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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Keepin' It Cute Denim Romper
Keep your summer look cute and on-trend with this adorable denim romper! It features short puff sleeves, a sweetheart neckline with a tie-front and keyhole cutout, a high waist seam, and a fitted silhouette. Complete the outfit with strappy sandals and a crossbody purse.
Fit & Features
- Short puff sleeves, elastic cinched hems
- Sweetheart neckline
- Tie-front, keyhole cutout
- Hidden back zipper and hook and eye closure
- High waist seam, fitted silhouette
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0206
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeten Up Straw Block Heels
Sweeten up any look in these heels adorned with a unique straw block heel and trendy crisscross straps. Style with a sundress for any daytime outings!
Fit & Features
- 3" Straw block heel
- Square toe
- Crisscross straps
- Adjustable ankle strap, buckle closure
- Faux leather upper material
- Runs true to size
Style Number/Barcode: 07401-000216
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Mode Straw Crossbody
Step into vacay mode with a crossbody that keeps it casual and cute! The crossbody features a rectangular body, a straw material body, a top fasten closure, and a faux leather shoulder strap. Complete look with a fab matching set.
Fit & Features
- Rectangular body
- Straw body
- Top fasten closure
- Faux leather shoulder strap
Style Number/Barcode: 07203-0574
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flower Power Multi-Tassel Earrings
Radiate a gorgeous vibe with floral earrings that enhance your outfits! The earrings feature a large flower design on post with a center rhinestone, a multi-tiered tassel design, and a post-back closure. Complete the look with a ruched mini dress and mules.
Fit & Features
- Flower design on post
- Center rhinestone
- Multi-tiered tassels
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged
Style Number/Barcode: 07001-0680
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fab And Fluttery Satin Butterfly Scarf
Keep it fab and fluttery with a cute scarf that accents your look! The versatile scarf can be styled as a head wrap, top, and traditional wear. The scarf features a pretty butterfly print and is composed of a satin-like material. Complete look with high waist jeans.
Fit & Features
- Butterfly print
- Oversized
- Satin-like fabric, no stretch
- Can be worn in multiple ways
Style Number/Barcode: 07305-0300
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fab Floral Cinched Mini Skirt
Keep it fab with a floral skirt that brings the charm to your look. The skirt features a high-rise waist, a ditsy floral print, a cinched ruched body, a mini side slit, and a mini-length silhouette. The skirt is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with the matching crop top.
Shop Matching Top: Fab Florals Flutter Sleeve Tie Front Top
Fit & Features
- High rise waist
- Ditsy floral print
- Cinched ruched body
- Mini side slit
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06501-0409
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Oversized Floppy Straw Hat
Relax underneath a cabana with a big floppy hat to style tresses with. The hat features a fitted top with a wide brim and is composed of a straw-like material. Complete the look with a swimsuit and coverup.
Fit & Features
- Fitted top
- Wide brim
- Straw-like material
Style Number/Barcode: 07302-0356
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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West Coast Graphic Tee
Rep the west coast in style with this trendy graphic tee! It features a crew neckline, short sleeves, a mid-length, form-hugging fit, and a center graphic that reads "West Coast." Complete your look with biker shorts and cute sneaks.
Fit & Features
- Crew neckline
- Short sleeves
- Mid-length hem
- Form-hugging fit
- Center graphic that reads "West Coast"
- Jersey knit fabric with plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-0759
Category Name: Vacation Looks
Price: $4.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Timeless Beauty Crochet And Gauze Jumpsuit
Keep it timelessly gorge with a jumpsuit that stuns! It features a lace-lined bodice with a deep V neckline, adjustable spaghetti straps that cross at the back, a wide crochet panel at the waist, and flowy, pant legs made of a textured woven fabric. Jumpsuit offers a form-hugging fit with minimal stretch. Complete look with wedges and a floppy hat.
Fit & Features
- Sleeveless V-neckline
- Floral lace bodice
- Adjustable spaghetti straps, cross at back
- Unlined crochet panel at the waist
- Flowy long gauze knit pants
- Form-hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 06302-0175
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Stunner Chiffon Smocked Top
Keep it stunning in charming florals that keep your look so cute! The top features a smocked off the shoulder neckline, long bell sleeves with tiered ruffles, a floral print, and a smocked cropped hem. The top is composed of a semi-sheer chiffon fabric that offers a relaxed fit with a slight stretch. Complete the look with a mini skirt and mules.
Fit & Features
- Smocked off the shoulder neckline
- Long bell sleeves with tiered ruffles
- Floral print
- Smocked crop top
- Semi-sheer chiffon fabric
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 06003-1220
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gleam and Glitz Rhinestone Sandals
Upgrade your sandals with a pretty hint of sparkle! The sandals feature an open back, a rhinestone embellished ankle strap, an open toe with a rhinestone strap over the toe. The sandals feature a flat faux leather sole. Complete look with a skater romper and door knocker earrings.
