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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Getaway Retreat Sweetheart Tropical Crop Top
Getaway in this tropical crop top for the sweetest vacay vibe! This crop top features wide shoulder straps, a sweetheart neckline for a flattering look, padded bra cups for support, and a stretchy smocked back and cropped hem to flaunt your figure. Complete the look with the matching bottoms.
Shop The Matching Bottoms: Getaway Retreat High Rise Tropical Pants
Fit & Features
- Tropical print, woven fabric, sewn-in lining
- Wide shoulder straps
- Sweetheart neckline
- Padded bra cups
- Stretchy smocked back
- Cropped length
- Runs true to size
Style Number/Barcode: 06003-2504
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Little Miss Charming Strappy Back Denim Romper
Turn heads with your charm in this denim romper at concerts or weekend fun! Designed with a strappy open back, side pockets, and a pleated short hem, this romper is both stylish and functional.
Fit & Features
- Denim fabric
- Halter V-neckline, keyhole cutout
- Strappy open back, zipper closure
- Side pockets
- Pleated short hem
- Runs true to size
Style Number/Barcode: 06603-000008
Category Name: Vacation Looks
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Flowy Chiffon Midi Dress
Get the perf semi-formal look in this effortlessly chic chiffon midi dress. It features a sleeveless sweetheart neckline with a padded bust, spaghetti straps, a flattering high waist seam, and a mid-length skirt with a front slit and a flowy A-line silhouette. Style this dress with sleek earrings and cute heels.
Fit & Features
- Sleeveless sweetheart neckline
- Built-in padded bust
- Adjustable spaghetti straps
- Partially smocked back, zipper and hook-eye closure
- High waist seam, flowy A-line silhouette, front slit
- Sheer chiffon fabric, inner knit lining
- Runs true to size
Style Number/Barcode: 05101-2187
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Style Ruched Romper
Show off your flirty style in this adorable romper! Designed with a stretchy smooth knit fabric, it features a sweetheart neckline, short puff sleeves that can be worn off-the-shoulder, ruched detailing at the waist, a fit and flare silhouette, and flowy shorts with a mini skirt overlay. Complete the look with gold hoops and strappy sandals.
Fit & Features
- Smooth knit fabric, plenty of stretch
- Sweetheart neckline
- Short puff sleeves, elastic cinched hems
- Ruching at the waist, elastic seams
- Fit and flare silhouette
- Flowy shorts, mini skirt overlay
- Runs true to size
Style Number/Barcode: 06503-0987
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Fun Ruffled Mini Skort
This adorable mini skort was made for weekend fun, designed with a tiered ruffled mini-length overlay over hidden shorts. Style with the matching tie-front top for the cutest vibe.
Shop Matching Top: Weekend Fun Flutter Sleeve Tie-Front Top
Fit & Features
- Cotton woven fabric with swiss dot pattern, no stretch
- Mid-rise elasticized waist
- Tie-front adjustable drawstring
- Tiered ruffled design
- Mini-length overlay, A-line silhouette
- Hidden fitted knit shorts, moderate stretch
- Runs true to size
Style Number/Barcode: 06303-000013
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: WHITE
Available Size: S, M, L
Product Badge:- Sale
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Free Spirit Chick High-Rise Boho Flare Pants
These boho pants are for the free-spirit chicks who want to look trendy during festivals, concerts, or at parties! Made from a soft brushed knit stretchy fabric with a bohemian-inspired print, they feature a flattering high-rise elasticized waist for comfort, a hip-hugging fit, and a flared hem. Style with a cute crop top!
Fit & Features
- Bohemian-inspired print
- Brushed knit stretchy fabric
- Hip-hugging fit
- Flared hem
- Runs true to size
Style Number/Barcode: 06502-2459
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Inspired Art Abstract Bodycon Mini Dress
Bring a little extra artsy glamour to any plans in this abstract bodycon mini dress sure to inspire many compliments!
Fit & Features
- Abstract print, mesh-lined fabric
- Adjustable spaghetti straps
- Square neckline, padded bra cups
- Front ruched drawstring
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-5952
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coastal Destination Halter Tie-Front Crop Top
Go bold in this halter crop top designed to bring an alluring look with a center slit and string tie-front. Perfect for coastal vacays!
