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 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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Stylish Floral Flair Crop Top
You'll have that stylish floral flair in this adorable crop top that is perfect for spring! It features a sleeveless bodice with tie shoulder straps, a round neckline, hook and eye front closures, ruched detailing, and a cropped, form-hugging fit. The top is composed of a floral printed woven fabric with a woven lining and has no stretch. Complete your look with denim shorts and gold hoop earrings.
Fit & Features
- Tie shoulder straps
- Round neckline
- Hook and eye front closures
- Ruched detailing
- Cropped, form-fitting style
- Lined woven fabric with no stretch
- Floral print
Style Number/Barcode: 06003-1157
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Poised Paper Bag Ponte Shorts
Keep it poised in paper bag shorts that are totally on-trend! The shorts feature a high rise paper bag waist, a tie waist belt with belt loops, side pockets, and a wide-leg fit. The shorts are composed of a curve-hugging Ponte-knit fabric that offers a moderate stretch. Complete look with a lace crop top.
Fit & Features
- High rise paper bag waist
- Tie-waist belt with belt loops
- Side pockets
- Wide-leg fit
- Ponte-knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06503-0206
Category Name: Vacation Looks
Price: $13.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty and Fluttery Butterfly Charm Necklace
Keep it flirty with a charming butterfly necklace that showcases your sweet side. The necklace features a dainty chain link and a butterfly charm pendant composed of baguette gemstones and rhinestone stones. Complete look with a floral dress and wedges.
Fit & Features
- Dainty chain link
- Butterfly charm
- Rhinestones
- Baguette gemstones
- Adjustable lobster clasp closure
Style Number/Barcode: 07002-0665
Category Name: Vacation Looks
Price: $5.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Florals Ruffled Chiffon Mini Dress
Bring the charm in a ruffled mini dress that makes a sweet impression! The dress features a plunging V-neckline, adjustable cross-straps, a floral print, tiered ruffles, and a mini-length silhouette. The dress is composed of a sheer lined chiffon fabric that offers a form-hugging fit that offers a minimal stretch. Complete your look with wedges and a floppy hat for a brunch-worthy outfit.
Fit & Features
- Sleeveless V-neckline
- Adjustable cross-straps
- Floral print, back zipper closure
- Tiered ruffles
- Mini length silhouette
- Chiffon fabric, knit lining
- Fits true to size
Style Number/Barcode: 05101-0463
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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