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.

  • Simple And Chic Ponte Knit Mini Skort

    Simple and chic, this ponte knit mini skort will elevate your casual looks. It features a mid-rise waist, a mini-length overlay with a double slit design, and hidden shorts for coverage.

    Fit & Features

    • Ponte knit fabric, moderate stretch
    • Mid-rise waist
    • Mini-length overlay
    • Double slit side design
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000066

    Category Name: Vacation Looks

    Price: $27.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Spring Vibes Daisy Studded Jelly Tote Bag

    This adorable jelly tote bag is the perfect accessory for your fab spring festivities! Made with a trendy jelly material, this tote features a small rectangular design with adorable daisy-studded accents. Includes two top handle straps and a removable long chain-link shoulder strap. Style with a flowy skater dress and heels for weekend brunch!

    Fit & Features

    • Jelly material
    • Small rectangular design
    • Small daisy-studded accents
    • Dual top handle straps
    • Foldover with snap-button closure
    • Removable chain-link shoulder strap, lobster clasps

    Style Number/Barcode: 07203-1983

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time For Vacay High Rise Tropical Palazzo Pants

    These tropical palazzo pants are ready for your next vacay! Features a high-rise waist and wide-leg silhouette for a flattering fit. The palm print on knit fabric adds a touch of paradise to any outfit. Complete the look with the matching top.

    Shop Matching Top: Time For Vacay Tie Front Tropical Crop Top

    Fit & Features

    • Palm print, stretchy knit fabric
    • High rise waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2482

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Bound Cutout Tropical Mesh Midi Dress

    You'll be ready for your trip with this tropical mesh midi dress! This dress features a square neckline, spaghetti straps, and a bodycon fit for a flattering silhouette. The side cutout drawstring adds a touch of fun while the side slit and midi-length offer a sultry feel. Complete the look in trendy sandals.

    Fit & Features

    • Tropical palm leaf print
    • Mesh fabric, stretchy knit lining
    • Spaghetti straps
    • Square neckline
    • Side cutout drawstring
    • Bodycon fit, side slit
    • Runs true to size

    Style Number/Barcode: 05102-5710

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing Sunshine Crochet Wedges

    These crochet wedge mules serve beachy vibes with an elevated twist, perfect for brunch, shower celebrations, or dinners al fresco.

    Fit & Features

    • Square toe
    • Wide strap
    • Wedge sole
    • Crochet material
    • Runs true to size

    Style Number/Barcode: 07406-000028

    Category Name: Vacation Looks

    Price: $45.90

    Availability: In Stock

    Available Color: NUDE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Chic Muse Watercolor Tie-Front Crop Top

    Showcase your iconic style like the chic muse you are in this printed tie-front crop top! Crafted from a breezy woven fabric, it is detailed with a gorgeous watercolor print for a mesmerizing look. The top features a sleeveless V-neckline with a tie-front design at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a fitted cropped hem. Style with the matching midi skirt and espadrille wedges for a sunset dinner!

    Shop Matching Bottoms: Chic Muse Watercolor Wrap-Slit Midi Skirt

    Fit & Features

    • Watercolor print
    • Woven fabric
    • V-neckline, tie-front
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2518

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Fling Heart-Shaped Sunglasses

    Flirt up a storm in these adorable heart-shaped sunglasses perfect for the summer season! Featuring the cutest heart-shaped design with tinted lenses, these shades have a sleek thin metal frame with thin arms, a thin metal nose bridge, and rubber nose pads for support. Style with hoop earrings for a music festival!

    Fit & Features

    • Heart-shaped design
    • Tinted lenses
    • Thin metal frame and arms
    • Thin metal nose bridge
    • Rubber nose pads
    • 100% UV protection

    Style Number/Barcode: 07008-1048

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute Gaze Chain Trim Cat Eye Sunglasses

    Slip on these cat eye sunglasses knowing you're the cutest babe around! The chain trim arms add a touch of edge while the tinted lenses help protect your eyes from the sun.

    Fit & Features

    • Chain trim arms
    • Cat eye shaped frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1134

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cool Girl Chic Strapless Abstract Mesh Mini Dress

    Keep your going-out look cool girl chic with this sultry strapless abstract mesh mini dress. The airy sheer mesh fabric showcases a trendy abstract print and includes a full-length soft knit lining for coverage. The strapless straight-across neckline features an elastic band for a stretchy and secure fit, while the bodycon silhouette will flaunt your stunning curves. Style this short dress with a layered necklace and lace-up heels for drinks with the girls!

    Fit & Features

    • Stretchy sheer mesh fabric with soft knit lining
    • Abstract print
    • Strapless straight elasticized neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5558

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Reputation Halter Cutout Ribbed Knit Midi Dress

    It's easy to keep up with your stylish reputation with this ribbed knit midi dress! Perfect for vacation or weekend plans, this midi dress boasts a trendy halter neckline with tie straps, sultry side, and back cutouts that flaunt some skin, and a bodycon silhouette adorned with a front slit. Complete the look with sunglasses and a cute purse!

    Fit & Features

    • Ribbed knit fabric, moderate stretch
    • Halter neckline with tie straps
    • Cutout side and back
    • Front slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2000

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • 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