Preppy Dresses
Get ready to channel your inner Blair Waldorf with a collection of preppy dresses that scream sophistication with a cheeky twist! Whether you're strutting through campus or brunching with the squad, these styles are all about crisp lines, playful patterns, and timeless elegance. Think classic meets modern with a dash of fearless flair. From pleated skirts to tailored silhouettes, each dress is your ticket to turning heads and setting trends. So go ahead, unleash your preppy persona and let those good vibes roll!
$44.90
A green gingham mini dress with a smocked design, ruffled trim, and adjustable spaghetti straps.
$25 $34.90 28% off
An elegant grey plaid mini dress with a strapless neckline and flirty pleated hem.
$36.90
An elegant off-the-shoulder natural midi dress with a stretchy knit fabric and flared hem.
$38.90
An ivory mini dress with a pleated bust, spaghetti straps, and an A-line silhouette.
$36.90
A green knit mini dress featuring a halter neckline, pleated bust, and open back cutout.
$42.90
A strapless pink lace skater dress with ruffled hem, perfect for a flirty night out.
$44.90
A dazzling blue sequin mini dress with a sweetheart neckline and adjustable spaghetti straps.
$20.97 $46.90 55% off
A pink knit skater dress featuring a pleated mini hem, scoop neckline, and trendy cutout back.
$68.90
An ivory satin skater dress with floral jacquard, corset bodice, and lace-up back design.
$9.97 $59.90 83% off
A charming red gingham skater dress featuring an open back, ruffled hem, and lace-trimmed neckline.
$46.90
An adorably chic taupe skater dress with a plaid print and strapless sweetheart neckline.
$52.90
An ivory skater dress with puff sleeves, lace trim, and a playful bubble hem.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a side slit.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$32.90
A pink strapless A-line mini dress with pleated bust and stretchy knit fabric for chic occasions.
$46.90
A vibrant yellow skater dress with a ruffled skirt and halter tie-back straps for sunset outings.
$36.90
A sage satin skater dress with a V-neckline, halter strap, and flirty fit-and-flare silhouette.
$48.90
A flirty white mini skater dress featuring a breezy eyelet knit and charming tie-back detail.
$59.90
A light blue strapless glitter party dress with a V-neckline, padded cups, and hidden pockets.
$32.90
A breezy white eyelet knit skater dress featuring a square neckline and double-layered flared skirt.
$69.90
A pink satin skater dress featuring a lace-up back, corset bodice, and bow tie shoulder straps.
$36.90
A light blue glitter knit skater dress with a strapless neckline and uneven mini-length hem.
$79.90
A navy blue sequin satin A-line dress with adjustable straps and an eye-catching lace-up back.
$69.90
A sage skater dress featuring a glitter mesh fabric, corset-style bodice, and tiered ruffled design.
$39.90
An eyelet lace mini dress with ruffled straps and a ruched sweetheart neckline in white.
$22.97 $49.90 54% off
A white cotton gauze mini dress featuring cherry embroidery, a plunge halter neckline, and a skater silhouette.
$44.90
A taupe paisley skater dress with a halter V-neck and flowy mini-length hem.
$39.90
A high-rise black knit skort with a preppy pleated silhouette and striped mini-length hem.
$44.90
A green mini dress featuring a sleeveless square neckline, cap-like sleeves, and flattering ruching.
$29.90
A trendy brown striped knit mini dress with a mock neckline and long fitted sleeves.
$21 $29.90 30% off
An adorable charcoal plaid mini dress with sheer lace trims and a chic center bow detail.
$39.90
A chic black crepe mini dress featuring a strapless foldover neckline and flattering skater silhouette.
$39.90
A white rib knit mini dress with a chic collar, short sleeves, and a flirty side slit.
$89.90
A playful pink A-line short dress featuring lace trim, adjustable straps, and hidden side pockets.
$19.97 $33.90 41% off
A chic ivory satin skater dress featuring a flattering sweetheart neckline and twirl-worthy silhouette.
