Cool Summer Outfits
Sunshine, beach days, and endless adventures are calling your name, and girl, it's time to answer with some seriously cool summer outfits! Whether you're hitting the boardwalk or brunching with your besties, we've got the styles that'll have you turning heads faster than a sunset on a hot July night. From flirty florals to breezy silhouettes, these looks are all about keeping it chic while you own every moment under the sun. So grab your shades and dive into a world where effortless style meets unforgettable summer vibes. Let's make this summer one for the books!
$49.90
An ivory floral skater dress with a corset bodice and flared hem, perfect for sunny occasions.
$38.90
A white ribbed knit midi dress featuring a V-neckline, spaghetti straps, and a high front slit.
$34.90
A black acid-wash denim skort with a mid-rise waist and hidden fitted shorts for coverage.
$46.90
A sultry brown maxi dress featuring a twist plunge V-neckline, cutout bodice, and ruffled slit.
$48.90
A flirty white mini skater dress featuring a breezy eyelet knit and charming tie-back detail.
$59.90
A light blue midi dress featuring a corset bodice, lace-up back, and sweetheart neckline.
$35.90
A natural-colored sleeveless wrap mini dress in stretchy knit fabric with a form-hugging fit.
$26.90
A rust satin paisley scarf top with a strapless neckline and tie-back design for effortless style.
$44.90
A yellow floral skater dress with a strappy tie-back and ruffled mini-length hem.
$32.90
A strapless yellow mini dress with ruched sides and a playful ruffled hem in knit fabric.
$44.90
A brown cotton-blend romper with a halter plunge neckline and playful skater silhouette.
$24.90
An airy orange woven crop top with a sweetheart neckline and charming tie-back bow design.
$42.90
A sultry strapless yellow mini dress with ruffled trim and a flattering bodycon silhouette.
$46.90
An ivory striped midi dress with cutouts, adjustable straps, and dual side slits for casual elegance.
$19.97 $32.90 39% off
A brown knit halter skater dress with ruched waist and flirty double-layered skirt.
$52.90
A white eyelet lace skater dress featuring a scoop neckline and ruffled mini-length hem.
$42.90
A medium denim halter romper with lace-up cutout bust and form-hugging fit for sunny days.
$22.97 $49.90 54% off
A white eyelet mini dress featuring a strapless folded neckline and flirty front slit.
$46.90
A charming floral babydoll mini dress in natural with a flowy ruffled silhouette and smocked bust.
$32.90
A pair of white mid-rise denim shorts with distressed accents and a form-hugging fit.
$24.97 $54.90 55% off
A floral ivory skater dress featuring a halter V-neckline and voluminous silhouette in poplin fabric.
$44.90
A yellow skater dress featuring eyelet lace embroidery and a stretchy smocked bodice.
$22.90
A white off-the-shoulder crop top with a sweetheart neckline and adjustable drawstring for summer fun.
$19.97 $35.90 44% off
A strapless taupe midi dress with a tropical print and flared hem, perfect for vacations.
$30.90
A breezy ivory linen-blend crop top with a collared V-neckline and twist-front hem.
$19.97 $44.90 56% off
A light blue strapless skater dress featuring eyelet cotton fabric and a flirty lace-up bust.
$56.90
A natural floral chiffon romper with a strapless neckline and flattering drop waist seam.
$42.90
A red gingham skater dress with lace trim and button details for a charming spring look.
$34.90
A high-rise grey denim skort with an edgy acid wash and envelope front skirt design.
$49.90
A black rib knit mini dress with a halter neckline and playful skater silhouette.
$21.97 $48.90 55% off
An off-white chiffon skater dress featuring a sheer corset bodice and cold-shoulder design.
$22.90
A pink woven crop top featuring ruffled straps, a square neckline, and a stretchy smocked bodice.
$54.90
A dazzling white bodysuit with rhinestone embellishments, padded cups, and a sheer mesh design.
$27.90
A chic ivory mini skort with a high-rise waist and dual front slits in ponte knit.
$22.90
A sleek black faux leather wrap skort with a high-rise waist and pleated detailing.
$34.90 - $42.90
A black crepe jumpsuit with a plunging V-neckline, midriff cutout, and halter neck design.
$36.90
A pink ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$34.90
A brown high-rise cargo mini skirt with vertical seams and side pockets in twill fabric.
$34.90
A dark denim cargo mini skirt with a removable belt and dual side pockets.
