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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Flawless Floral Mesh Tie Crop Top
Keep it fresh looking flawless in this floral mesh crop top to pair with your favorite bottoms! It features an off-the-shoulder neckline, sheer peasant sleeves, a tie-front closure with a keyhole accent, and a ruched bust and fitted hem. Style with new skinny jeans to complete the look!
Fit & Features
- Off-the-shoulder neckline
- Sheer peasant sleeves
- Tie-front closure, keyhole accent
- Ruched bust
- Fitted crop hem
- Floral print, mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4413
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Whatever Rib Takes Cutout Mini Dress
Take on the day in style wearing this mini dress featuring a trendy, sleeveless, high neck, bodycon silhouette, and a cutout accent for a flash of skin. Complete the look in sunnies and sandals for the perf day date look.
Fit & Features
- Sleeveless, high neck
- Bodycon silhouette
- Cutout accent
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1270
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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A Total Vibe Halter Bodysuit
You in this sultry-chic bodysuit would be a total vibe! Featuring a sleeveless twist-front halter neckline with a center keyhole cutout at the bust, this bodysuit will elevate your basic look. Style with a faux leather skirt and mules.
Fit & Features
- Sleeveless twist-front halter neckline
- Center keyhole cutout
- Open back
- Thong bottom, dual snap-button closure
- Smooth knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4808
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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One More Moment Sweater Dress
Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless square neck, spaghetti straps that lead to an open back with lace-up closure, a form-fitting silhouette, and a high side slit atop the midi-length hem. Complete the look with sandals and sunglasses.
Fit & Features
- Sleeveless square neck, spaghetti straps
- Open back, lace-up closure
- Form-fitting silhouette
- Side slit, midi-length hem
- Sweater knit fabric, slightly sheer, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1688
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Easy Breezy In Floral Chiffon Dress
Easy, breezy, and beautiful! You'll adore this floral chiffon dress perfect for bridal showers or dressy spring parties. It features an off-the-shoulder, sweetheart neck, ruffled short-sleeve cuffs, a padded bust, a smocked back, and a flowy skater silhouette with a ruffled short hem. The dress is composed of an airy chiffon with a rose floral bouquet print and a stretchy knit lining. Complete the look in strappy sandals.
Fit & Features
- Off-the-shoulder, sweetheart neck, padded bust
- Ruffled short sleeve cuffs
- Smocked back, zipper nad hook-eye closure
- Flowy skater silhouette, ruffled short hem
- Rose floral bouquet print
- Airy chiffon, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2052
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Charm Halter Babydoll Mini Dress
A charming halter dress for dinner dates or beachside strolls. Its lightweight babydoll silhouette offers a comfortable, flowy fit, while the playful ruffle mini hem brings a flirty finish!
Fit & Features
- Woven gauze fabric, woven lining
- Sweetheart halter neckline, hoop insert, spaghetti strap tie
- Cutout keyhole accent
- Padded bra cups
- Flowy babydoll silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6087
Category Name: Vacation Looks
Price: $44.90
Availability: In Stock
Available Color: NATURAL
Available Size: L
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Cute Charm Ditsy Floral Skater Dress
Show off your cute charm in this adorable ditsy floral skater dress! It features a square neckline with a ruffled trim, a ruched bust with a tie-front detail, short puff sleeves, a fitted high waist seam, and a short flared-out skater skirt with a flowy silhouette. The lightweight woven fabric features a dainty ditsy floral print pattern. Style with espadrille sandals for a picnic date.
Fit & Features
- Square neckline, ruffled trim
- Ruched bust, tie-front detail
- Short puff sleeves, elastic cinched hems
- Back zipper, hook and eye closure
- High waist seam, short skater skirt, fit and flare silhouette
- Ditsy floral print, woven fabric, bust knit lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4854
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flourish In Floral Print Mini Dress
Flourish for spring in this dainty floral mini dress you'll love styling for casual plans! It features a sleeveless scoop neck with a tie-front bust, spaghetti straps, and a bodycon fit on stretchy rib knit fabric. Complete the look with new trendy sandals.
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Tie-front bust
- Bodycon fit
- Mini-length hem
- Dainty floral print, stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-4930
Category Name: Vacation Looks
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bae Breeze Cotton A-Line Short Dress
Enter looking like bae just breezed in! Capture cuteness in this cotton short dress featuring short puff sleeves, a square neck, an open lace-up back, and an A-line silhouette. Style with a trendy crossbody bag and heels.
