons or you need something breezy for those late-night FaceTime catch-ups, these shorts are your ticket to feeling cute and totally at ease. And if you’re shopping for your ride-or-die bestie, your sister, or even your mom, trust—these make the kind of gift that says, “I get you, and I want you to live your best lounge life.” There’s something about slipping on a pair of pajama jean shorts or high waisted pajama shorts that instantly boosts your confidence, like you’re ready to take on the world (or at least your next group chat selfie).
Let’s get real: finding your perfect pair is all about knowing what makes you feel unstoppable. If you love a snug fit that still lets you move, look for styles with a good amount of stretch and a wide, elastic waistband—no one wants to be adjusting their shorts all night. For the ultimate in laid-back vibes, go for super-soft knits or playful prints that match your personality, because your sleepwear should be as fun as you are. And let’s not forget: high waisted pajama shorts are basically made for mixing and matching, so you can pair them with your fave oversized tee, a silky cami, or even that hoodie you “borrowed” from your last situationship. They’re also a total lifesaver for travel—lightweight, easy to pack, and cute enough to wear from the hotel room to the lobby coffee run. If you’re the type who loves a good sleepover or just wants to treat yourself to a little extra comfort, these shorts are a must-have addition to your loungewear lineup. And for those who want even more options, don’t miss out on the full lineup of Elastic Waist Sleep Shorts for endless ways to keep your downtime looking and feeling luxe.
At the end of the day, high waisted pajama shorts are all about giving you that confident, carefree energy—whether you’re winding down after a long day or turning a lazy morning into an excuse to celebrate yourself. They’re the kind of staple you’ll reach for again and again, perfect for gifting to the girls who deserve a little extra love or for treating yourself to a slice of everyday luxury. Keep your look effortless, your comfort on lock, and your vibes high—because you deserve to feel amazing, even when you’re just hanging out at home.