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.

  • Stacked On Basics Wide Fit Mules

    Stack on the style with cute mules that nail your everyday looks! The mules feature a comfortable wide-fit sole, an open back, an open square toe, a double-row strap design, and a low block heel. The mules are composed of a faux leather material. Complete look with a puff sleeve top and jeans! 

    Fit & Features

    • Open back 
    • Open square toe
    • Double-row strap design 
    • Low block heel
    • Faux leather material 
    • Wide fit sole
    • Runs true to size

    Style Number/Barcode: 07401-3543

    Category Name: Vacation Looks

    Price: $7.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Knit List Jelly Sole Sneakers

    Kick back and keep it comfy in this pair of knit sneakers! Designed with a knit body, jelly sole and lace-up vamp. Pair with leggings for the ultimate off-duty vibes. 

    Fit & Features

    • Lace-up vamp
    • Jelly sole
    • Knit body 
    • Almond toe

    Style Number/Barcode: 07407-0209

    Category Name: Vacation Looks

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunshine Chic Straw Block Heels

    Work it on your next stroll in the park in this pair of block heels! They're designed with oh-so-chic straw accents, a block heel, and an ankle strap. Wear them with a sundress for the sweetest sunshine style.

    Fit & Features

    • Straw detailing
    • Block heel
    • Ankle strap
    • Open almond toe 

    Style Number/Barcode: 07401-3467

    Category Name: Vacation Looks

    Price: $7.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Start A Spark Ruched Mini Dress

    Start a spark with a mini dress that showcases your luxe style! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with lucite heels and gold jewelry. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched body
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4191

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Stylish Affair Ruffled Midi Dress

    Make a dramatic entrance with a midi dress that is perfect for your cocktail event. The dress features a ruffled off-the-shoulder neckline a bodycon fit, and a midi length silhouette with a ruffled hem. The dress is composed of a crepe fabric that offers a form hugging fit with a moderate stretch. Complete look with stiletto heels and statement earrings.

    Fit & Features

    • Ruffled off the shoulder neckline
    • Bodycon fit
    • Midi length silhouette 
    • Ruffled hem 
    • Crepe fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-0989

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Moment Floral Chiffon Skater Dress

    Have a flirty moment in this adorable floral chiffon skater dress! It features a sleeveless V-neckline with a wrap-front design, thin shoulder straps that lead to a front ruffle overlay, and an open-back design with a tie-back detail. The dress has a high waist with a tie-front accent and a short, skater silhouette with a tiered hem. Style this dress with hoop earrings and mules.

    Fit & Features

    • Sleeveless V-neckline, wrap-front design
    • Thin shoulder straps, front ruffle overlay
    • Open back, tie back detail, lower back zipper and hook and eye closure
    • High waist, tie-front
    • Mini-length skater silhouette, tiered hem
    • Floral print, sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1142

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Making My Mark Ribbed Mini Dress

    Make your style mark with a mini dress that is part casual, part glam! The dress features a sleeveless crew neckline, tank shoulder straps, and an open back with criss-cross straps. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Open back, criss-cross straps
    • Lined ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4270

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Living In Luxe Quilted Jelly Matte Purse

    Live it up in luxe with a purse that elevates your outfit. The bag features a quilted matte jelly body, a small rectangular body, a fold-over closure with turn-lock fasten, and a dainty chain-link shoulder strap. Complete the look with a floral blouse and skinny jeans.

    Fit & Features

    • Small rectangular body
    • Quilted diamond design
    • Jelly matte body
    • Fold-over closure with turn-lock fasten
    • Chain link shoulder strap

    Style Number/Barcode: 07203-0663

    Category Name: Vacation Looks

    Price: $8.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Sunny Strapless Ruffle Eyelet Mini Dress

    This eyelet mini dress is perfect for any sunny day and will be a favorite for shower celebrations, brunch, or graduations! The dress boasts a stretchy smocked bodice that hugs your figure while the ruffled mini-length hem adds a flirty allure.

    Fit & Features

    • Eyelet woven-lined fabric
    • Strapless neckline
    • Stretchy smocked bodice
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4019

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Girl Metallic Toe Strap Sandal

    Keep the glam vibes going in this pair of metallic sandals. They feature a rhinestone embellished clear strap and toe strap. Pair with a velvet dress for a showstopping statement. 

    Fit & Features 

    • Slip-on design
    • Embellished clear strap
    • Toe strap
    • Faux leather material
    • Runs true to size 

    Style Number/Barcode: 07404-0932

    Category Name: Vacation Looks

    Price: $7.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Studded Chic Faux Leather Espadrille Sandals

    Keep it chic with studded sandals that are part edgy and part casual. The sandals feature an adjustable ankle strap, an open almond toe, a multi-strap design, pyramid-shaped studs throughout, and an espadrille sole. Complete look with a romper and hoops. 

    Fit & Features

    • Adjustable ankle strap
    • Open almond toe 
    • Multi-strap design 
    • Pyramid-shaped studs
    • Espadrille sole
    • Faux leather
    • Runs true to sole

    Style Number/Barcode: 07404-0842

    Category Name: Vacation Looks

    Price: $7.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hit The Tropics Mesh Swim Wrap

    Channel a tropical vibe with a swim wrap to accent your swimsuit! The swim wrap features a tropical palm leaf print and is composed of a mesh fabric. Complete look with sandals and sunnies!

    Fit & Features

    • Tropical palm leaf print
    • Sheer mesh fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 07305-0317

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist Of Fate Wrap Midi Dress

    Wrap yourself in a midi dress that keeps it casually chic! The dress features a V-neckline, short kimono sleeves, a high center slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules and hoops. 

    Fit & Features

    • V-neckline
    • Short kimono sleeves
    • High center slit 
    • Midi length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0990

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Instincts Snake Mini Dress

    Tap into your stylish instincts with a mini dress that shows off your fierce side! The dress features a snake print, a sleeveless V-neckline, adjustable spaghetti straps, a twisted knot accent at the bodice, and a wrap silhouette with a high slit. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Snake print
    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Twisted knot accent at bodice
    • Wrap silhouette, high slit
    • Brushed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05103-3834

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Trendsetter Lace Up Midi Dress

    Stun like the true trendsetter you are with a midi dress that slays! The dress features a halter neckline with a racer bust, spaghetti straps, sexy cutouts at the waist, a lace-up back, and a midi-length silhouette. The dress is composed of a buttery lined knit fabric that offers a form hugging fit with a moderate stretch.  Complete look with mules

    Fit & Features

    • Halter neckline, racer bust
    • Spaghetti straps
    • Lace-up straps at the back
    • Cutouts at the waist
    • Midi length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-1096

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vibes Panama Hat

    This chic Panama hat is a must-have for all your weekend festivities. It features a wide flat brim and a thin ribbon band with a tie detail. Complete your look with sunglasses and a cute crossbody purse.

    Fit & Features

    • Wide flat brim
    • Thin ribbon band, tie detail
    • Faux wool material

    Style Number/Barcode: 07302-0387

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Trendsetter Panama Hat

    Showcase your status as a chic trendsetter with this stylish Panama hat. It features a wide flat brim and a thin faux leather band with a sleek flat buckle detail. Wear this hat with a faux leather jacket.

    Fit & Features

    • Wide flat brim
    • Thin faux leather band
    • Flat buckle detail
    • Faux wool material

    Style Number/Barcode: 07302-0382

    Category Name: Vacation Looks

    Price: $7.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Trendsetter Ruched Knit Mini Dress

    Showcase casual trendsetting looks in this stylish knit mini dress. It features a square neckline, short sleeves, ruched side detailing with drawstrings, and a short, form-hugging silhouette. Pair this dress with a denim jacket and cute mules for an effortless everyday outfit.

    Fit & Features

    • Square neckline
    • Short sleeves
    • Ruched side detailing
    • Adjustable drawstrings
    • Mini-length, form-hugging fit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4333

    Category Name: Vacation Looks

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Nicole High-Slit Floral Formal Dress

    Special Occasion

    You'll look oh-so-gorgeous in the flirty floral Nicole formal dress! She features a sleeveless square neckline, spaghetti straps that lead to a cross-back design, a flattering high waist seam, and a floor-length, fitted silhouette with a thigh-high front slit accented with ruffle detailing. Complete the outfit with basic block heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, cross-back design
    • High waist seam
    • High front slit, ruffle trim
    • Floor-length, fitted A-line silhouette
    • Floral print
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05002-1368

    Category Name: Vacation Looks

    Price: $14.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Casual Button-Down Mini Dress

    This cute and casual ribbed knit mini dress is the perf option for a chill everyday look! It features a sleeveless V-neckline, adjustable spaghetti straps, a faux button-down front, and a short, curve-hugging silhouette. Style this dress with sneakers.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Faux button-down front
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-0978

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Fab Snake Print Block Heels

    You'll look so fab in these trendy multi-colored snake print block heels! They feature an open square toe, a criss-cross toe strap design, an adjustable ankle strap, and a thin block heel. Style these shoes with a casual dress and a chic shoulder bag.

    Fit & Features

    • Open square toe
    • Criss-cross toe strap design
    • Adjustable ankle strap, buckle detail
    • Thin block heel
    • Multi-colored snake print design
    • Runs true to size

    Style Number/Barcode: 07401-3354

    Category Name: Vacation Looks

    Price: $7.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Dream Asymmetrical Maxi Dress

    Live out a tropical dream with a maxi dress that will have you totally vacay ready! The dress features a tropical floral print, a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, ruching at the side, and a maxi length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals

    Fit & Features

    • Tropical floral print
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross at back
    • Ruching 
    • Maxi length silhouette
    • Smooth knit fabric, form-hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05101-1200

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk Tall Clear Strap Platform Block Heels

    Legs for days and an attitude to match. These clear strap platform mules bring sky-high vibes with a chunky block heel that’s lightweight but never low-key.

    Fit & Features

    • 5" Thick block heel
    • Platform sole, lightweight wood material
    • Open square-shaped toe
    • Dual clear PVC straps
    • Open back, on-and-off styling
    • Faux leather cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000260

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Endless Summer Halter Cutout Dress

    Embrace the summer vibes in this chic curve-hugging dress! It features a sleeveless halter neckline, an open back, a center knot detail with dual waist cutouts, and an ankle-length, form-fitting silhouette. Style this dress with sleek hoop earrings.

    Fit & Features

    • Sleeveless halter neckline
    • Open back
    • Center knot detail
    • Dual waist cutouts
    • Long, form-hugging fit
    • Ribbed sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1216

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free