Fit & Features
- Short puff sleeves
- Square neck
- Open lace-up back, zipper and hook-eye closure
- A-line silhouette
- Short-length hem
- Cotton fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4876
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dream Look Floral Ruched Mini Dress
Create your dream look for a spring date in this adorable floral mini dress! It features a sleeveless sweetheart neckline with ruching at the bust, spaghetti straps, an open back with a lace-up strappy design, ruching down the side seams, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric features a dainty rose print pattern for the prettiest look. Style with clear heels.
Fit & Features
- Sleeveless sweetheart neckline, ruching at the bust, spaghetti straps
- Open back, lace-up strappy design, tie closure
- Ruching down the side seams
- Mini-length hem, form-hugging fit
- Dainty rose print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4888
Category Name: Vacation Looks
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Picnic Time Gingham Mini Dress
You'll be the cutest girl in this gingham casual dress at the picnic! It features ruffle trim puff short sleeves, a sweetheart neck with a lace-up bust, a bodycon silhouette, and a mini-length hem on stretchy rib knit fabric. Complete the look in sandals.
Fit & Features
- Ruffle trim puff short sleeves
- Sweetheart neck, lace-up bust
- Bodycon silhouette
- Mini-length hem
- Gingham print
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-4995
Category Name: Vacation Looks
Price: $27.90
Availability: Out of Stock
Product Badge:- Sale
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Cute Flare High Rise Denim Jeans
Show off your cute style in these denim jeans you've been eyeing all over social media! They feature a flattering high-rise waist, hip-hugging fit, front seam detailing, and a flared hem. Complete the look in a trendy corset top and sandals for a casual dinner!
Fit & Features
- High-rise waist
- Hip-hugging fit
- Front seam detailing
- Flared hem
- Front button and hidden zipper closure
- Light wash denim fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06602-0434
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Remy High-Rise Destructed Shorts By Windsor Denim
Edge it up this season in the Remy jean shorts by Windsor denim! They feature a flattering high-rise waist, front distressed accents, and a destructed cut-off hem on medium-wash denim with color fading. Complete the look with a trendy crop top for a festival weekend or party!
Fit & Features
- High-rise waist
- Front distressed accents
- Destructed cut-off hem
- Front button and hidden zipper closure, belt loop accents
- Five-pocket styling
- Medium wash denim, color fading, no stretch
- Runs true to size
Style Number/Barcode: 06603-0251
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Celestial Charm Necklace Set
Layer on a boho-chic style with this celestial charm necklace set! It includes a single row snake chain necklace and a four-row layered dainty chain necklace featuring star and moon charms and rhinestone embellishments. Style with stud earrings.
Fit & Features
- Set of two necklaces
- Single row snake chain necklace
- Four-row layered dainty chain necklace
- Star and moon charms, rhinestone embellishments
- Adjustable chains, lobster clasp closures
Style Number/Barcode: 07002-1481
Category Name: Vacation Looks
Price: $3.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Bae Crew Neck Slit Maxi Dress
A cute basic maxi dress for looking trendy on your off-duty days! It features short sleeves, a crew neck, a bodycon silhouette, and a high side slit to show off some leg! The dress is composed of a brushed knit stretchy fabric. Complete the look in flat sandals and a handbag.
Fit & Features
- Short sleeves
- Crew neck
- High side slit
- Bodycon silhouette
- Maxi-length hem
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-4786
Category Name: Vacation Looks
Price: $18.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trish Cargo Wide-Leg Jeans by Windsor Denim
Create a trendy and fab everyday look with the Trish cargo wide-leg jeans by Windsor Denim. They feature a mid-rise waist, cargo-style side pockets, and a relaxed wide-leg fit. Style with a corset top and clear mules for casual weekend plans.
Fit & Features
- Mid-rise waist
- Front button closure, belt loops
- Dual front and back pockets
- Cargo-style side pockets
- Relaxed wide-leg silhouette
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0449
Category Name: Vacation Looks
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Marvel In Marble Mini Skirt
You'll be such a marvel in this marble mini skirt perfect for a girl's night out! It features a high-rise waist, all-over ruching, a mini-length hem, a curve-hugging fit, and a trendy marble print pattern on a lined mesh fabric. Complete the look with the matching bustier and heels.
