Top Windsor Deals for September 2025

Shine bright in our Windsor Rhinestone Embellished High Waist Denim Shorts. These black denim shorts feature a high waist for a flattering fit, complete with belt loops and three functional pockets including a zipper closure. The frayed hem adds a casual vibe, while rhinestone embellishments scattered across the front provide glamorous detail. Made from faded black denim, they offer comfort and style for any casual occasion. Pair them with a simple top to let the shorts stand out. Take advantage of Windsor's free shipping on orders over $75.

Let's talk about these light brown suspender shorts for a sec! You'll be ready for the desert in a flattering high rise fit, a standard five pocket and belt loop design, and hanging suspender traps with large silver studs connected to half pant legs with O ring zippers. Shorts offer a slim fit and are composed of a smooth cargo knit fabric with minimal stretch. Model is 5'9 with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Studded Suspender Shorts Pant in Light Brown | Size: S | Knit Fabric

These rolled hem jean shorts will be your new go-to denim! They feature a high rise waist, the traditional five pocket and belt loop design, a front button down closure, distressed detailing, and a rolled and frayed hem. The medium wash jean shorts are composed of a denim fabric with no stretch. Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor High Rise Rolled Hem Jean Shorts in Denim | Size: S

These shorts are diva-approved for your trendsetting looks! They feature a mid-rise fit, a single button with zipper closure, a five pocket with belt loop design, moderate distressed detailing throughout and a fab bermuda length. Shorts are composed of a denim fabric that offers a relaxed fit with a moderate stretch. Free Shipping on All Orders Over $75. | Windsor Distressed Diva Bermuda Shorts in Black | Size: S

Make sure your look is stylishly frayed in these high rise jean shorts! They feature the traditional five pocket and belt loop design, a front button and hidden zipper closure, slight distressed detailing, a dark tuxedo stripe down each side, and a frayed hem. The light wash short are composed of a denim fabric with moderate stretch. Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Fray It With Style Jean Shorts in Denim | Size: XS

Live it up and live your best style in these snake print shorts! They feature a high rise paperbag waist, a tie front belt, slanted front pockets, a side zipper closure, and flowy shorts. The bottoms are composed of a woven fabric with no stretch and feature an eye-catching black and gray snake print. Free Shipping on All Orders Over $75. | Windsor Live It Up Snake Print Shorts | Size: XS | Woven Fabric

Ready, set, go! You're all set to go in these light blue paperbag shorts! They feature a high rise waist, a tie front waist and wide leg opening. The all over white stripes create a fresh contrast for the dreamy light blue background. Shorts are composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Be sure to pick up the matching top to complete your look! Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small. 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 Set In Stripes Paperbag Shorts in Light Blue | Size: XS | Woven Fabric

Oasis by EuninaFreshen up your spring wardrobe with this pair of high waist destructed shorts! The white denim bottoms feature a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, distressed detailing down the front, and a cuffed hem. The shorts offer moderate stretch and a form-fitting style. Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor High Waist Destructed Shorts in White | Size: XS

Fun times in these black shorts guaranteed! They are made from a faux suede fabric and feature a high waist, an elastic waist band, a cheeky fit, and lots of fab fringe throughout. Model is 5'8 with a 32" bust, 24.5" waist and 36" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Fun Times Fringe Shorts in Black | Size: S | Faux Suede

Say what? You love these blue jean shorts? So do we! They feature a high waist, the traditional five pocket and belt loop design, a single button and zipper closure, and frayed hems. Jeans are composed of a denim fabric that offers a form hugging fit with a moderate stretch. Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Fray What Denim Shorts | Size: XS

These stylishly destructed jean shorts are a must have for sure! They feature a mid rise waist, the traditional five pocket and belt loop design, a single front button and zipper closure, and major distressing down the front with a frayed hem. The bermuda shorts are composed of a medium wash denim fabric that offers moderate stretch. Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Stylishly Destructed Jean Shorts in Denim | Size: S

