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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Total Keep Crepe Tie-Front Top
Dress up your outfit by layering on this crepe top featuring short sleeves and a tie-front closure along the cropped hem. Style with a basic cami and jeans.
Fit & Features
- Short sleeves
- Tie-front closure
- Cropped hem
- Crepe fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1386
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Getaway Sheer Mesh Duster
Layer on this airy sheer mesh duster to look like you're ready for an island getaway! It features long fitted sleeves, an open front, a long, flowy silhouette, and an all-over palm leaf print. Style over your fave bikini as a chic cover-up.
Fit & Features
- Long fitted sleeves
- Open front
- Long flowy silhouette, relaxed fit
- Palm leaf print
- Sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0302
Category Name: Vacation Looks
Price: $11.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Striped Pleat Shorts
Refresh your closet for summer! Show off your flirty style in these striped shorts featuring a high-rise waist, form-fitting silhouette, and pleated lined fabric. Complete the look in the matching top.
Shop Matching Top: Seasonal Striped Pleat Tank Top
Fit & Features
- High-rise waist
- Form-fitting
- Striped pattern
- Pleated lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06503-0700
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Seasonal Striped Pleat Tank Top
Refresh your closet for summer! Show off your flirty style in this striped tank top featuring a sleeveless, sweetheart neckline, adjustable spaghetti straps, and a front twist accent on the cropped hem. Complete the look in the matching shorts.
Shop Matching Shorts: Seasonal Striped Pleat Shorts
Fit & Features
- Sleeveless, sweetheart neckline, adjustable spaghetti straps
- Front twist accent
- Cropped hem
- Striped pattern
- Pleated lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06001-3987
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Beauty Tropical Print Halter Top
Show off your beauty on your next vacay in this sleek knit halter top with a trendy O-ring bust accent and an alluring tropical palm leaf print.
Fit & Features
- Smooth knit fabric, high stretch
- Tropical palm leaf print
- Sleeveless V-neckline, bust O-ring accent
- Halter strap
- Partially open back
- Fitted mid-length hem
- Runs true to size
Style Number/Barcode: 06001-000089
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Stroll Woven Slide Sandals
Take the perfect summertime stroll in these chic woven slides! The sandals feature a rounded toe, a wide toe strap, a flat sole, and a woven raffia material. Style with a sleek pair of sunglasses.
Fit & Features
- Rounded toe
- Wide toe strap
- Flat sole
- Woven raffia material
- Runs true to size
Style Number/Barcode: 07404-0980
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Mood Ombre Aviator Sunglasses
Showcase major trendy vibes in these sleek aviator sunglasses! They feature a thin metal frame with mirrored ombre lenses. Style with a mini dress and boots for the cutest summer 'fit!
Fit & Features
- Aviator design
- Thin metal frame
- Mirrored ombre lenses
- Rubber nose supports
- UV 400 protection
Style Number/Barcode: 07008-0973
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Give Me Glam Oversized Sunglasses
You're all about that glam life. These oversized shades are a must-have for you! The sunglasses feature square-shaped tinted lenses, a plastic frame, metal side trims, and thin metal arms. Style with a chic crossbody purse.
Fit & Features
- Oversized design
- Square-shaped tinted lenses
- Plastic frame
- Metal side trims
- Thin metal arms
- 100% UV protection
Style Number/Barcode: 07008-0976
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Festive Babe Crochet Fringe Top
Get ready for festival season babe! This boho crochet fringe top features a sleeveless, halter neck with tie closure, open-back, and a cropped length. Complete the look in distressed denim shorts and a ring set.
Fit & Features
- Sleeveless, halter neck with tie closure
- Open-back
- Cropped length
- Crochet design with fringe
- No stretch
- Fits true to size
Style Number/Barcode: 06005-1307
Category Name: Vacation Looks
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dance All Day Crochet Halter Top
Get ready to dance at every festival looking so fire in this crochet halter top featuring a trendy open-back with tie closure and a v-neck atop an ultra cropped hem. Complete the look in boho-flared pants.
Fit & Features
- Sleeveless, halter v-neck, tie closure
- Open-back
- Crochet design, unlined
- Fits true to size, no stretch
Style Number/Barcode: 06005-1401
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Everyday Trendsetter Cutout Crop Top
Showcase major trendsetter status in this chic crop top that is perf for every day. It features a sleeveless racer neckline, an asymmetrical cutout above the bust, and a cropped, form-hugging fit. Style with a mini skirt and mules.
Fit & Features
- Sleeveless racer neckline
- Asymmetrical cutout above the bust
- Cropped, form-hugging fit
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4206
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Hit Wonder Surplice Tie Jumpsuit
This sleeveless jumpsuit will be a hit everywhere you go! It features a collared v-neck, adjustable spaghetti straps, a surplice bodice, and a tie-waist on a straight-leg silhouette. Composed of woven fabric with a minimal stretch. Finish the look in lattice booties.
Fit & Features
- Sleeveless, collared v-neck, adjustable spaghetti straps
- Back zipper closure
- Surplice bodice
- Tie-waist, straight-leg design
- Woven fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06402-0402
Category Name: Vacation Looks
Price: $6.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Skip A Beat Criss Cross Halter Top
Your heart will skip a beat for this halter top! Featuring a sleeveless, criss-cross strap bodice with a keyhole accent, fitted crop hem, and an open-back design on stretchy rib-knit fabric. Complete the look in boyfriend jeans.
