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.

  • Casually Cute Tie-Front Crop Top

    Get a casually cute look, perf for weekend brunch dates with your squad, in this adorable crop top. It features long fitted sleeves, a deep V neckline, a tie-front detail, and a cropped, form-hugging fit. Pair this knit top with high waist jeans and chunky sneaks.

    Fit & Features

    • Long fitted sleeves
    • Deep V neckline
    • Tie-front
    • Cropped
    • Form-fitting style
    • Lightweight knit fabric

    Style Number/Barcode: 06202-0090

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Elevated Knit Crop Top

    Effortlessly elevate your basic look with this lightweight knit crop top. It features adjustable spaghetti straps, a V neckline, a center drawstring to create a ruched look, and a cropped, form-hugging fit. Pair this top with the matching cardigan and a pair of mom jeans for a chic vibe.

    Shop Matching Cardigan: Effortlessly Elevated Knit Cardigan

    Fit & Features

    • Sleeveless bodice
    • Adjustable spaghetti straps
    • V neckline
    • Center drawstring
    • Ruched detailing
    • Cropped, form-fitting style
    • Knit fabric with moderate stretch

    Style Number/Barcode: 06001-3117

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Flutter Sleeve Crop Top

    Create a flirty impression in this crop top that brings the charm! The top features a V-neckline with a tie front bodice, short flutter sleeves, and a cropped hem. The top is composed of a gauze fabric that offers a form hugging fit with a minimal stretch. Complete look with high waist jeans. 

    Fit & Features

    • Plunging V-neckline
    • Short flutter sleeves
    • Tie front bodice 
    • Cropped hem
    • Form hugging fit
    • Minimal stretch 

    Style Number/Barcode: 06204-0649

    Category Name: Vacation Looks

    Price: $8.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Lifestyle Floral Halter Mesh Crop Top

    Let sunshine days be filled with sand and compliments when you step out in this floral halter crop top. Perfect for vacations or staycations!

    Fit & Features

    • Floral print, mesh-lined fabric
    • Halter cowl neckline, tie strap
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000061

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Vibes Ruched Floral Midi Dress

    Give your outfit major flirty vibes when you wear this adorable midi dress! It features spaghetti straps, a scoop neckline, ruched detailing, and a mid-length, curve-hugging silhouette. The brushed knit fabric showcases an all-over floral print for a beautiful look. Style this dress with a dainty layered necklace and clear heels.

    Fit & Features

    • Spaghetti straps
    • Scoop neckline
    • Ruched detailing
    • Mid-length, form-hugging fit with a moderate stretch 
    • Brushed knit fabric
    • Floral print

    Style Number/Barcode: 05101-0972

    Category Name: Vacation Looks

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling Flirty In Florals Crop Top

    Keep it flirty in a crop top that brings the charm! The crop top features a gorgeous floral print, a square neck with a tie-front accent, long sleeves with an elastic cuff, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with high waist jeans and heels. 

    Fit & Features 

    • Floral print
    • Square neck 
    • Tie-front
    • Long sleeves with elastic cuff
    • Lightweight woven fabric
    • Relaxed fit 
    • Minimal stretch 

    Style Number/Barcode: 06003-1198

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine On Rhinestone T-Strap Sandals

    Bring the shine with luxe sandals. The sandals feature a trendy square toe, a rhinestone embellished T-strap, rhinestone trim, and a flat footbed. The sandals are composed of metallic faux patent leather. Complete look with cute matching separates. 

    Fit & Features

    • T-strap
    • Square toe
    • Rhinestones
    • Metallic 
    • Faux patent leather 

    Style Number/Barcode: 07404-0671

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stay Wild Leopard Print Bikini Bottoms

    Stay wild in a bikini top that showcases your fierce vacay style. The bikini bottoms feature a mid-rise waist, a high cut, a leopard print, and a cheeky fit. Complete look with the matching bikini top and sunglasses.

