Vacation Looks

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Vacation Dresses & Outfits for Effortless Getaways

Pack light and look luxe in vacay dresses and vacation outfits designed for sun-soaked escapes. Whether you’re poolside at a beach resort or exploring cobblestone streets, Windsor’s resortwear blends breezy fabrics, relaxed silhouettes, and bold prints for travel outfits you’ll want to wear on repeat.

Easy, Packable Styles

Slip into breezy maxi dresses in tropical prints or neutral tones—white, ivory, and tan—for instant cruisewear elegance. Chic rompers and vacay outfits like matching top-and-bottom sets in airy cotton or linen make packing a breeze and styling stress-free.

Day-to-Night Versatility

Transition from sunrise yoga to sunset cocktails in flowy sundresses or relaxed separates. Mix and match colorful vacation-ready separates—think high-waist shorts with off-shoulder tops—or choose effortless travel outfits in knit jumpsuits and wrap skirts that go anywhere.

Resort & Beach Essentials

Complete your look with stylish bikinis under sheer cover-up dresses or mesh tunics. Add slide sandals, statement sunglasses, and a woven tote for poolside chic. From beach days to rooftop lounges, these vacay dresses keep you feeling confident and carefree.

Ready to jet off in style? Explore Windsor’s full collection of vacation dresses and outfits online, in-app, or at your nearest Windsor store.

  • Shine Shocker Rhinestone Strappy Flat Sandals

    Step into the spotlight in these rhinestone strappy flat sandals at parties or on vacation! These stunning sandals feature a round toe with a metallic strap, along with rhinestone embellished asymmetrical straps for a touch of sparkle. The closed metallic ankle with a zipper closure and adjustable ankle strap with buckle provide the perfect fit for all-day comfort. Complete the look in a cute romper or jumpsuit.

    Fit & Features

    • Flat sole, faux leather material
    • Round toe with metallic strap
    • Rhinestone embellished straps
    • Closed ankle with zipper closure
    • Adjustable ankle strap with buckle
    • Runs true to size

    Style Number/Barcode: 07404-1191

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Oasis Halter Crochet Crop Top

    Keep things trendy on vacation in this crochet crop top and inspire your mermaid core aesthetic!  The halter neckline and spaghetti strap tie provide a flattering fit, while the padded bra cups offer support. Featuring a cropped hem and open back with tie closure, this top is perfect for adding a touch of style. Complete the look in a denim midi skirt and sandals!

    Fit & Features

    • Non-stretch crochet fabric
    • Halter neckline, spaghetti strap ties
    • Padded bra cups
    • Open back with tie closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06005-1973

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Life Twist Eyelet Lace Skater Romper

    Life's so sweet in this eyelet lace skater romper for spring-to-summer fun! With a flattering V-neckline and delicate twist detail, this romper will elevate your everyday style. Spaghetti straps and a keyhole cutout add a touch of flirty charm, while the skater silhouette gives you a flattering look. Style this romper with sandals and sunnies!

    Fit & Features

    • Eyelet lace fabric, knit stretchy lining
    • Spagehtti straps
    • Twist and keyhole cutout
    • Skater silhouette, shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-1121

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Perfection Rhinestone Butterfly Metallic Sandals

    These stunning rhinestone butterfly metallic sandals are glam perfection! Designed with a faux leather material with a trendy metallic sheen, these sandals feature an almond-shaped toe with a thong strap design and an adjustable ankle strap for a customized fit. The straps are accented with glimmering rhinestone-adorned butterfly accents and sparkling rhinestone embellishments for an enchanting dressy vibe. Include a sleek back adjustable chain with a lobster clasp closure. Style with a charm necklace!

    Fit & Features

    • Faux leather material with metallic sheen
    • Almond toe, thong strap design
    • Adjustable ankle strap with buckle closure
    • Rhinestone butterfly accents, rhinestone embellishments
    • Back adjustable chain with lobster clasp closure
    • Flat sole, slightly cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1180

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Breeze Printed Dual-Slit Maxi Skirt

    Capture the breezy tropical vibes in this flowy printed dual-slit maxi skirt! The lightweight stretchy knit fabric showcases a tropical palm leaf print for an iconic poolside look on your dreamy vacay. It features a flattering high-rise elasticized waistband, a built-in cheeky lining, dual high front slits to bare some skin, and a maxi-length hem. Style with a crop top and strappy sandals.

    Fit & Features

    • Tropical print
    • Stretchy knit fabric
    • High-rise elasticized waist
    • Built-in cheeky underwear lining
    • Dual high front slits
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-0974

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living In The Palms Tie-Front Crop Top

    Escape to a tropical island in this breezy palm print crop top perfect for dinners with a view or exploring with a cocktail in hand! This top has flirty dolman short sleeves and a tie-front design along the cropped hem on stretchy knit palm print fabric. Complete the look with the matching pants.