Fit & Features
- Sleeveless, halter neckline
- Criss-cross straps
- Keyhole accent
- Fitted crop hem
- Open-back design
- Stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 06001-4208
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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May Blooms Lace-Up Midi Dress
May flowers are blooming on this sultry midi dress featuring a sleeveless, cowl neck, spaghetti straps that lace up on the open back, a form-hugging fit, and a side slit accent. Complete the look in simple block heels for a daytime event.
Fit & Features
- Sleeveless, cowl neck, spaghetti straps
- Open-back, lace-up design
- Form-hugging fit
- Side slit accent
- Midi-length hem
- Slinky knit fabric, moderate stretch. fits true to size
Style Number/Barcode: 05101-1625
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Remy High Rise Fray Denim Shorts By Windsor Denim
Don't get stressed cause you'll be well dressed in the Remy high-rise denim shorts by Windsor Denim! Your curves will be blessed in these jean shorts featuring a flattering, high-rise waist, distressed accents, figure-flattering design, and a frayed cutoff hem on a medium wash denim fabric with a vintage-inspired color fade effect. Complete the look in a cute crochet crop top for a music concert.
Fit & Features
- High-rise waist
- Distressed accents, frayed cutoff hem
- Figure-flattering design
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim, color fade effect, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0240
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Good Times Flow Tulip Pants
Make many memories in these tulip pants featuring a high-rise elasticized waist, front partial slits that run from top to bottom, and a flowy wide-leg silhouette on woven fabric. Complete the look in a boho crop top and sandals for a trendy summer night dinner.
Fit & Features
- High-rise elasticized waist
- Front partial slits that run top to bottom
- Flowy wide-leg silhouette
- Back zipper closure
- Woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0659
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Palms Strapless Jumpsuit
The palms on this breezy jumpsuit are a total summer vibe! It features a strapless, sweetheart neck, a knot accented bust, elasticized lattice straps on the open back, a cutout bodice, and a wide-leg silhouette. Complete the look in sandals for a vacation fit.
Fit & Features
- Strapless, sweetheart neck
- Elasticized lattice straps on the open back
- Knot accented bust, cutout bodice
- Wide-leg silhouette
- Palm print, gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0618
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paper Bag Of Tricks Denim Cuff Shorts
These denim shorts are such a treat with no tricks! They feature a cute, paper bag high-rise waist, roll cuffed hem, dual button front, hidden zipper closure, belt loop accents, and a classic 5-pocket design. Complete the look in a bodysuit and sandals.
Fit & Features
- Paper bag high-rise waist
- Roll cuffed hem
- Dual button front and hidden zipper closure
- Belt loop accents
- Classic 5-pocket design
- Non-stretch denim fabric
- Fits true to size
Style Number/Barcode: 06603-0265
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Strut It Out Abstract Zebra Maxi Skirt
Perfect your vibe with the strut it out abstract zebra maxi skirt. This sheer mesh beauty flaunts a zebra print and mid-rise waist for a fierce look. Pair it with the matching top for ultimate style.
Fit & Features
- Sheer mesh fabrication lined with stretchy knit
- Mid-rise waist
- Zebra print
- Maxi length hem
- Runs true to size
Shop Matching Top: Strut It Out Abstract Zebra Tie-Front TopStyle Number/Barcode: 06501-1105
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Bliss Crochet Lace Crop Top
The cute crochet lace detailing of this crop top makes it so boho-chic! The top features a sleeveless V-neckline, adjustable spaghetti straps, a floral crochet lace design, and a cropped fit with a scalloped trim. Style with printed flare pants and espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Floral crochet lace design
- Partially smocked back
- Cropped fit, scalloped trim
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-1791
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tropical Glam Ruched Short Dress
Keep it glam on your tropical getaway with a mini dress that brings those island vibes! The dress features a tropical floral print, a sleeveless square neckline, spaghetti straps, ruching, and a short length with a rounded hem. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a straw hat.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching
- Tropical floral print
- Short length hem
- Lined smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4683
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Standout In Glam Thong Wedge Sandals
Stand out in these glam sandals while soaking up the sun! They feature a round toe, clear stone embellished thong strap, wedge sole, and a comfort foam footbed. Complete the look in a chic swimsuit and wrap.
Fit & Features
- Round toe
- Clear stone embellished thong strap
- Wedge sole
- Comfort foam footbed
- Slide-on/off styling
- Runs true to size
Style Number/Barcode: 07404-1012
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Silky Chic Kimono Tie-Front Top
Silky and so chic! Luxe up your look in this satin crop top featuring three-quarter-length kimono sleeves, a plunge V-neckline, a tie-front closure, and a cropped hem. Complete the look in trouser shorts and sandals for vacation.
Fit & Features
- Three-quarter-length kimono sleeves
- Plunge V-neckline
- Tie-front closure
- Cropped hem
- Silky satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1298
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Tide Halter Cutout Midi Dress
Flaunt this midi dress on your island getaway! Designed to accentuate your fab figure on a sleeveless, halter neck with tie closure, and sultry side cutouts on the form-fitting silhouette. Complete the look in strappy mules for a sunset dinner.
Fit & Features
- Sleeveless, halter neck, tie closure
- Side cutouts
- Partial open-back design
- Form-fitting silhouette
- Midi-length hem
- Sweater-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1313
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance