Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Sweet Sun Floral Bikini Bottoms

    Enjoy the sweet sunshine at the pool or beach in these floral bikini bottoms! Pair with the matching bikini top.

    Fit & Features

    • Floral print, knit lined fabric
    • Low-rise waist
    • Ruffle trim
    • Cheeky bottom
    • Returns are not accepted without the hygienic liner
    • Runs true to size

     

    Shop The Matching Bikini Top: Sweet Sun Floral Tie-Front Bikini Top

    Style Number/Barcode: 07105-0867

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Babe Knit High-Rise Mini Skirt

    Channel a boho babe vibe in this sweater knit mini skirt featuring a high-rise waist and a short, curve-hugging fit. Style with the matching tube top for a chic and seamless look!

    Shop Matching Top: Bohemian Babe Knit Cutout Tube Top

    Fit & Features

    • Sweater knit fabric, ribbed hems, high stretch
    • High-rise waist
    • Mini-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06501-000022

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • 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
  • 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
  • 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
  • Flirty And Flowy Striped Woven Halter Top

    She's flirty, she's flowy, she's your new fave halter top for the summer season. The lightweight striped woven fabric and open back keep it breezy, while the front flyaway design gives just the right amount of effortless edge.

    Fit & Features

    • Lightweight woven fabric, no stretch
    • Striped pattern
    • Sleeveless deep V-neckline, halter strap, elastic back
    • Open back, tie-back spaghetti straps
    • Flyaway front design
    • Mid-length flowy fit
    • Runs true to size

    Style Number/Barcode: 06003-000087

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: M, L

  • 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
  • Casual Fave Flowy V-Neck Midi Dress

    This breezy lightweight midi dress will be your new casual fave for weekend plans. Designed with a sleeveless V-neck, low back, and mid-length flowy fit, style with a layered necklace and strappy sandals.

    Fit & Features

    • Gauze woven fabric, mini-length stretchy knit lining
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, low back
    • Hidden side pockets
    • High side slit
    • Midi-length flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000185

    Category Name: Vacation Looks

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    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
  • Sun Seeker Sheer Crochet Kimono

    Layer on the cute and relaxed vibes of this sheer crochet kimono perfect for pool parties, beach days, or vacations!

    Fit & Features

    • Sheer crochet fabric
    • Slouchy long sleeves
    • Open front design
    • Relaxed silhouette

    Style Number/Barcode: 06204-2071

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS

  • 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
  • Breezy Escape High-Rise Ruffled Shorts

    Your weekend plans aren't complete without these high-rise ruffled shorts to give you a breezy, effortless style!

    Fit & Features

    • Woven fabric
    • Stretchy, smocked high-rise waistband
    • Ruffled tier design
    • Runs true to size

    Style Number/Barcode: 06303-0295

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: OFF, WHITE

    Available Size: M, L, XL

  • 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
  • Stand Out Mid-Rise Denim Hot Shorts

    Designed to stand out, these mid-rise denim hot shorts are everything for the next concert or festival! 

    Fit & Features

    • Denim fabric with color wash tint effect
    • Mid-rise waist
    • Hidden front hook-eye and zipper closure
    • Seam detailing
    • Fitted cheeky fit
    • Runs true to size

    Style Number/Barcode: 06603-0445

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: S, M, L

  • 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
  • Getaway Vibe Tropical Print Tie-Front Top

    This airy mesh top gives off getaway vibes with its trendy tropical print and effortless tie-front design. Style with denim shorts and sandals.

    Fit & Features

    • Sheer mesh fabric, high stretch
    • Tropical print
    • V-neckline
    • Tie-front design
    • Long bell sleeves
    • Cropped hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06202-000005

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

    Product Badge:
    • Sale
  • 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
  • Cozy Luxe Lurex Knit Pants

    Get cozy in the luxe lurex knit pants. With a mid-rise drawstring waist and straight-leg fit, these pants are your go-to for effortless style and comfort.

    Fit & Features

    • Lurex knit fabrication
    • Mid-rise waist
    • Drawstring waist
    • Straight-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-2556

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GOLD

    Available Size: S, M, L

    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