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.

  • Dreamy Boho-Chic Teardrop Earrings

    Get a dreamy boho-chic look when you accessorize with these gorgeous earrings. They feature a teardrop-shaped design with a detailed textured trim with mini cutouts. Pair these earrings with a flowy lace duster and strappy sandals.

    Fit & Features

    • Teardrop-shaped design
    • Textured trim with mini cutouts
    • Fish hook closure

     

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

    Style Number/Barcode: 07001-0685

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lace N' Luxe Crochet Bralette

    Keep it luxe with a lace bralette that brings the chic to your look! The bralette features a crochet lace body, a plunging V-neckline, a double row of adjustable spaghetti straps that lead to a cross-back design, removable padded cups, a longline lace hem. Complete look with false lashes to nail that sultry look.

    Fit & Features

    • Plunging V-neckline, padded cups
    • Double row of adjustable spaghetti straps
    • Cross back 
    • Longline line hem 
    • Crochet lace 
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 07107-0539

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom With Beauty Floral Jumpsuit

    Let your beauty bloom in this adorable floral jumpsuit that is a must-have for the spring season! It features spaghetti straps that lead to a cross-back design, a V neckline, a high waist seam, and wide pant legs. Style this jumpsuit with a denim jacket and cute mules.

    Fit & Features

    • Spaghetti straps
    • Cross-back design
    • V neckline
    • High waist seam
    • Wide pant legs
    • Knit fabric with a moderate stretch
    • Floral print
    • Runs true to size

    Style Number/Barcode: 06502-0362

    Category Name: Vacation Looks

    Price: $18.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Escape Off-The-Shoulder Jumpsuit

    Feel like you're on a getaway in paradise in this adorable floral-printed jumpsuit! It features an off-the-shoulder neckline with a tiered popover detail, a high waist seam, and flowy pant legs. The knit fabric offers a moderate stretch and showcases an all-over tropical floral print, making the jumpsuit perf for warm weather. Complete your look with hoop earrings and cute wedges.

    Fit & Features

    • Off-the-shoulder neckline
    • Tiered popover detail
    • High waist seam
    • Flowy pant legs
    • Knit fabric with a moderate stretch
    • Tropical floral print
    • Runs true to size

    Style Number/Barcode: 06502-0363

    Category Name: Vacation Looks

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Eyelet Knit Tie Front Crop Top

    Keep it cute with a tie-front top that brings those cool-girl vibes. The top features a plunging tie front, long sleeves, and a cropped hem. The top is composed of a lightweight woven fabric that features an eyelet pattern. The top offers a relaxed fit with minimal stretch. Complete look with cutoff shorts. 

    Fit & Features

    • Plunging tie front
    • Long sleeves
    • Cropped hem 
    • Lightweight woven fabric
    • Eyelet pattern 
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06202-0145

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Daydream Tie-Front Romper

    You'll look like a total daydream in this trendy floral romper! It features short sleeves, a V neckline with a tie-front detail, a center waist cutout, and shorts. The lightweight woven fabric showcases an all-over floral print that will have you ready for your weekend getaway. Complete your look with earrings and wedges.

    Fit & Features

    • Short sleeves
    • V neckline with a tie-front
    • Back zipper closure
    • Center waist cutout
    • High waist seam
    • Woven fabric with no stretch
    • Floral print
    • Runs true to size

    Style Number/Barcode: 06303-0102

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Double Band Basic Nubuck Mules

    Bring it back to basics with mules that slay! The mules feature an open back design, a double row of bands, and a thin block heel. The mules are composed of a faux nubuck material. Complete look with a ribbed midi dress and moto jacket. 

    Fit & Features

    • Open back 
    • Double row of bands
    • Open almond toe
    • Thin block heel 
    • Faux nubuck material 

    Style Number/Barcode: 07401-2691

    Category Name: Vacation Looks

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Causing Trouble High Rise Cutoff Shorts

    Cause a little trouble with these edgy shorts! The shorts feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, heavy destruction throughout, and a cutoff hem. Complete look with a ruched crop top and wedges. 

    Fit & Features

    • High rise waist
    • Single-button with hidden zipper closure 
    • Traditional five-pocket with belt loop design 
    • Heavy destruction 
    • Cutoff hem
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 06603-0201

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Absolute Charm Pleated Lace Trim Mini Skirt

    Stroll like an absolute charmer in this ponte pleated mini skirt with a flirty eyelet lace trim that elevates your look!

    Fit & Features

    • Ponte knit fabric, stretchy knit shorts lining
    • High-rise waist
    • Side zipper and hook-eye closure
    • Pleated silhouette
    • Eyelet lace trim mini-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1259

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic And Chic Flowy Kimono

    Add this basic and chic flowy kimono to your wardrobe for a light layer that will give you a laidback look! It features kimono-style sleeves, an open front, and a flowy silhouette. The lightweight woven fabric has no stretch. Wear this kimono as a cover-up over your fave swimwear for the perfect poolside outfit.

    Fit & Features

    • Kimono-style sleeves
    • Open front
    • Flowy silhouette
    • Semi-sheer polyester fabric
    • No stretch

    Style Number/Barcode: 06204-0914

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek and Sultry Caged One Piece Swimsuit

    Keep it sultry with a sexy one-piece swimsuit that shows off more than a hint of skin. The swimsuit features a plunging V-neckline with a caged design, tank straps, and a matching plunging back with a cheeky fit. Complete look with sunnies and a floppy hat for a beachside look.

    Fit & Features

    • Sleeveless plunging V-neckline
    • Caged design 
    • Tank-straps
    • Plunging open back 
    • High rise cut with cheeky fit bottom 


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

    Style Number/Barcode: 07109-0186

    Category Name: Vacation Looks

    Price: $4.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Vibes Ruffle Detail Romper

    Bring those flirty vibes to your summer style with this absolutely adorable romper! It features short flutter sleeves, a V-neckline with a wrap-front design, a tie-front belt with tassel details, a faux wrap-front, fitted shorts, and ruffle accents. Complete your look with sleek earrings and cute wedges.

    Fit & Features

    • Short flutter sleeves
    • V-neckline, wrap-front design
    • Back zipper and hook and eye closure
    • Tie-front belt with tassel details
    • Faux wrap-front covering fitted shorts
    • Ruffle accents
    • Woven fabric with a lining and no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0081

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Bound Rose Print Swim Top

    Pack this adorable rose printed swim top for your next getaway! It features ruffle shoulder straps, a sweetheart neckline with a ruffle trim, wired cups, a tie-front detail, and a slide hook back closure. Complete your look with the matching swim bottoms and a pair of strappy sandals.

    Shop Matching Bottoms: Vacay Bound Rose Print Swim Bottoms

    Fit & Features

    • Ruffle shoulder straps
    • Sweetheart neckline with a ruffle trim
    • Wired cups
    • Tie-front
    • Removable padding
    • Slide hook back closure
    • Rose print
    • Runs true to size

     

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

    Style Number/Barcode: 07104-0552

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Bound Rose Print Swim Bottoms

    Pack these adorable rose printed swim bottoms for your next getaway! They feature a top ruffle trim, side tie closures, and a cheeky bottom. Complete your look with the matching swim top and pair of strappy sandals.

    Shop Matching Top: Vacay Bound Rose Print Swim Top

    Fit & Features

    • Top ruffle trim
    • Side tie closures
    • Cheeky bottom
    • Rose print
    • Runs true to size

     

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

    Style Number/Barcode: 07105-0699

    Category Name: Vacation Looks

    Price: $3.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Vibes Smocked Tank Top

    Keep it basic and chic with this cute tank! The tank top features a square neckline, a smocked bodice, spaghetti straps, and a cropped hem. The tank top is composed of a stretchy smocked knit fabric that offers a moderate stretch. Complete look with cutoff shorts.

    Fit & Features

    • Sleeveless square neckline
    • Smocked bodice
    • Spaghetti straps
    • Cropped hem
    • Smocked knit fabric 
    • Relaxed fit
    • Moderate stretch 

    Style Number/Barcode: 06001-3158

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Glam Four-Pack Necklace Set

    Get that effortlessly glam look you've been wanting with this trendy necklace set. It features four necklaces, the first shortest layer a flat snake chain, the second layer a dainty flat chain, the third layer a dainty chain with a center detailed metal coin, and the longest layer a dainty textured chain with a center textured metal coin. Pair this set with a basic tee to elevate the look.

    Fit & Features

    • Four-pack necklace set
    • Various styled chains
    • Two center metal coin charms

    Style Number/Barcode: 07002-0673

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love At First Bloom Ditsy Floral Mini Dress

    Fall headfirst for this floral dress that showcases your sweet side. It features adjustable spaghetti straps, a ruffled sweetheart neckline with a center cutout and tie-front, a stretchy smocked back, and a short, curve-hugging fit. Complete your look with strappy sandals and a cute handbag.

    Fit & Features

    • Adjustable spaghetti straps
    • Ruffled sweetheart neckline
    • Center cutout and tie-front
    • Stretchy smocked back
    • Mini-length, form-hugging fit
    • Sheer chiffon fabric with a ditsy floral print, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-0756

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Sweetheart Floral High Slit Maxi Dress

    Show off your sweet side with a floral dress that brings the romance! The dress features a sleeveless V-neckline, spaghetti straps, a floral print, and a maxi length silhouette accented with a high side slit. The dress is composed of a smooth knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Floral print
    • Maxi length silhouette
    • High side slit
    • Smooth knit fabric 
    • Relaxed fit, moderate stretch 

    Style Number/Barcode: 05102-0773

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy And Stylish Stiletto Mules

    Give your look a sassy style with these on-trend heeled mules! They feature an open square toe, a toe strap with a woven design, an open back, and a short stiletto heel. Pair these mules with mom jeans and a floral blouse.

    Fit & Features

    • Open square toe
    • Toe strap with a woven design
    • Open back
    • Short stiletto heel
    • PU material
    • Runs true to size

    Style Number/Barcode: 07401-2723

    Category Name: Vacation Looks

    Price: $15.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetting Queen Heeled Mules

    Yes babe, reign in your status as a trendsetting queen in these adorable mules! They feature an open almond toe, a toe strap with a quilted design, an open back, and a low block heel. Complete your look with a chic crop top and a denim mini skirt.

    Fit & Features

    • Open almond toe
    • Toe strap with a quilted design
    • Open back
    • Low block heel
    • PU material
    • Runs true to size

    Style Number/Barcode: 07401-2724

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Strappy One-Piece Swimsuit

    Give your poolside look a chic vibe in this trendy one-piece swimsuit! It features adjustable spaghetti straps, a padded deep V neckline with bar front details, a low scoop back, cut-outs on each side with bar strap details, and a high cut semi-cheeky fit. Pair this swimsuit with a sheer mesh flowy duster and a cute boater hat.

    Fit & Features

    • Adjustable spaghetti straps
    • Padded deep V neckline
    • Bar front details
    • Low scoop back
    • Side cut-outs with bar strap details
    • High cut semi-cheeky fit

     

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

    Style Number/Barcode: 07109-0254

    Category Name: Vacation Looks

    Price: $18.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Vibes Tank Swim Top

    Give off those effortless and chic beachy vibes in this swim top! It features a tank design with a straight-across neckline, a center top slit, adjustable and removable spaghetti straps, and a tie-back closure. Complete your look with the matching swim bottoms and some cool aviator sunglasses.

    Shop Matching Bottoms: Beachy Vibes Hipster Swim Bottoms

    Fit & Features

    • Tank design
    • Straight-across neckline
    • Top slit detail
    • Adjustable and removable spaghetti straps
    • Tie-back closure
    • Textured fabric
    • Runs true to size


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

    Style Number/Barcode: 07104-0501

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Stud Strappy Jelly Sandals

    Put an edgy-cute foot forward in these jelly sandals with dual straps and studded accents that elevate your everyday look.

    Fit & Features

    • Round toe
    • Dual straps with studded accents
    • Flat sole
    • Jelly material
    • Runs true to size

    Style Number/Barcode: 07404-1260

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK, GOLD

    Available Size: 7, 8, 9, 5

    Product Badge:
    • Sale
  • High Rise Frayed Cutoff Shorts

    Give your shorts an edgy twist with deets that stand out. The denim shorts feature a high-rise waist, a single button with hidden zipper closure, a traditional five-pocket with belt loop design, and a frayed cutoff hem. Complete the look with a ruched crop top. 

    Fit & Features

    • High rise waist
    • Single-button with hidden zipper closure
    • Traditional five-pocket with belt loop design 
    • Frayed cutoff hem
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06603-0175

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale