Vacation Looks
Vacation dressing should be easy, stylish, and ready for wherever the day takes you. Start with mini sundresses and flirty rompers that work for both sightseeing and rooftop drinks at sunset. Add in flowy maxis, crochet cover-ups for poolside sunbathing, and sleek sunnies that instantly pull a look together. From cutoff denim shorts to swimwear with eye-catching details, these outfits keep your suitcase light and your style on point for every getaway moment.
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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.
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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