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.

  • Polished Strut Faux Pearl Straw Stiletto Pumps

    Indulge in the ultimate polished pumps for a poised summer style! These closed pointed toe pumps feature a stunning faux pearl accent that adds a touch of chic to any outfit, while the stiletto heel elevates the look.

    Fit & Features

    • Stiletto heel
    • Closed pointed-toe, faux pearl accent
    • Adjustable ankle strap with buckle closure
    • Straw material
    • Runs true to size

    Style Number/Barcode: 07401-000080

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: IVORY

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

  • Flirty Moves Ruffled Slit Knit Midi Skirt

    Make major flirty moves and create an enticing aura in this ruffled slit midi skirt! Designed with a stretchy smooth knit fabric, it features a high-rise elasticized waist for comfortable wear, ruching down the side seam to accentuate your curves, a sultry high-cut side slit with a ruffled hem, and a bodycon fit along the midi-length silhouette. Style with the matching crop top for a girl's night out!

    Shop Matching Top: Flirty Moves Ruffled Tie-Front Knit Crop Top

    Fit & Features

    • Stretchy smooth knit fabric
    • High-rise elasticized waist
    • Ruched side seam
    • High side slit, ruffled hem
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1042

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Glowing Rhinestone Strap Sandals

    Always glow in these rhinestone strap sandals to dress up your everyday look or date night dress!

    Fit & Features

    • Square toe
    • Asymmetrical rhinestone straps
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1257

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sun Rays Tropical V-Neck Babydoll Mini Dress

    Flaunt beachy perfection in this tropical babydoll dress with a strappy tie-back that turns heads with every wear! Style with sandals for a cute vacation look.

    Fit & Features

    • Tropical print, woven fabric, bust knit lining
    • V-neckline, twisted bust
    • Spaghetti straps
    • Strappy tie-back design
    • Babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000042

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: In Stock

    Available Color: OLIVE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Bring The Drama Bell Sleeve Tie Front Crop Top

    Bring the drama this season in this crop top with a flirty tie-front and statement bell long sleeves to elevate your favorite bottoms!

    Fit & Features

    • Woven linen-blend fabric
    • Bell long sleeves
    • Tie-front design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-2100

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: M, L

    Product Badge:
    • Best Seller
  • Looking Good V-Waist Smocked Flare Pants

    Looking good will be effortless in these flare pants perfect for vacation or a hot night out! Made of smocked stretchy knit fabric, these pants offer comfort and a flattering silhouette. The cinched mid-rise V-waist and hip-hugging fit will accentuate your curves, while the flared hem adds a touch of flare to your outfit. Complete the look with the matching top.

    Shop Matching Top: Looking Good Sweetheart Tie Front Crop Top

    Fit & Features

    • Stretchy smocked knit fabric
    • Mid-rise V-waist with cinch
    • Hip-hugging fit
    • Flare hem
    • Runs true to size

    Style Number/Barcode: 06502-2495

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On The Beach Three-Pack Anklet Set

    Take a stylish stroll along the sandy beach wearing this three-pack anklet set. It features two dainty chain link anklets and one chain anklet with a seashell charm. Each has a lobster clasp closure. Complete the look in cute sandals.

    Fit & Features

    • Three-pack anklet set
    • Two dainty chain link anklets
    • One chain anklet with seashell charm
    • Each has a lobster clasp closure

    Style Number/Barcode: 07003-0554

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Plans Mid-Rise Linen Shorts

    Cute for casual plans, these mid-rise linen blend shorts offer a breezy style to your look! Shop the matching top.

    Fit & Features

    • Woven linen-blend fabric
    • Elasticized mid-rise waist
    • Flowy dolphin trim hem
    • Runs true to size

     

    Shop The Matching Top: Casual Plans Button-Down Linen Top

    Style Number/Barcode: 06303-000001

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: OFF, WHITE

    Available Size: XS, M, L

    Product Badge:
    • Part of a Set
  • Sweet Existence High-Rise Bow Mini Ruffle Skort

    Step out wearing this pointelle mini skort for a sweet look on any sunny day! Features a high-rise waist with delicate lace trim and a charming bow, creating a flattering and feminine silhouette. The bodycon fit hugs your curves while the layered ruffled mini-length hem adds a playful touch. Complete the look in a flirty crop top and sneakers for casual plans!

    Fit & Features

    • Pointelle knit fabric, shorts lining
    • High-rise waist, lace trim and bow
    • Bodycon fit
    • Layered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1197

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Sweet Floral Strapless Mini Dress

    This sassy sweet strapless mini dress was made for a vacay or weekend getaway! Designed with an abstract floral print, it features side ruching leading to a chic short slit and a flowy A-line silhouette.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Abstract floral print
    • Strapless straight neckline
    • Side ruching, adjustable tie, short side slit
    • Mini-length A-line silhouette, asymmetric hem
    • Runs true to size

    Style Number/Barcode: 05103-000094

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S

    Product Badge:
    • Sale
  • Perfect In Paradise Floral One-Piece Swimsuit

    Create a poolside look perfect for paradise in this one-piece swimsuit featuring a large floral print, a halter neckline with an alluring bust cutout, and a cheeky fit. Style with gold bangle bracelets and flat sandals.

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Large floral print
    • Halter neckline, large bust cutout
    • Tie-back halter straps, open lower back
    • Cheeky fit
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000013

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • New Favorite Thong Strap Low-Block Heels

    These simple yet stylish low-block heels will become your new fave go-to! Made with sleek faux leather material, they feature an open square-shaped toe with a thin thong strap design, thin adjustable ankle and heel straps for a customized fit, and a low block heel for comfort and a chic look. Pair with a mini handbag for your weekend plans!

    Fit & Features

    • 3" Low block heel
    • Faux leather upper
    • Square toe
    • Thong strap design
    • Adjustable ankle and heel straps, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4664

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Personality Button Up Crop Linen Shacket

    An easygoing babe like you will appreciate this linen shacket for effortless styling! Featuring three quarter roll cuffed sleeves, a collar neckline, and button-up front closure, this shacket brings versatility to your wardrobe. With flap pockets and a cropped hem, this shacket adds a playful touch to any outfit. Complete the look in trendy boots.

    Fit & Features

    • Linen blend woven fabric, no stretch
    • Collar neckline
    • Button up front closures
    • Flap pockets
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1784

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Sun Floral Tie-Front Bikini Top

    Enjoy the sweet sunshine at the pool or beach in this floral tie-front bikini top! Pair with the matching bikini bottoms.

    Fit & Features

    • Floral print, knit lined fabric
    • Short puff sleeves
    • Tie-front design
    • Ruffled trim
    • Runs true to size

     

    Shop The Matching Bikini Bottoms: Sweet Sun Floral Bikini Bottoms

    Style Number/Barcode: 07104-0726

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Fit High-Rise Distressed Denim Shorts

    You'll love the classic fit of these high-rise distressed denim shorts, a summertime essential! Perfect for pairing with a crop top and sandals.

    Fit & Features

    • Cotton denim fabric, no stretch
    • High-rise waist
    • Five-pocket and belt loop design
    • Hidden front zipper and button closure
    • Distressed detailing, frayed hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06603-0454

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: S, M, L, XL

  • Step Into Summer Linen Wooden Platform Heels

    Step into summer looking fabulous in these platform heels! These block heels feature a square toe with a wide strap, an adjustable ankle strap with buckle closure, and a lightweight wooden platform sole for a trendy finish. Complete the look with a cute handbag.

    Fit & Features

    • 3.5" Block Heel
    • Square toe
    • Adjustable ankle strap, buckle closure
    • Lightweight wooden platform sole
    • Luxe fit cushioned insole
    • Linen material
    • Runs true to size

    Style Number/Barcode: 07401-4886

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Statement Flower Earrings

    Add whimsical flair with these flower earrings, perfect for special occasions to date nights! 

    Fit & Features

    • Flower decorations
    • Fish hook

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000013

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: NS

  • Destined For Sun Tropical Mesh Tie Front Top

    This tropical sheer mesh top is destined to go with you on the next sunny getaway! Featuring long sleeves with cuffs, a tie-front design, and a cropped hem to highlight your curves. Complete the look with the matching bottoms.

    Shop The Matching Bottoms: Destined For Sun Tropical Mesh Mini Skirt

    Fit & Features

    • Tropical palm print, sheer mesh fabric, moderate stretch
    • Long sleeves with cuffs
    • Tie-front design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-0452

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mornings In Tulum Tropical Tie-Front Crop Top

    Waking up in paradise got sweeter with this tropical crop top in your luggage! It boasts flowy short sleeves and a tie-front design perfect for styling over a bikini. Pair with the matching pants.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Short sleeves
    • Tie-front design
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Pants: Mornings In Tulum Tropical Wide-Leg Pants

    Style Number/Barcode: 06202-000015

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Cute Trek Strappy Lace-Up Flat Sandals

    Your trek to the farmer's market is looking cute in these statement flat sandals! They feature a square toe, a caged strappy design with knotted accents, and a trendy lace-up ankle that lets you customize the style on faux leather material. Complete the look with a trendy handbag.

    Fit & Features

    • Flat sole
    • Square toe
    • Strappy caged design with knotted accents
    • Lace-up ankle
    • Lightly cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1155

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make A Statement Strappy Open Back Jumpsuit

    Make a statement in this head turning jumpsuit featuring a flattering cowl neckline and show-stopping beaded back detail with strappy open design and a straight leg silhouette creates a sleek, elongated look.

    Fit & Features

    • Texture knit fabric, partial knit lining
    • Cowl neckline, bungee spaghetti straps
    • Strappy beaded open back
    • Straight-leg fit
    • Runs true to size

    Style Number/Barcode: 06502-000023

    Category Name: Vacation Looks

    Price: $64.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Gorgeous Allure Chiffon Palazzo Pants

    Radiate your gorgeous allure in these chic chiffon palazzo pants! Designed with an airy sheer chiffon fabric with a lightweight woven lining for coverage, these pants are perfect for the summer season. They feature a high-rise fit with a stretchy elastic waistband and a relaxed wide-leg silhouette for style and comfort. Complete the look with the matching bra top!

    Shop Matching Top: Gorgeous Allure Ruched Chiffon Bra Top

    Fit & Features

    • Sheer chiffon fabric, woven lining, no stretch
    • High waist, elastic waistband
    • Wide-leg fit
    • Runs true to size

    Style Number/Barcode: 06402-1413

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • First Day Of Spring Puff Sleeve Smocked Romper

    Embrace the beauty of spring in this adorable romper! Featuring delicate puff short sleeves and a tie-front bust, this romper flatters everyone. The stretchy smocked waist and flowy short-length hem provide ultimate comfort and style. Complete the look in cute sandals and sunnies for any casual outing!

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Tie-front bust
    • Stretchy smocked waist
    • Runs true to size

    Style Number/Barcode: 06303-0265

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • One Take V-Neck Ruffle Skater Romper

    One take in this skater romper and you'll be so obsessed! With a flirty tie back design and flattering skater silhouette, this romper will be your favorite style for brunch to parties!

    Fit & Features

    • Knit fabric, moderate stretch
    • Adjustable spaghetti straps
    • Ruffle V-neckline
    • Tie-back design
    • Skater silhouette
    • Ruffle layered short-length hem
    • Runs true to size

    Style Number/Barcode: 06503-1142

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK, PINK, IVORY

    Available Size: XS, S, M, L