    Shop Matching Bikini Top: Stay Wild Leopard Print Bikini Top

    Fit & Features

    • Mid-rise waist
    • High cut
    • Leopard print
    • Cheeky fit
    • Form hugging fit
    • Matching bikini bottoms sold separately

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0672

    Category Name: Vacation Looks

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stay Wild Leopard Print Bikini Top

    Stay wild in a bikini top that showcases your fierce vacay style. The bikini top features a plunging sweetheart neckline, padded molded cups with supportive underwire, adjustable spaghetti straps, a leopard print, and a slider hook fasten. Complete look with the matching bikini bottoms and sunglasses. 

    Shop Matching Bikini Bottoms: Stay Wild Leopard Print Bikini Bottoms

    Fit & Features

    • Plunging sleeveless sweetheart neckline
    • Padded molded cups with underwire 
    • Adjustable spaghetti straps
    • Leopard print
    • Slider hook fasten closure 
    • Form hugging fit
    • Matching bikini bottoms sold separately 

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0524

    Category Name: Vacation Looks

    Price: $11.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Staple Mid-Rise Denim Shorts

    A true forever staple, these flattering mid-rise denim shorts hug your curves and flatter with unique seam designs and the perfect length.

    Fit & Features

    • Light wash denim
    • Mid-rise waist, seam detailing
    • Form-hugging fit
    • Front button and hidden zipper closure, belt loops
    • Four-pocket styling
    • Runs true to size

    Style Number/Barcode: 06603-000009

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, DENIM

    Available Size: L

    Product Badge:
    • Sale
  • Basic Mood Mid Rise Swim Bottoms

    Keep it basic in swim bottoms that are perf for those laid back vibes! The bottoms feature a mid-rise waist, a hipster cut, and a cheeky fit. Complete your poolside look with a matching bandeau and sunglasses. 


    Fit & Features

    • Mid-rise waist
    • Hipster cut
    • Cheeky fit
    • Form hugging fit
    • Moderate stretch 

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0695

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Essential Lace Up PVC Sandals

    Lace-up in these sleek sandals that bring the style! The sandals feature a lace-up design, an almond toe, a clear PVC strap over the toe. Complete look with a crop top and cutoff shorts. 

    Fit & Features

    • Lace-up design 
    • Almond toe 
    • Clear PVC over the toe

    Style Number/Barcode: 07404-0668

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Trendsetter Slip-On Sandals

    Showcase chic trendsetter vibes in these adorable slip-on sandals! They feature an open almond toe, a criss-cross strap design, an open back, and a flat sole. Pair these sleek faux leather sandals with a flowy blouse and denim shorts for the perf spring-ready look.

    Fit & Features

    • Open almond toe
    • Criss-cross strap design
    • Open back
    • Flat sole
    • PU material

    Style Number/Barcode: 07404-0700

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Criss Cross Chic Bikini Top

    Get crossed up in this chic bikini top that was made to slay! The bikini top features a plunging sweetheart neckline, triangle cups, mini bar straps at the center of the bodice, sleek spaghetti straps, and a multi-row bar strap back. Complete your poolside look by mixing and matching with hipster swim bottoms and sunglasses. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Triangle cups
    • Mini bar straps at the center of the bodice
    • Spaghetti straps
    • Cropped hem
    • Form hugging fit, moderate stretch 

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0547

    Category Name: Vacation Looks

    Price: $4.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Mood Bandeau Swim Top

    Keep it basic ins a bandeau swim top that is perf for those laid-back vibes. The swim top features a sleeveless straight neckline and a cropped hem. Complete your poolside look with hipster cut swim bottoms and sunglasses.


    Fit & Features

    • Bandeau design
    • Straight sleeveless neckline
    • Cropped hem
    • Form-hugging fit
    • Moderate stretch

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0548

    Category Name: Vacation Looks

    Price: $5.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Velvet Chenille Scrunchie Six Pack

    Treat tresses to a cute scrunchie to create those trendy updos! The pack includes a variety of six scrunchies that are composed of a velvet chenille fabric. Nail that effortlessly put-together look with an updo and matching separates for a casual day out.

