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!
$64.90
A pink floral skater dress with a lace corset bodice and adjustable straps for a flattering fit.
$36.90
A pink ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$46.90
A lavender mini dress with floral sequin embellishments, tulle straps, and a lace-up back.
$39.90
An effortlessly chic white poplin mini dress with bow-trimmed straps and a flattering A-line silhouette.
$52.90
A white eyelet mini dress with a skater silhouette and flirty ruffled hem for festive occasions.
$39.90
A grey knit skater dress with a henley collared V-neckline and pleated silhouette.
$54.90
A floral ivory skater dress featuring a halter V-neckline and voluminous silhouette in poplin fabric.
$59.90
A charming red gingham skater dress featuring an open back, ruffled hem, and lace-trimmed neckline.
$42.90
A sleeveless sage satin mini dress with a pleated square neckline and skater silhouette.
$46.90
An adorably chic taupe skater dress with a plaid print and strapless sweetheart neckline.
$44.90
A denim skater dress featuring a corset bodice, sweetheart neckline, and tie-shoulder straps.
$49.90
A pink floral skater dress featuring a flirty lace-up back and ruffled short hem.
$26.90
A taupe plaid mini dress with a V-neckline, spaghetti straps, and a bodycon silhouette.
$25 $34.90 28% off
An elegant grey plaid mini dress with a strapless neckline and flirty pleated hem.
$42.90
A red gingham skater dress with lace trim and button details for a charming spring look.
$49.90
A light blue chiffon skater dress featuring a polka dot pattern and adjustable spaghetti straps.
$45.90
A natural floral skater dress with puff sleeves and a sweetheart neckline for a flattering silhouette.
$52.90
An ivory skater dress with puff sleeves, lace trim, and a playful bubble hem.
$54.90
A white eyelet lace midi dress with a square neckline, adjustable straps, and hidden side pockets.
$26.90
A preppy brown plaid skort with a high-rise belted waist and pleated A-line overlay.
$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.
$39.90
A black ribbed knit midi dress featuring a square neckline, side slit, and metal button accents.
$48.90
A pink mesh mini dress with faux pearl embellishments, featuring a bodycon silhouette and adjustable straps.
$39.90
A sleek pink satin A-line mini dress with a sweetheart neckline and asymmetric hem.
$64.90
A chic white bodycon dress with mesh fabric and faux pearl embellishments, perfect for formal events.
$46.90
A vibrant yellow skater dress with a ruffled skirt, halter tie-back, and smocked high waist.
$68.90
An ivory floral jacquard satin skater dress with a corset bodice and lace-up back.
$34.90
An ivory long sleeve dress with a ruched bust and flowy A-line silhouette in stretchy crepe.
$52.90
A strapless white mini dress with sequin bows and a satin lace-up back for a custom fit.
$48.90
A flirty white mini skater dress featuring a breezy eyelet knit and charming tie-back detail.
$39.90
A dainty white mini dress featuring sheer floral lace, ruffled puff sleeves, and a flattering empire waist.
$36.90
A black ditsy floral knit midi dress with a thigh-high slit and tie-front scoop neckline.
$52.90
A black floral mesh midi dress featuring a ruffle trim sweetheart neckline and adjustable spaghetti straps.
$59.90
A light blue strapless glitter party dress with a V-neckline, padded cups, and hidden pockets.
$32.90
A pink mini A-line dress with a flirty bust tie and stretchy knit fabric.
$46.90
A white strapless skater dress with a ruched bodice and playful pleated hem.
$39.90
A pink glitter knit skater dress with a strapless neckline and tiered ruffled hem.
$38.90
An ivory mini dress with a pleated bust, spaghetti straps, and an A-line silhouette.
$44.90
A strapless black lace and chiffon skater dress with a corset bodice and ruffle trim neckline.
$36.90
An olive rib knit bodycon mini dress with a playful front knot tie and asymmetrical hem.
$36.90
A pink mini dress with a pleated cowl neckline and stretchy knit fabric for comfortable wear.
$36.90
A green knit mini dress featuring a halter neckline, open back, and pleated sweetheart bust.
$19.97 $79.90 75% off
A floral chiffon babydoll dress in brown with a sweetheart neckline and flowy A-line silhouette.
$69.90
A light blue lace skater dress with a V-neckline, low-back, and hidden side pockets.
$32.90
A brown knit halter skater dress with ruched waist and flirty double-layered skirt.
$59.90
A natural floral skater dress with a strapless sweetheart neckline, lace trim, and charming bow.
$9.97 $42.90 77% off
A wine-colored off-the-shoulder skater dress with side ruching and an uneven hem in knit fabric.
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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: XL | 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: M | Knit 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
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: XS | Knit Fabric/Rhinestone/Satin 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 Black | Size: S | 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: L | Woven 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 Light Blue | 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
An adorable ditsy floral short dress for brunch, day dates, or celebration! The skater dress showcases a femme allure with a lace trim corset bodice designed to snatch your figure while the back bow tie and drop waist seam accentuate your figure. Pair with a ring set. Fit & FeaturesDitsy floral print, woven fabric, woven lining with lace trim, Lace trim sweetheart neckline, Adjustable shoulder straps, back zipper closure, Corset lace trim bodice, underwire bust, flexible boning, Drop waist seam, skater silhouette, Short-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunshine Bliss Ditsy Floral Lace Corset Skater Dress in Pink | Size: M | Woven Fabric
Preppy Dresses
As the sun peeks through the clouds and the days stretch a little longer, it's clear that spring is in full swing, and what better way to embrace this vibrant season than with a fresh take on preppy dresses? Whether you're picnicking in the park, attending a spring fling, or just looking to inject some classic charm into your everyday wardrobe, a preppy dress is a timeless choice that screams sophistication and fun. Picture yourself in a preppy white mini dress, the fabric light and breezy against your skin, as you laugh and twirl under the spring sun. These dresses aren't just garments; they're an instant mood booster and a nod to the playful days of yesteryear.
Now, let's talk versatility. Preppy dresses, with their clean lines and charming details, transition effortlessly from day to night. Imagine slipping into a black and white preppy dress for a day at the office or a casual business meeting. Pair it with a blazer and some smart loafers, and you're all set to make a professional yet stylish impression. As evening falls, swap the loafers for heels, ditch the blazer, and you're ready to catch up with friends at that chic little downtown bistro. The beauty of a preppy short dress lies in its ability to blend simplicity with a touch of elegance, making it perfect for those who appreciate styles that are both easy to wear and fashion-forward.
For those special spring and summer events, or just because you feel like treating yourself, exploring the array of preppy dresses available is like opening a treasure chest of style possibilities. From garden parties to graduation ceremonies, these dresses ensure you look polished and poised. And let's not forget about gifting - a carefully chosen preppy dress makes a thoughtful and stylish gift for the fashion-savvy women in your life, be it for a birthday, a special achievement, or just because. Want to see more delightful options? Dive into our collection of Pretty Mini Dresses and find the perfect blend of preppy and pretty for every occasion. Whether you're keeping it light with a breezy mini or going bold in striking patterns, remember that each dress tells a story. Make it yours, wear it with confidence, and watch as the world becomes your runway.