$44.90
An ivory satin skater dress featuring a square neckline, ruched bust, and adjustable shoulder straps.
$49.90
An airy white eyelet skater dress featuring a lace-up bust, lace trim, and adjustable tank straps.
$35.90
A burgundy plaid mini dress with lace trim, spaghetti straps, and a form-hugging silhouette.
$59.90
A pink woven mini dress featuring a tie-front design, pleated hem, and spaghetti strap ties.
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This adorable strapless A-line mini dress is so your vibe! Designed with a stretchy lined knit fabric, it features a strapless straight-across neckline, chic pleated detailing at the bust, and a flirty flowy A-line silhouette on the mini-length hem. Style for a girl's night with statement earrings and strappy mules. Fit & FeaturesStretchy knit fabric with knit lining, Strapless straight neckline, no-slip strip, Pleated bust, A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor So Your Vibe Strapless A-line Mini Dress in Light Blue | Size: L | Knit Fabric
Bring on the cute attitude in this ponte mini skort brings featuring a flattering high-rise waist, and a skirt overlay designed with dual front slits along the form-hugging fit. Fit & FeaturesSmooth ponte knit fabric, minimal stretch, High-rise waist, Skirt overlay, dual front slits, Form-hugging silhouette, Mini-length hem, Shorts lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cute Attitude Ponte Slit Mini Skort in Black | Size: L | Knit Fabric
A fashionista like you will adore this basic mini skirt for creating your day and night looks! Featuring an elasticized high-rise waistband, bodycon silhouette, and a flirty front hem slit on stretchy and smooth knit fabric. Style with a corset top and heels. Fit & FeaturesHigh-rise elasticized waistband, Bodycon silhouette, Front hem slit, Mini-length hem, Stretchy and smooth knit fabric, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Get Down With Basic Slit Mini Skirt in Black | Size: XS | Knit Fabric
This satin mini dress will be your favorite for celebrations, events, and date nights! Sleek and smooth satin shapes this off-the-shoulder dress, which features a flattering A-line silhouette perfect for styling with heels. Fit & FeaturesSmooth and sleek satin fabric, stretchy knit lining, Off-the-shoulder neckline, Short sleeve cuffs, A-line silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Classics Lover Off-The-Shoulder Satin A-Line Mini Dress in Pink | Size: S | Knit Fabric/Satin Fabric
A true showstopper of a mini dress perfect for adding a touch of sparkle to any occasion. The short-length rhinestone dress features a square neckline and adjustable spaghetti straps, while the A-line silhouette flatters your figure down to the uneven-cut hem. Complete the look in platform sandals for a dressy night out! Fit & FeaturesSleeveless square neckline, Adjustable spaghetti straps, Back zipper and hook-eye closure, A-line silhouette, Mini-length hem, uneven cut design, Rhinestone-embellished, mesh fabric, stretchy knit lining, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sparkling Perfection Rhinestone A-Line Mini Dress in Pink | Size: XS | Knit Fabric/Rhinestone/Mesh Fabric
Capture all the attention with your sultry allure in the Paige rhinestone formal bodycon mini dress! She features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, all-over rhinestone embellishments for that total glam girl vibe, a mini-length hem, and a bodycon silhouette to hug your gorgeous curves. The slinky knit fabric offers plenty of stretch. Style this mini dress with metallic heels for your next dressy night out! Fit & FeaturesSleeveless cowl neckline, Adjustable spaghetti straps, All-over rhinestone embellishments, Mini-length hem, bodycon silhouette, Slinky knit fabric, full-length knit lining, plenty of stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Paige Rhinestone Formal Bodycon Mini Dress in Light Blue | Size: M | Knit Fabric/Rhinestone
This chic side slit knit mini skirt will give you a fabulous fit and become a favorite in your closet! The ponte knit fabric offers a structured fit with moderate stretch. The high waist features an elasticized waistband for comfortable wear, while the mini-length hem and side slit accent will give that sultry flair. The bodycon silhouette will hug your gorgeous curves. Style this mini skirt with a basic bodysuit and ankle booties for happy hour. Fit & FeaturesPonte knit fabric, moderate stretch, High-rise elasticized waist, Mini-length hem, Asymmetric seam, side slit, Bodycon fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Fabulous Fit Side Slit Knit Mini Skirt in Black | Size: L | Knit Fabric
Windsor Brenda Low Back Bow Taffeta Skater Dress in Black
$19.97 $64.90
69% off
Chat, dance, and twirl the night away in the Brenda taffeta skater dress! The short dress is ready to party with a voluminous silhouette and a stunning low-cut back with a statement bow. Fit & FeaturesTaffeta fabric lined with tulle, stretchy knit fabric, Tank shoulder straps, Low back with bow, Skater silhouette, Short-length hem, Runs true to size, Where to Wear:Prom, brides, weddings, bridesmaids, fancy date nights, dinner parties, cocktail events Free Shipping on All Orders Over $75. | Windsor Brenda Low Back Bow Taffeta Skater Dress in Black | Size: XS | Knit Fabric
A sassy mini dress to slip on when the sun goes down and the beat is calling you to the dancefloor! This dress is featured in a sultry bodycon silhouette with a halter neckline accented with hoop inserts. Fit & FeaturesAbstract print, stretchy knit fabric, Cowl halter neckline, hoop accents, Bodycon silhouette, Mini-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sun Goes Down Halter Abstract Bodycon Mini Dress in Brown | Size: S | Knit Fabric
Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Yellow
$19.97 $32.90
39% off
Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette. Fit & FeaturesDouble-lined brushed knit fabric, moderate stretch, Strapless straight neckline, Ruched side seams, Bodycon silhouette, Mini-length tiered ruffled hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Here Comes The Sun Strapless Ruffled Mini Dress in Yellow | Size: L | Knit Fabric
Preppy Dresses
Ready to live your best main character life? Preppy dresses are basically the secret weapon in every Windsor girl’s closet—serving up that crisp, polished vibe with a wink and a twist. Think of them as the ultimate confidence booster, whether you’re heading to brunch with the squad, running the world at your internship, or just need to make a killer first impression at a new school or club. There’s something about a preppy dress that just pulls everything together—collared necklines, pleated skirts, sweet little bows, or a sharp blazer-inspired cut. It’s like you’re channeling your inner campus queen, but with a modern edge that says you know all the best places in town. And let’s be real, nothing says “I’ve got my life together” like a preppy black dress—timeless, versatile, and always ready for whatever your day (or night) throws at you. If you’re feeling a little more angelic, a white preppy dress is your ticket to looking fresh and flawless, whether you’re taking over the tennis courts or just want your Insta feed to pop.
Shopping for a preppy dress is all about finding those little details that make you feel unstoppable. Maybe you’re obsessed with a preppy mini dress that shows off your legs and lets you move like you own the place, or you want a style that’s a little more classic with a fit-and-flare silhouette that twirls just right. Don’t forget about fabric—crisp cottons, structured knits, or even a hint of stretch for those spontaneous dance breaks. If you’re gifting for your bestie, your sister, or even as a “just because” treat for yourself (because you deserve it, babe), a preppy dres is the kind of piece that instantly upgrades any wardrobe. Picture her unwrapping a box to find a dress that’s equal parts sweet and sophisticated—perfect for graduation parties, birthday brunches, or that all-important first day at a new job. It’s the kind of gift that says, “I see you, I love your style, and I know you’re about to turn heads.”
The best part? Preppy dresses are made for mixing, matching, and making your own rules. Layer one over a graphic tee for a little extra attitude, throw on a cropped cardigan for those late-night ice cream runs, or swap your sneakers for heels when you want to take things up a notch. Your preppy dress is your style playground—so have fun, break the rules, and don’t be afraid to stand out. And if you’re loving those flirty, leg-baring looks, check out the Pretty Mini Dresses collection for even more inspo. Whether you’re shopping for yourself or picking out the perfect gift, these dresses are all about bringing the good vibes, turning up your confidence, and making every moment a little more unforgettable.