Keep your look wild and free with these casual cute leopard print shorts! They feature a high rise elastic banded waist, a front drawstring, and relaxed fitting shorts. Bottoms are composed of a soft knit fabric with moderate stretch. Don't forget the matching top for the purrfect look! Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Wild And Free Shorts in Leopard | Size: S | Knit Fabric

Lace up your look with these black ponte shorts! They feature a high rise waist, a back zipper closure, a lattice lace up front detail, and a short, form hugging fit. The shorts are composed of a ponte knit fabric with moderate stretch. Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Lace Up Ponte Shorts in Black | Size: XS | Knit Fabric

Spend a gorgeous summer day outdoors in these red gingham paper bag shorts! They feature a high paper bag waist with a tie belt, slanted front pockets, a hidden back zipper and hook and eye closure, and a relaxed fit throughout. Shorts are composed of a woven fabric with an all over gingham print. Pair with matching crop top to complete the set! Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Picnic Time Gingham Paper Bag Shorts in Red | Size: XS | Woven Fabric

Keep it poised in trendy paperbag shorts. The high waist shorts feature an elastic paperbag waist, a cinching tie waist belt, slant hand pockets, and subtle pleated details. The relaxed fit waist leads to a wide leg opening. The shorts are composed of a woven fabric that offers little to no stretch. Complete your look with a puff sleeve blouse and strappy open toe heels for a sophisticated outfit. Fits & FeatureHigh rise fit, Elastic paperbag waist, Tie front belt, Slant hand pockets, Single faux back pocket, Pleated details, Woven fabric, no stretch, Black Shorts: Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.Pink Shorts: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small. Mauve Shorts: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small. Taupe Shorts: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small. 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 Poised Paperbag High Waist Woven Shorts in Black | Size: XS | Woven Fabric

Shake things up and create a stylish look with these snake print shorts! They feature a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, and a short, fitted look. The shorts are composed of a twill fabric that offers moderate stretch. Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size three. Free Shipping on All Orders Over $75. | Windsor Snake Things Up Twill Shorts | Size: 1

Showcase your stylish side with these plaid boucle shorts! They feature a high rise waist, a hidden side zipper and hook and eye closure, and front slanted pockets. The shorts are composed of a boucle woven fabric that offers no stretch and showcases a black hued plaid print. Don't forget to purchase the matching crop top! Sizes run small. Fit model recommends purchasing one size up. Free Shipping on All Orders Over $75. | Windsor Plaid Boucle Shorts in Black | Size: S | Woven Fabric

Be a total babe in these chic and trendy bandage biker shorts! They feature a high rise waist, a hidden back zipper and hook and eye closure, and fitted, form-hugging shorts. The bottoms are composed of a black bandage knit fabric that offers plenty of stretch. Free Shipping on All Orders Over $75. | Windsor Bandage Biker Shorts in Black | Size: XS | Knit Fabric

Add some fierceness to your 'fit with these trendy and fun jean shorts! They feature a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, and a frayed hem. The light wash jean shorts are composed of a denim fabric with moderate stretch and showcase a faint all over leopard print. Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor Leopard Print Jean Shorts in Denim | Size: XS

Oasis by EuninaElevate your denim game with these stylish shorts! They feature a high rise waist, a traditional five pocket and belt loop design, a single front button with zipper closure, light distressed detailing and a cuffed hem. Shorts are composed of a light medium wash denim fabric that offers a relaxed fit that offers a slight stretch. Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small. Free Shipping on All Orders Over $75. | Windsor On The Rise Cuffed Shorts in Denim | Size: XS

Level up in this hot piece! The shorts have a drawstring waist paired with basic slant pockets and a dolphin hem. The garment is composed of a sheen, metallic fabric that includes a nylon lining. Free Shipping on All Orders Over $75. | Windsor Level Up Metallic Shorts in Silver | Size: S | Nylon