Fit & Features
- Texture knit fabric, bust knit lining
- Halter plunge V-neckline, spaghetti strap tie
- String tie-front with beaded ends
- Center slit design
- Crop hem
- Runs true to size
Style Number/Barcode: 06003-000032
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Style Faux Leather Platform Block Heels
These on-trend platform block heels are the perfect style for elevating your look! Designed with smooth faux leather material, they feature a chunky block heel for comfortable wear, an open almond-shaped toe with a wide criss-cross strap design, thin adjustable ankle and heel straps with a buckle closure, and a tall platform sole for that added height. Pair with a flowy sundress for a weekend party!
Fit & Features
- 4.5" Chunky block heel
- Faux leather upper, padded insole
- Open almond toe
- Criss-cross strap design
- Adjustable ankle and heel straps with buckle closure
- Platform sole
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4670
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Clean Lines Scoop Neck Seamless Top
This minimalistic basic top is what every girl needs for everyday styling! The crop top features long fitted sleeves, and a scoop neck, and is composed of a buttery soft knit fabric with a seamless design. Complete the look in a cute jean jacket, paper bag pants, and booties!
Fit & Features
- Long fitted sleeves
- Scoop neck
- Cropped hem
- Buttery soft knit fabric, seamless design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1534
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Luxury Cowl Neck Marble Glitter Mini Dress
Indulge in the flirty luxury of this mesh mini dress for a night on the town! Crafted from an airy mesh fabric adorned with a glam marble print with glitter streaks, this dress is ready to be the most divine at the club. Featuring a sultry cowl neckline, adjustable spaghetti straps for a custom fit, and side ruched seams along the bodycon silhouette that flaunts your figure! Complete the look with platform heels.
Fit & Features
- Marble print, glitter streaks
- Mesh fabric, sewn-in knit lining with stretch
- Adjustable spaghetti straps
- Side ruching
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-5432
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Put A Ring On It Sweater Midi Dress
A sultry take on a classic staple! This sweater midi dress features fitted long sleeves, a v-neckline, a front cutout with a ring hoop insert, and a form-hugging silhouette with a flirty front slit. Style with pointed-toe booties to complete the look!
Fit & Features
- Fitted long sleeves
- V-neckline
- Front cutout with a ring hoop insert
- Form-hugging silhouette
- Front slit, midi-length hem
- Rib-knit sweater fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1612
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Henley Formal Lace-Up Midi Dress
Special Occasion
Lace-up in a formal dress that brings the radiance to your evening! Henley features a sleeveless square neckline, spaghetti straps, a bold lace-up back, and a midi-length silhouette accented with a high-side slit. The dress is composed of a lined crepe fabric that offers a form-flattering fit with a moderate stretch. Complete look with rhinestone heels and a sphere clutch.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lace-up back
- Midi length silhouette
- High side slit
- Lined crepe fabric
- Form-hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05001-0755
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set It Off Ruffled Bodycon Dress
Set off your night with a head-turning bodycon that raises the heat! The dress features a sleeveless wrap V-neckline, spaghetti straps, a ruched body, and a mini-length silhouette with a ruffled hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels and a clutch.
Fit & Features
- Sleeveless wrap V-neckline
- Spaghetti straps
- Ruched body
- Mini length silhouette, ruffled hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4464
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Coastal Breeze Linen High Slit Maxi Skirt
Channel that coastal chic vibe with this breezy linen maxi skirt featuring a tiered design, high-cut side slit, and flowy A-line silhouette.
Fit & Features
- Linen-blend fabric
- High-rise waist
- Tiered design
- Thigh-high side slit
- Flowy A-line silhouette
- Runs true to size
Style Number/Barcode: 06301-000004
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Light Sleeveless Linen Corset Top
Keep it light and effortless in this linen corset top for a day spent under the sun! With a sleeveless V-wired neckline and tank straps, this top offers a flattering fit. The cropped hem flaunt your figure, while the linen fabric elevates the look. Style with the matching bottoms.
Shop Matching Bottoms: Keep It Light High Rise Linen Palazzo Pants
Fit & Features
- Linen woven fabric, no stretch
- Tank straps
- Cropped hem
- Multiple back hook and eye fasteners
- Runs true to size
Style Number/Barcode: 06003-2359
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Card Knit Cutout Crop Top
Match your wardrobe to your mood! This flirty crop top features long sleeves, a v-neck, and dual front twist accents and cutouts on brushed knit fabric with plenty of stretch. Style with high-rise jeans for happy hour!