Shop Matching Top: Such A Marvel In Marble Bustier
Fit & Features
- High-rise waist
- Side and back ruching
- Mini-length hem
- Curve-hugging silhouette
- Marble print
- Lined mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0807
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Brunch Eyelet Skater Dress
This adorable skater dress is a perfect pick for weekend brunch! It features a sweetheart neckline, short puff sleeves with tie accents, a high waist seam, a short skater skirt with a ruffled hem, and a fit and flare silhouette. The lightweight knit fabric features a dainty eyelet pattern for the prettiest look. Style with espadrille wedges.
Fit & Features
- Sweetheart neckline, shirring at the bust
- Short puff sleeves, cinched hems, tie accents
- High waist seam
- Short skater skirt, ruffled hem
- Fit and flare silhouette
- Eyelet knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4915
Category Name: Vacation Looks
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everlasting Pretty Floral Chiffon Skater Dress
Freshen up your closet in this pretty floral chiffon dress for a blissful day date to jaunt through a garden party! It features sheer peasant long sleeves, a smocked and stretchy V-neck bodice, a fit and flare silhouette, and a flowy short-length hem. The dress is designed with a gorgeous floral pattern on airy chiffon with a stretchy knit lining. Complete the look with strappy platform heels.
Fit & Features
- Sheer peasant long sleeves
- Smocked and stretchy V-neck bodice
- Back zipper closure
- Skater silhouette
- Flowy short-length hem
- Floral pattern, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4977
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Guest List Glam Abstract Halter Maxi Dress
All eyes on you (as it should be). With a dreamy slit and waist cutouts, this maxi dress is made for RSVPs, rooftop clinks, and compliments you’ll pretend to be shy about.
Fit & Features
- Abstract print, mesh-lined fabric, moderate stretch
- Halter cowl neckline, hoop inserts, spaghetti strap tie
- Open back
- High front ruffled trim slit
- Bodice cutout with hoop insert
- Curve-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000381
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Sunny Days Ahead Espadrille Platform Sandals
These adorable espadrille platform sandals were made for sunny spring vibes! They feature an open almond-shaped toe, a wide toe strap, an adjustable ankle and heel strap, a platform sole, and a block heel. The sandals are composed of a braided jute material with a faux leather insole. Style with a flowy floral dress!
Fit & Features
- Open almond-shaped toe
- Wide toe strap
- Adjustable ankle and heel strap, buckle detail
- Platform sole
- Block heel
- Braided jute material, faux leather insole
- Runs true to size
Style Number/Barcode: 07404-1103
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Found Love In Floral Lace Romper
Love the way you look in this breezy floral romper for spring dates and events! It features a sleeveless V-neck, adjustable spaghetti straps that cross in the back, and a lace bodice with a sheer crochet waist leading to the flowy short hem. Complete the look in strappy platform heels.
Fit & Features
- Sleeveless V-neck
- Adjustable spaghetti straps, cross-back design
- Lace bodice with sewn-in knit lining, sheer crochet waist
- Flowy short hem
- Floral print, non-stretch chiffon fabric
- Runs true to size
Style Number/Barcode: 06303-0161
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Shine Rhinestone Dainty Ring Set
Show off a trendy shine with this dainty ring set for everyday glamour! The pack features six metal rings including one thin ring with a center gemstone, one thin ring with a rhinestone embellished star design, one textured midi ring with rhinestones, one midi ring with a smiley face design, one stacked ring with sleek and twisted designs, and one statement ring with an all-around twisted design. Style with stud earrings.
Fit & Features
- Six-pack metal ring set
- One thin ring, center gemstone
- One thin ring, rhinestone star design
- One textured midi ring, rhinestones
- One midi ring, smiley face design
- One stacked ring, sleek and twisted designs
- One statement ring, all-around twisted design
Style Number/Barcode: 07004-0331
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On That Western Trend Necklace And Earrings Set
Get on that western trend with this adorable necklace and earrings set! It features a a dainty chain necklace with a single cowboy boot charm and matching cowboy boot stud earrings. Style with a distressed denim jacket for festival season!
Fit & Features
- Necklace and earrings set
- Dainty chain necklace, cowboy boot charm
- Lobster clasp closure
- Cowboy boot stud earrings
- Post-back closures
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07002-1392
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance