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!
$36.90
A pink ribbed knit skater dress with an off-the-shoulder neckline and long fitted sleeves.
$76.90
A blush glitter mini dress with a strapless neckline, pleats, and a dramatic bow train.
$24.97 $54.90 55% off
A floral ivory skater dress featuring a halter V-neckline and voluminous silhouette in poplin fabric.
$52.90
An ivory skater dress with puff sleeves, lace trim, and a playful bubble hem.
$32.90
An adorable pink strapless mini dress with pleated bust and flowy A-line silhouette in stretchy knit.
$68.90
An ivory floral jacquard satin skater dress with a corset bodice and lace-up back.
$42.90
A sleeveless sage satin mini dress with a pleated square neckline and skater silhouette.
$59.90
A charming red gingham skater dress featuring an open back, ruffled hem, and sweetheart neckline.
$19.97 $44.90 56% off
A denim skater dress featuring a corset bodice, sweetheart neckline, and tie-shoulder straps.
$42.90
A red gingham skater dress with lace trim and button details for a charming spring look.
$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 side slit.
$46.90
An adorably chic taupe skater dress with a plaid print and strapless sweetheart neckline.
$25 $34.90 28% off
An elegant grey plaid mini dress with a strapless neckline and flirty pleated hem.
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$36.90
An elegant off-the-shoulder natural midi dress with a stretchy knit fabric and flared hem.
$29.97 $64.90 54% off
A chic white bodycon dress with mesh fabric and faux pearl embellishments, perfect for formal events.
$52.90
A strapless white mini dress with sequin bows and a satin lace-up back on mesh fabric.
$39.90
A pink satin strapless mini dress with a pleated A-line silhouette and back zipper closure.
$38.90
An ivory mini dress with a pleated bust, spaghetti straps, and an A-line silhouette.
$46.90
A lavender mini dress with floral sequin embellishments, tulle straps, and a lace-up back.
$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.
$23.97 $52.90 55% off
A black floral mesh midi dress featuring a ruffle trim sweetheart neckline and adjustable spaghetti straps.
$39.90
A white lace mini dress with ruffled puff sleeves, square neckline, and flattering A-line silhouette.
$59.90
A light blue strapless glitter party dress with a V-neckline, padded cups, and hidden pockets.
$42.90
A strapless pink lace skater dress with ruffled hem, perfect for a flirty night out.
$20.97 $46.90 55% off
A white strapless skater dress with a ruched bodice and playful pleated hem.
$36.90
A pink mini dress with a pleated cowl neckline and stretchy knit fabric for comfortable wear.
$39.90
A pink glitter knit skater dress with a strapless neckline and tiered ruffled hem.
$19.97 $44.90 56% off
A strapless black lace and chiffon skater dress with a corset bodice and ruffle trim neckline.
$19.97 $42.90 53% off
A pink sleeveless skater dress with a ruffled silhouette and square neckline, perfect for brunch.
$36.90
A green knit mini dress featuring a halter neckline, pleated bust, and open back cutout.
$28.97 $64.90 55% off
A pink skater dress with a lace-trim corset bodice and flattering short-length hem.
$49.90
A light blue satin skater dress with a floral pattern and corset bodice for a coquette vibe.
$20.97 $46.90 55% off
An ivory chiffon skater dress featuring a smocked bodice, cutout accent, and breezy long sleeves.
$59.90
A natural floral skater dress with a strapless sweetheart neckline, lace trim, and charming bow.
$19.97 $32.90 39% off
A brown knit halter skater dress with ruched waist and a flirty double-layered skirt.
$79.90
A navy blue sequin satin A-line dress with a lace-up back and adjustable spaghetti straps.
$52.90
A white eyelet lace skater dress featuring a scoop neckline and ruffled mini-length hem.
$36.90
A sage ribbed knit mini dress with a scoop neckline and flattering skater silhouette.
$69.90
A sage skater dress featuring a glitter mesh fabric, corset-style bodice, and tiered ruffled design.
$69.90
A blue floral mesh skater dress with a sweetheart neckline and tiered ruffled skirt.
$26.90
A black plaid pleated micro skort with a belted waist and hidden shorts for a preppy look.
$44.90
A dazzling blue sequin mini dress with a sweetheart neckline and adjustable spaghetti straps.
$39.90
An eyelet lace mini dress with ruffled straps and a ruched sweetheart neckline in white.
$89.90
A pink beaded mesh A-line mini dress with a sweetheart neckline and adjustable spaghetti straps.
$22.97 $49.90 54% off
A chic off-white woven mini dress featuring a corset bodice and sleeveless sweetheart neckline.
Now Trending
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
Preppy Dresses
When you’re living for that main character energy, nothing delivers quite like preppy dresses. Whether you’re channeling classic campus vibes, brunching with your besties, or plotting your next Insta-worthy adventure, a preppy dress is your instant ticket to polished perfection. These looks are all about clean lines, playful details, and that just-right mix of sweet and sassy. Think crisp collars, pleated skirts, and patterns that pop—like stripes, plaids, or those adorable little prints that make you feel like you’re walking straight out of a rom-com. The best part? Dresses preppy enough to turn heads don’t have to be reserved for any one crowd. They’re made for the girl who loves to blend timeless style with a little bit of edge, the friend who’s always first to RSVP yes, and even the little sister who’s just starting to build her own signature style. If you’re shopping for a gift, a preppy dress is basically the ultimate “I get you” present—perfect for graduations, birthdays, or just because your BFF deserves to feel like a total icon.
Choosing a preppy dress is all about playing up your personality and making it your own. Maybe you’re into that preppy black dress moment—sleek, sophisticated, and always in style, ready to take you from a coffee date to a rooftop party without missing a beat. Or maybe you’re obsessed with preppy styles dresses that bring a little extra fun, like a flirty bow detail or a skirt that twirls just right. The versatility is next-level: dress them up with pearls and ballet flats, or go full cool-girl with chunky sneakers and a denim jacket. And don’t even get us started on the power of layering—a crisp button-down under your favorite mini, a cozy cardigan draped over your shoulders, or a statement headband that ties it all together. Every detail is a chance to show off your unique vibe. If you’re all about those Pretty Little Liars or Gossip Girl feels, preppy dresses are your secret weapon for nailing that effortlessly put-together look, no matter where the day takes you.
The magic of preppy dresses is that they’re never one-size-fits-all—they’re made for mixing, matching, and making memories. Picture yourself strutting into a garden party with a pleated mini that catches the sunlight, or acing your next presentation in a tailored shift that says “I’ve got this” before you even speak. These dresses are designed for those moments when you want to feel confident, comfortable, and ready for anything. And if you’re on the hunt for that perfect mini with just the right amount of preppy flair, don’t miss the curated collection at Pretty Mini Dresses—your new faves are waiting to make every day a little more iconic. With preppy styles dresses, you’re not just getting dressed—you’re setting the tone, making the memory, and owning every room you walk into.