Fit & Features
- Long sleeves
- V-neck
- Dual front twist accents and cutouts
- Cropped hem
- Brushed knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4554
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Classic Button-Front Henley Bodysuit
This casual classic henley bodysuit will be a new wardrobe staple! It features a V-neckline, a partial faux button-front design, short sleeves, a thong bottom with a dual snap-button closure, and a form-hugging fit. The ribbed knit fabric offers plenty of stretch. Style with high-rise denim and your fave mules.
Fit & Features
- V-neckline
- Partial faux button-front design
- Short sleeves
- Thong bottom, dual snap-button closure
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1560
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Sweet Look Sleeveless Ruffled Skater Dress
A sweet skater dress for showers or brunch! With its romantic sweetheart neckline and bust tie, you'll feel so flirty. The adjustable spaghetti straps allow for a perfect fit while the ruffled skater silhouette and short-length hem add a touch of playful charm. The partially smocked back offers added stretch. Complete the look with a heart necklace and sandals.
Fit & Features
- Gauze woven fabric with stretchy knit lining
- Sweetheart neckline, bust tie
- Adjustable spaghetti straps
- Stretchy smocked back
- Ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5499
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Fun High Rise Striped Knit Midi Skirt
Give your vacay style a dynamic upgrade in this flirty knit midi skirt perfect for a getaway or weekend fun! The skirt boasts a high-rise waist, a bodycon fit, a center back slit for movement, and a midi-length hem on pointelle knit fabric showcasing a trendy striped pattern. Complete the look with the matching top.
Shop Matching Top: Flirty Fun V-Neck Tie Striped Knit Crop Top
Fit & Features
- Pointelle knit fabric, striped pattern
- High-rise waist
- Center back slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1013
Category Name: Vacation Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Whimsical Muse Chiffon Swiss Dot Skater Dress
You'll be a chic whimsical muse in this airy chiffon skater dress! The short dress features a square neckline, short billowy puff sleeves with ruffled accents at the shoulders, an open back with an adorable bow tie-back design, and a short skater skirt with a flared-out silhouette. The lined chiffon fabric features an all-over swiss dot pattern. Style this flirty dress with classic block heels.
Fit & Features
- Square neckline
- Short puff sleeves, ruffled accents, elasticized hems
- Open-back, bow design, tie closure
- Empire waist, elastic back
- Short skater skirt, fit and flare silhouette
- Sheer chiffon fabric, swiss dot pattern, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2288
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Follow Your Heart Sleeveless Ruffled Lace Maxi Dress
Follow your heart and it'll lead you to this lace maxi dress! Perfect for bridal showers, dressy brunches, or parties. This sleeveless dress brings an allure of romance in a square neckline with adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffled silhouette. Complete the look in strappy heeled sandals.
Fit & Features
- Lace fabric, stretchy knit lining
- Adjustable spaghetti straps
- Square neckline
- Tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3382
Category Name: Vacation Looks
Price: $28.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Classic Chic Choice Trouser Shorts
These dressy woven trouser shorts are a classic chic choice for drinks with the girls! They feature a high-rise waist, belt loops, side pockets, pleated detailing, and a fitted silhouette. The woven fabric has a lightweight feel for comfortable wear. Style with a cropped blouse and strappy mules.
Fit & Features
- High-rise waist, belt loops
- Hidden front zipper, button, and hook and bar closures
- Side pockets
- Pleating
- Fitted silhouette
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06403-0260
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Intentions Cutout Mesh Mini Dress
Giving an island goddess with a hint of chaos—in the best way. The bodycon fit and hoop cutout bring the heat, while the ruffle-trim slit? Pure drama.
Fit & Features
- Mesh-lined fabric with leopard multi-print
- Cowl halter neckline with spaghetti straps
- Side cutout with hoop insert detail
- Bodycon fit with asymmetric ruffle-trim slit
- Mini-length silhouette
- Runs true to size
Style Number/Barcode: 05103-000144
Category Name: Vacation Looks
Price: $17.97 $34.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: M, L
Product Badge:- Sale