    Shop Matching Bottoms: Living In The Palms Wide Leg Palazzo Pants

    Fit & Features

    • Palm print, stretchy knit fabric
    • Dolman short sleeves
    • Tie-front 
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-0450

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ray Of Beauty Lace-Up Corset Skater Dress

    You'll be a ray of beauty in this chic lace-up corset skater dress! Designed with an alluring corset-style bodice and the cutest fit-and-flare silhouette, you'll give off a flirtatious vibe.

    Fit & Features

    • Cotton woven fabric, stretchy knit lining
    • Corset bodice, ruched sweetheart neckline, tie-front bust
    • Thin adjustable tank straps
    • Lace-up strappy back, tie closure
    • Side zipper with hook-eye closure, side pockets
    • Short fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4061

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glittery Vibes Ruched Spaghetti Strap Crop Top

    Bring on the glittery vibes for your next girl's night in this ruched crop top! Designed with a glitzy glitter knit fabric, this crop top is glam perfection. It features a sleeveless scoop neckline with ruching for an alluring detail, built-in padded cups so you don't need to wear a bra, spaghetti straps, and an ultra-cropped hem with a form-hugging fit for a sultry slay. Complete your going-out look with the matching maxi skirt and clear heels!

    Shop Matching Bottoms: Glittery Vibes High Slit Maxi Skirt

    Fit & Features

    • Textured glitter knit fabric, front lining
    • Plenty of stretch
    • Sleeveless scoop neckline with ruching
    • Padded bust
    • Spaghetti straps
    • Ultra-cropped hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-5023

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Perfection Scoop Neck Bow Skater Dress

    You'll look like cute perfection in this sleeveless skater dress at soirees! With adjustable spaghetti straps, a flattering scoop neckline, and three adorable bows with ruffle trim, this skater dress will have you feeling confident and stylish in its short-length hem. Complete the look in trendy sandals and a hair accessory.

    Fit & Features

    • Airy chiffon fabric, woven lining, no stretch
    • Adjustable spaghetti straps
    • Scoop neckline
    • Back zipper and hook-eye closure 
    • Three bows with ruffle trim
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3453

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Attention Collared Cargo Mini Dress

    Capture all the attention in this structured and chic cargo mini dress! It features a sleeveless collared neckline, a complete zip-front design creating a V-neckline, a faux belted waist, large cargo-style side pockets, a mini-length hem, and a streamlined form-hugging fit. The woven fabric offers minimal stretch. Style this mini dress with hoop earrings and clear heels.

    Fit & Features

    • Sleeveless collared neckline
    • Complete zip-front, V-neckline
    • Faux belted waist, large cargo side pockets
    • Mini-length hem
    • Form-hugging fit
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5103

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Notice Me Lace Ruffle Mini Dress

    Make 'em' stop and stare at you in this lace mini dress as the chic bride-to-be or gorgeous graduate! The dress features a sleeveless V-neckline, adjustable spaghetti straps that crisscross along the back, a form-hugging fit, and a flirty asymmetrical ruffle trim hem. Complete the look in block heel sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Crisscross back
    • Form-hugging fit
    • Ruffle trim mini-length hem
    • Lace fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2637

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Piece One-Shoulder Hoop Bodysuit

    The perfect sleeveless bodysuit to dress up your favorite bottoms! This sleek and form-hugging bodysuit features a one-shoulder neckline and tank strap with a trendy hoop insert so you can strut with confidence everywhere you go. Complete the look in high rise jeans and heels.

    Fit & Features

    • Knit double-lined fabric, moderate stretch
    • One-shoulder neckline
    • Tank strap with hoop insert
    • Form-hugging fit
    • Thong bottom, snap-button closures
    • Runs true to size

    Style Number/Barcode: 06001-5357

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out In The Wild Leopard Crop Top

    You could chill… but why would you? This halter top is made for turning heads with a draped cowl neckline and chainlink moment that screams “she knows she’s the vibe.”

    Fit & Features

    • Leopard print, stretchy mesh knit fabric
    • Cowl halter neckline, hoop inserts, spaghetti strap tie
    • Open back with spaghetti strap tie
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000198

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Glam Rhinestone Twisted Thong Strap Sandals

    These rhinestone thong strap faux leather sandals will add a casual glam vibe to your fave 'fits! They feature an open almond-shaped toe, a trendy twisted thong strap design, an adjustable ankle strap with a buckle closure, and mini rhinestone embellishments for a glitzy sparkle. The flat padded sole offers comfortable wear. Style with a rhinestone ring set.

    Fit & Features

    • Faux leather upper
    • Almond toe
    • Twisted thong strap design
    • Adjustable ankle strap with buckle closure
    • Mini rhinestones
    • Luxe fit cushion insole
    • Runs true to size

    Style Number/Barcode: 07404-1162

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Lowkey Hoops

    Downplay the drama with some simple lowkey hoop earrings. With their thin etched design and easy latch closure, they provide comfortable wear. A definite must-have for happy hour with your girls! Wear them with a flirty midi dress and some trendy clear mules.

    Fit & Features

    • Dainty textured shimmer design
    • Latch closure

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0113

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Night Moves Sequin Mini Skirt

    Own the night in this dazzling sequin mini skirt for a chic shimmer!

    Fit & Features

    • Sequin embellished
    • Low-rise waist
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0749

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Style Zebra Print Crop Top

    Show off a wild style in this trendy zebra print crop top! It features a sleeveless halter neckline with tie-back spaghetti straps, an angled cropped hem, and a form-hugging fit. Complete the look with the matching mini skirt and pair of clear heels.

    Shop Matching Bottoms: Wild Style Zebra Print Mini Skirt

    Fit & Features

    • Sleeveless halter neckline
    • Tie-back spaghetti straps
    • Angled cropped hem
    • Form-hugging fit
    • Zebra print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4697

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Floral Knit Maxi Dress

    Showcase your beauty as the best-dressed wedding guest in this blooming floral knit maxi dress! Designed with a gorgeous floral print design, it features a sleeveless V-neckline, spaghetti straps that lead to a bold open back with a lace-up strappy design, a thigh-high front slit to show off your heels, and a slim-fit silhouette. Complete your look with sleek hoop earrings.

    Fit & Features

    • Floral printed knit fabric
    • V-neckline, spaghetti straps
    • Open back, cross-back lace-up straps
    • Fitted floor-length skirt
    • High front slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05101-0851

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Resort Paradise Crochet Open Back Maxi Dress

    Escaping to a resort paradise? You're going to need this crochet maxi dress to give you the perfect getaway vibes! It features a sleeveless crew neckline, an open back design that turns heads, and a form-hugging maxi silhouette with dual side slit accents. Complete the look with sandals and your favorite sunnies!

    Fit & Features

    • Sleeveless crew neckline
    • Open back design
    • Form-hugging silhouette
    • Maxi-length, dual side slit accents
    • Sheer crochet fabric
    • Runs true to size

    Style Number/Barcode: 06005-1829

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Island Time Strapless Floral Romper

    This strapless romper exudes carefree vibes, perfect for vacations! The strapless neckline and form-hugging fit accentuate your curves, while the statement floral print adds a touch of tropical essence.

    Fit & Features

    • Stretchy knit fabric, statement floral print
    • Strapless neckline
    • Form-hugging fit
    • Ruffled hem, fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000053

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Iconic Basic Cap Sleeve Midi Dress

    An iconic basic midi dress your closet needs! Create effortlessly chic looks with this knit dress featuring cap sleeves, a V-neck, and a bodycon silhouette with a curved hemline on brushed stretchy fabric. Style with slide sandals and sunglasses for hanging downtown with friends!

    Fit & Features

    • Cap sleeves
    • V-neck
    • Bodycon silhouette
    • Curved midi-length hemline
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-2530

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Card Leopard Floral Print Maxi Skirt

    This skirt’s got plot twist energy—sweet florals meet fierce leopard in a ruffled maxi made for your wild side. Let the bold print and thigh-high slit steal the spotlight from brunch to beach nights.

    Fit & Features

    • Sheer mesh fabric with mini-length knit lining, high stretch
    • Leopard and floral multi-print pattern
    • High-rise waist
    • Ruching, hip-hugging fit
    • Thigh-high side slit, ruffled hem
    • Maxi-length hem, flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000061

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Fling Heart-Shaped Sunglasses

    Flirt up a storm in these adorable heart-shaped sunglasses perf for the summer season. They feature a heart-shaped design with no frame, pink gradient-tinted lenses, sleek metal arms, and rubber nose pads for support. Style with rhinestone hoops.

    Fit & Features

    • Heart-shaped design, no frame
    • Pink gradient-tinted lenses
    • Thin metal arms
    • Rubber nose pads
    • 100% UV protection

    Style Number/Barcode: 07008-1036

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Cute Energy Strapless Paisley Satin Crop Top

    This paisley satin crop top is the easiest way to add a cute boho vibe to your look! The strapless neckline and tie-back closure provide a flattering fit, while the stretchy smocked lining offers comfort and the crop hem flaunts your figure. Complete the look in cute jean shorts and sandals.

    Fit & Features

    • Paisley print, satin fabric, stretchy smocked lining
    • Strapless neckline
    • Tie-back closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2550

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale