Cute Vacation Dresses
Pack your bags, babe, because the ultimate getaway just got a whole lot cuter with our collection of cute vacation dresses! Whether you're jet-setting to a tropical paradise or planning a chic city escape, these dresses are your passport to turning heads and stealing hearts. Designed for sunshine-filled days and dreamy sunset strolls, each piece is ready to make you feel like the main character in your own travel story. So slip into something fabulous and let those vacay vibes flow—adventure awaits, and you're dressed to impress!
$36.90
A denim satin mini dress with a ruched wrap silhouette and spaghetti straps for a chic look.
$32.90
A sultry pink mesh mini dress with adjustable straps and ruched seams for a chic night out.
$36.90
An elegant pink off-the-shoulder midi dress with a stretchy knit fabric and flared hem.
$59.90
A white mini dress with iridescent sequins, sheer velvet fabric, and adjustable spaghetti straps.
$40.90
A black glitter mini dress with a halter cowl neckline and tie-back spaghetti straps.
$37.90
A denim satin strapless mini dress with a pleated bust and flattering bodycon silhouette.
$46.90
A brown woven midi dress with a ditsy floral pattern, corset bodice, and high front slit.
$68.90
A chic mauve skater dress featuring floral jacquard satin, a corset bodice, and lace-up back.
$46.90
A vibrant yellow skater dress with a ruffled design, halter tie-back, and smocked high waist.
$44.90
A red glitter knit mini dress with a pleated cowl neckline and asymmetric wrap-front design.
$38.90
A white eyelet knit skater dress featuring a sleeveless square neckline and adjustable spaghetti straps.
$49.90
A sleeveless black skater dress featuring sheer lace, a V-neckline, and adjustable spaghetti straps.
$35.90
A pink sleeveless bodycon midi dress with a square neckline and stretchy knit fabric.
$19.97 $44.90 56% off
A white floral skater dress with a strappy tie-back and ruffled mini-length hem.
$59.90
A light blue woven midi dress featuring a corset bodice and charming lace-up back detail.
$48.90
A breezy white eyelet knit mini skater dress with a flirty tie-back and ruffled hem.
$36.90
A green knit mini dress featuring a halter neckline, pleated bust, and open back cutout.
$44.90
A gold metallic knit maxi dress featuring a plunge cowl halter neckline and adjustable strappy open back.
$36.90
A chic black mini dress with a pleated cowl neckline and flowy A-line silhouette.
$44.90
A strapless pink crepe mini dress with an A-line silhouette perfect for polished occasions.
$39.90
A brown mesh mini dress featuring a strapless neckline, side cutout, and ruffle-trim slit.
$20.97 $46.90 55% off
An abstract red knit maxi dress featuring a cowl neckline, hoop trims, strappy back, and high side slit.
$59.90
An ivory A-line maxi dress featuring gauze fabric, sheer lace insets, and a faux leather belt.
$34.90
A black rib-knit maxi dress featuring a crew neck and form-hugging, stretchy silhouette for versatile styling.
$42.90
A navy blue paisley skater dress with a halter V-neckline and playful tie-back design.
$39.90
A sheer white crochet knit cover-up dress with long sleeves, plunge neckline, and chic hoop insert.
$39.90
An eyelet lace mini dress in white with ruffled straps and a ruched sweetheart neckline.
$9.97 $42.90 77% off
A slate A-line mini dress with a V-neckline and ruffled hem in soft knit fabric.
$9.97 $56.90 82% off
An ivory floral skater mini dress with a sweetheart neckline and adjustable spaghetti straps.
$49.90
A brown mesh maxi dress featuring a bold floral print, cowl halter neckline, and curve-hugging fit.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$44.90
A taupe paisley skater dress with a halter V-neck and flowy mini-length hem.
$42.90
An ivory lace mini dress featuring a tie-front bust, ruffled hem, and adjustable spaghetti straps.
$9.97 $37.90 74% off
An alluring ivory floral bodycon mini dress with a strapless neckline and flirty ruffled hem.
$38.90
A vibrant pink mini dress featuring a leopard snake print, mesh fabric, side cutout, and ruffled slit.