    Fit & Features

    • Six scrunchies
    • Variety of colors
    • Velvet chenille

    Style Number/Barcode: 07006-0193

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Let's Get Cheeky Wired Bikini Top

    Let's get a little cheeky this summer in a swimsuit that screams fun and flirty! The bikini top features a plunging sweetheart neckline, wired cups, adjustable spaghetti straps, and a bar hook fastening closure. Complete your vacation outfit with the matching bikini bottoms and sunglasses.

    Shop Matching Swim Bottoms: Let's Get Cheeky High Hip Bikini Bottoms

    Fit & Features

    • Wired
    • Adjustable spaghetti straps
    • Bar hook closure center back
    • Fully lined
    • Nylon
    • Moderate stretch


    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0479

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Style Three-Pack Necklace Set

    Accessorize with this gorgeous necklace set to add a chic style to your everyday look! It features three necklaces, the shortest a dainty chain with a center sleek horizontal bar charm, the middle a dainty chain with mini bar details and a center rhinestone charm, and the longest a thicker chain with a center floral engraved pendant. Pair this necklace pack with a basic bodysuit and denim for a subtle hint of glam.

    Fit & Features

    • Three necklaces
    • Bar charm
    • Rhinestone charm
    • Floral engraved pendant

    Style Number/Barcode: 07002-0595

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Latina Baseball Cap

    Oh hey, girl! Let this hat showcase your Latina pride! The hat features a traditional baseball cap design and an embroidered "Latina" script. This hat would go perf with all your casual OOTDs!

    Fit & Features

    • Traditional baseball cap design
    • Embroidered "Latina" Script

    Style Number/Barcode: 07302-0311

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Chic Cross Hoop Earrings

    Showcase a trendy chic vibe when you accessorize with these earrings! They feature a thin hoop with a drop design with a dainty cross charm. Pair these earrings with a sleek ring pack to add a glam style to your look.

    Fit & Features

    • Thin hoop
    • Drop design with a cross charm

     

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

    Style Number/Barcode: 07001-0714

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Essential Trendy Trim Square Sunglasses

    Stay on trend with these essential sunglasses that elevate your outfit! The sunnies feature a square-shaped frame, a sleek metal trim, nose pads for added comfort, and UV protective lenses. Complete look with a floral swimsuit and sandals for a cute poolside look. 

    Fit & Features

    • Square-shaped frames 
    • Sleek trim
    • Nose pads
    • 100% UV protection 

    Style Number/Barcode: 07008-0803

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Getaway Low Rise Bikini Bottoms

    Plan that dream getaway with bikini bottoms to soak up the sun in! The bottoms feature a low-rise waist, high cut, and a cheeky bottom. Complete your poolside outfit with the matching bikini top and sandals. 

    Shop Matching Bikini Top: Glam Getaway Smocked Bikini Top

    Fit & Features

    • Low-rise waist
    • High cut
    • Cheeky bottom 
    • Matching bikini top sold separately 

     

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07105-0630

    Category Name: Vacation Looks

    Price: $11.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Getaway Smocked Bikini Top

    Plan that dream getaway with a bikini top to soak up the sun in! The bikini top features a scoop neckline, a smocked bodice, and adjustable spaghetti straps. Complete your poolside outfit with the matching bikini bottoms and sandals.

    Shop Matching Bikini Bottoms: Glam Getaway Low Rise Bikini Bottoms

    Fit & Features

    • Sleeveless scoop neckline
    • Smocked bodice
    • Removable padding
    • Adjustable spaghetti straps
    • Matching bikini bottom sold separately

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    Style Number/Barcode: 07104-0482

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Booked And Busy Strapless Skort Romper

    A strapless skort romper for any of your weekend plans or vacations! With a sleek bodycon fit and a flirty skirt overlay with a slit accent, you'll win style points anywhere you go.

    Fit & Features

    • Woven fabric
    • Strapless neckline
    • Back zipper closure
    • Bodycon silhouette
    • Skirt overlay with slit accent, shorts lining
    • Romper in size small is 23" top hem to bottom hem with an 11.5" front rise and a 2" inseam
    • Runs true to size

    Style Number/Barcode: 06403-1104

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free