$49.90
A pair of black high-rise cargo denim jeans with a straight-leg silhouette and trendy flap pockets.
$19.90
A chic black sheer mesh bolero with blouson sleeves, perfect for layering over any outfit.
$38.90
A natural-colored lace A-line dress with a sleeveless square neckline and elegant short hem.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$42.90
A stylish pair of brown high-rise cargo pants with adjustable drawcord hems and multiple pockets.
$35.90
A pink sleeveless bodycon midi dress with stretchy knit fabric and a flattering square neckline.
$44.90
A casual denim shacket with a relaxed fit, button-up front, and convenient pockets.
$34.90
A trendy dark denim mini skort with a mid-rise waist and bodycon fit for versatile styling.
$34.90
An olive cotton-blend cargo mini skirt with a belted mid-rise waist and cargo pockets.
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Have a twirl-worthy moment in this gorgeous and glam satin skater dress. It features a sleeveless square neckline, adjustable spaghetti straps that lead to a cross-back and lace-up back design, a fitted bodice with a high waist, and a flirty skater silhouette. Style this dress with rhinestone earrings and new heels. Fit & FeaturesSleeveless, square neck, adjustable spaghetti straps, Built-in padded bust, Lace-up back design, Fitted bodice, high waist seam, Skater pleated silhouette, Satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor A Moment In Satin Skater Dress in Blue | Size: L | Rhinestone/Satin Fabric
Lustrous silk for your fancy needs. Show up to the celebration in this satin skater dress designed to fit and flatter every figure in a sleeveless cowl neckline, spaghetti straps, and a form-fitting bodice that leads to a short-length hem. Complete the look in fab block heels. Fit & FeaturesSleeveless cowl neckline, spaghetti straps, Form-fitting bodice, Skater style skirt, Short-length hem, Silky smooth satin fabric, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Silky Chic Satin Skater Dress in Blue | Size: M | Satin Fabric
A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels. Fit & FeaturesRibbed knit fabric with plenty of stretch, Off-the-shoulder neckline, fold-over accent, Long fitted sleeves, Short-length hem, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Staple Ribbed Knit Skater Dress in Pink | Size: XS | Knit Fabric
Flirt up the room at your next dressy affair in this adorable skater dress designed with a floral jacquard satin fabric for a chic look. It features a sleeveless sweetheart neckline with ruching at the bust and a tie-front detail, a corset bodice with vertical seam detailing, a lace-up back design to create that snatched fit, a V-shaped drop waist, and a short skater skirt with an iconic fit-and-flare silhouette. Fit & FeaturesFloral jacquard satin fabric with lace-trim lining, Sweetheart neckline, ruched underwire bust, tie-front detail, Thin adjustable shoulder straps, lace-up back, Corset bodice with vertical seam detailing, flexible boning, V-shaped drop waist, Short skater skirt, fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Flirt It Up Floral Jacquard Satin Corset Skater Dress in Ivory | Size: S | Satin Fabric
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag. Fit & FeaturesSleeveless V-neckline, Halter tie-back straps, open back, Stretchy smocked high waist, Short skater skirt, tiered ruffled design, Fit and flare silhouette, Twill fabric, woven lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunset Happy Hour Ruffled Skater Dress in Yellow | Size: M
Windsor Bling Fling Satin Rhinestone Skater Dress in Royal Blue
$20.97 $45.90
54% off
Show off a hint of bling in this satin skater dress for your next dressy soiree! Adorned with detachable rhinestone-embellished straps for a stunning sparkle, this dress will be the night's hit. The smooth satin-knit fabric offers plenty of stretch for comfortable wear. The short dress features a sleeveless square neckline, ruched side seams at the bodice, and a flattering fit-and-flare skater silhouette. Complete your look with rhinestone bow heels. Fit & FeaturesStretchy smooth satin-knit fabric, knit lining at the bust, Sleeveless square neckline, Detachable rhinestone-embellished thin straps, Side ruched seams at the bodice, High waist seam, Fit-and-flare skater silhouette, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Bling Fling Satin Rhinestone Skater Dress in Royal Blue | Size: L | Knit Fabric/Rhinestone/Satin Fabric
Create a sweet summer look that is oh-so-darling with this drop-waist skater dress. Designed with a lightweight woven fabric, the bodice is accented with a dainty lace trim for a pretty vibe. The short dress features a sleeveless sweetheart neckline, a ruched bust with a small tie-front adjustable detail, and thin tank straps leading to an alluring lace-up back for a customized fit. The asymmetric drop-waist is detailed with pleated side panels, flowing down to a tiered A-line silhouette for a flirtatious look. Style with hoop earrings and a charm necklace. Fit & FeaturesWoven fabric with lace trim woven lining, Sweetheart neckline, ruched bust, adjustable tie-front, Tank straps, lace-up back design, Back zipper and hook-eye closure, Asymmetric drop-waist, pleated side panels, Tiered A-line silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Darling Woven Drop-Waist Skater Dress in White | Size: XS | Woven Fabric
Be your own adorable muse in this sleeveless skater dress boasting a V-neckline and a ruffled skater silhouette. Complete the look with heels. Fit & FeaturesSheer lace fabric with knit lining, plenty of stretch, V-neckline with twist-front bust design, Adjustable spaghetti straps, V-shaped drop waist, Mini-length tiered ruffled skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Adorable Muse Ruffled Lace Skater Dress in White | Size: L | Lace Fabric/Knit Fabric/Sheer Lace Fabric
Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette. Fit & FeaturesEyelet knit fabric with knit lining, Sleeveless square neckline, underbust seam, Adjustable spaghetti straps, Skater silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sweet Look Eyelet Knit Skater Dress in White | Size: S | Knit Fabric
Spring forward in the cutest skater dress showcasing a head-turning strappy tie-back and a flattering ruffled mini-length hem that'll swoon everyone! Fit & FeaturesWoven fabric with woven lining, Square neckline with bust tie, Spaghetti straps, Strappy tie-back design, Skater silhouette, Ruffled mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Spring Forward Strappy Back Skater Dress in Yellow | Size: L | Woven Fabric
Cool Summer Outfits
When it comes to curating the ultimate collection of cool summer outfits, it’s all about dialing up the confidence and letting your style do the talking, no matter where the day (or night) takes you. Think of this as your personal backstage pass to an endless summer—where every fit is a mood, every detail is a vibe, and every look is a memory in the making. Whether you’re planning rooftop hangs with your crew, spontaneous road trips, or just living for those golden-hour selfies, the right outfit is your secret weapon. Lightweight fabrics, breezy silhouettes, and playful pops of color set the stage for your main character energy. You’ll want to keep an eye out for pieces that move with you, keep you cool, and let your personality shine. Flowy skirts, cropped tops, and laid-back rompers are perfect for those days when you want to look put together but feel like you’re still in your PJs—because who says comfort and style can’t be BFFs? And let’s not forget about layering: a cute jacket or oversized shirt thrown over your shoulders is the ultimate power move when you’re hopping from the sun to the shade.
Cool summer outfits aren’t just for flexing on your Insta feed—they’re also the ultimate go-to for gifting. Got a bestie with a birthday bash coming up? Or maybe you’re the queen of “just because” surprises? These picks are perfect for anyone who loves to stand out, stay comfy, and collect compliments like it’s their job. They’re also a lifesaver for those last-minute invites—think brunch dates, backyard BBQs, or that festival you totally forgot about until your group chat blew up. The best part? You don’t need a stylist or a trust fund to nail the look. With a little bit of creativity and a lot of attitude, you can mix and match pieces to create endless outfit combos that feel fresh every single time you wear them. Whether you’re shopping for yourself or playing fairy godmother for your squad, these pieces are designed to make you feel unstoppable. If you’re all about keeping things easy-breezy without sacrificing your style points, you’ll want to check out our handpicked edit of Comfortable Summer Outfits for even more inspo that’s equal parts chill and chic.
Every Windsor girl knows that the right outfit isn’t just about looking good—it’s about feeling like you can take on the world (or at least the dance floor). That’s why it’s worth thinking about the little details that make a big difference: adjustable straps for the perfect fit, breathable materials for those steamy days, and pockets—because who has time for a purse when you’re living your best life? Don’t be afraid to play with textures, mix unexpected prints, or add a statement accessory that turns heads. After all, fashion should be fun, fearless, and a little bit cheeky—just like you. So go ahead, treat yourself (or your bestie) to a wardrobe refresh that’s ready for every adventure. Whether you’re chasing sunsets, dancing under the stars, or just vibing with your favorite people, these cool summer outfits are here to make every moment a little more unforgettable.