$9.97 $46.90 79% off
A blue gauze skater dress featuring a halter neckline, cutout bodice, and ruffled mini hem.
$19.97 $39.90 50% off
A natural paisley-print maxi dress in mesh with a bodycon fit, square neckline, and high side slit.
$9.97 $49.90 80% off
A strapless ivory floral skater dress with a flirty ruffled hem in woven fabric.
$36.90
A heather grey knit mini dress with an off-the-shoulder neckline and A-line silhouette.
$19.97 $34.90 43% off
A yellow striped knit mini dress featuring a twisted strapless neckline and flattering bodycon silhouette.
$36.90
A black nylon mini dress featuring a fitted A-line silhouette, square neckline, and hidden shorts.
$38.90
A black mesh-lined bodycon mini dress featuring short puff sleeves, a sweetheart neckline, and side cutouts.
$44.90
A green mini dress with a sleeveless square neckline, cap-like sleeves, and ruched detailing.
$46.90
An adorably chic taupe skater dress with a plaid print and strapless sweetheart neckline.
$32.90
A wine-colored knit mini dress with a halter neckline and flirty cutout bodice.
$52.90
A pink skater dress with puff sleeves, lace trim, and a playful bubble hem.
$25 $34.90 28% off
A grey plaid strapless mini dress with a pleated hem and form-hugging knit fabric.
$89.90
A playful pink A-line short dress featuring lace trim, adjustable straps, and hidden side pockets.
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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
Cute Vacation Dresses
When it comes to curating the ultimate travel wardrobe, cute vacation dresses are the secret weapon every Windsor girl needs in her suitcase. Imagine breezing through sun-drenched boardwalks, hopping from dreamy beach brunches to rooftop soirées, or twirling under city lights in a dress that practically screams “main character energy.” Whether you’re planning a spontaneous girls’ getaway, a romantic escape, or just want to look fire for those endless photo ops, the right vacation dress is more than just an outfit—it’s your ticket to feeling unstoppable wherever the adventure takes you. These dresses are all about easy, throw-on-and-go vibes that still serve major style, letting you pack light without ever sacrificing your look. Think flowy silhouettes that catch every breeze, playful prints that pop against golden skin, and details like smocked bodices, open backs, or flirty cutouts that are just begging for a little trouble. And because we know not every Windsor girl is about the frills, you’ll find plenty of not girly vacation dress options—think sleek slip dresses, edgy shirt dresses, or minimalist wrap styles that deliver confidence with a side of sass.
Shopping for dresses for vacation is all about embracing your inner jetsetter and making every day feel like a new adventure. Maybe you’re the friend who plans every itinerary down to the minute, or maybe you’re the spontaneous soul who says “yes” to every last-minute invite—either way, your dress should be as ready for anything as you are. Lightweight fabrics are a must for those days when the sun is relentless and the only thing on your agenda is soaking up good vibes. Look for easy-care materials that resist wrinkles, so you can toss your dress in your bag and still look put together when you land. If you’re gifting, vacation dresses are a killer pick for birthdays, bachelorette parties, or just because your bestie deserves to feel like a goddess on her next trip. They’re the ultimate “I saw this and thought of you” present, perfect for anyone who lives for travel, adventure, and turning every sidewalk into a runway. And let’s be real: there’s nothing like that first twirl in a new dress to set the tone for an unforgettable trip.
No matter your destination or vibe, Windsor vacation dresses are designed to keep up with your wildest plans. From sunrise coffee runs to moonlit dance floors, these styles are made for making memories—and looking flawless while you do it. If you’re all about that effortless, lived-in glam, don’t miss our collection of Casual Vacation Dresses for even more inspo on how to keep things cute and comfy from takeoff to touchdown. Whether you’re hunting for spring vacation dresses to kick off your next escape or just want to refresh your travel lineup with pieces that work just as well at home as they do abroad, Windsor has your back. Pack your bags, cue the playlist, and get ready to make every moment a little more iconic—because with the right dress, you’re not just on vacation, you’re on a Windsor vacation.