Fit & Features
- Open back
- Rhinestone embellished ankle strap
- Open toe with rhinestone strap
- Faux-leather sole
Style Number/Barcode: 07404-0763
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Distressed Drama Denim Mini Skirt
Bring the drama to your look with a denim skirt that slays! The skirt features a high-rise waist, a zippered center front, a traditional five-pocket with belt loop design, heavy distressing, and a mini-length silhouette. Complete look with a crop top and wedges.
Fit & Features
- High rise waist
- Zippered center front
- Traditional five-pocket with belt loop design
- Heavy distressing
- Mini length silhouette
- Denim
- Form hugging fit, runs true to size
Style Number/Barcode: 06601-0045
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Rise Super Destructed Cutoff Denim Shorts by Windsor Denim
Feeling extra? These high waist shorts by Windsor Denim are pef for channeling a bold look! The shorts feature a high-rise waist, a single button with zipper closure, a traditional-five pocket with belt loop design, heavy destruction throughout, and a cutoff hem. Complete look with a crop top.
Fit & Features
- High rise waist
- Heavy destruction
- Cutoff hem
- Single-button with zipper closure
- Traditional five-pocket with belt loop design
Style Number/Barcode: 06603-0157
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Moving On Up Platform Block Heels
Move on to the next level with chic heels that command attention! The heels feature an open back, clear strap at the heel, adjustable ankle strap, clear strap over the toe, an open almond toe, a wide platform, and a block heel. Complete the look with a floral top and ruffled skirt.
Fit & Features
- Open back
- Clear strap at the heel
- Clear adjustable ankle strap
- Open almond toe
- Wide platform
- Block heel
- Faux leather material
Style Number/Barcode: 07401-2762
Category Name: Vacation Looks
Price: $18.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Enchanting Floral Maxi Dress
You will look effortlessly enchanting in this stunning floral maxi dress! It features adjustable spaghetti straps, a square neckline with a ruffled trim, a stretchy smocked bodice, and a lace-up back. The elastic-banded high waist flows out to a floor-length skirt with an A-line silhouette and a thigh-high slit. Complete the look with dainty earrings and cute wedges.
Fit & Features
- Adjustable spaghetti straps
- Square neckline, ruffled trim
- Stretchy smocked bodice, lace-up back
- Elastic-banded high waist
- Floor-length skirt, A-line silhouette, high slit
- Floral printed sheer chiffon fabric, knit lining
- Runs true to size
Style Number/Barcode: 05101-0998
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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She's A Vision Abstract Cowl Slit Maxi Dress
Make a statement and turn heads in this abstract maxi dress on vacation or at a chic pool party! The cowl neck, adorned with hoop trims, adds a touch of glamour, while the high side slit and maxi length hem elongate your silhouette and add a hint of allure.
Fit & Features
- Abstract print, stretchy knit fabric
- Cowl neckline with hoop trims, spaghetti strap
- Open strappy back
- High side slit, hoop insert
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6084
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Heart Of Bloom Ditsy Floral Mini Dress
Go full bloom with a pretty mini dress! The dress features a sleeveless square neckline, a tie-front accent, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.
Fit & Features
- Sleeveless sweetheart neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, form-hugging fit
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2041
Category Name: Vacation Looks
Price: $18.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild Style Animal Print Maxi Skirt
Showcase a wild and chic style this season with this trendy maxi skirt. It features a high-rise elastic-banded waist, a maxi length, and a sultry thigh-high front slit. The stretchy knit fabric has an all-over animal print for a bold vibe. Complete your look with a basic bodysuit and mules.
Fit & Features
- High-rise elastic-banded waist
- Maxi length
- High front slit
- Animal print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0375
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bohemian Flair Tie-Back Crop Top
Give off a stylish bohemian flair in this stunning crop top! It features a deep V neckline, long blouson sleeves, a tie-back accent, and a cropped, form-hugging fit. The lightweight printed woven fabric has no stretch. Complete your look with high-rise denim shorts and strappy sandals.
Fit & Features
- Deep V neckline
- Long blouson sleeves
- Tie-back detail
- Cropped, form-fitting style
- Woven fabric with no stretch
- All-over boho-inspired print
- Runs true to size
Style Number/Barcode: 06003-1247
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Textures Cropped Tank
Keep it trendy with a tank top that is perf for lounging in. The tank top features a sleeveless square neckline, tank shoulder straps, and a cropped hem. The tank top is composed of a waffle-knit fabric that offers a relaxed fit with slight stretch. Complete look with the matching shorts and matching duster.
Shop Matching Shorts: Trendy Textures High Waist Shorts
Shop Matching Duster: Trendy Textures Long Duster
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Cropped hem
- Waffle knit fabric
- Relaxed fit, slight stretch
- Runs true to size
Style Number/Barcode: 06001-3170
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Just My Type Clear Cork Wedges
These wedges are just your type, girl! The wedges feature an open back with a clear PVC heel strap, an adjustable ankle strap, an open almond toe with a clear PVC strap, and a cork wedge heel. Complete look with a ruffled mini dress and a sheer duster.
Fit & Features
- Open back with clear PVC heel strap
- Adjustable faux leather ankle strap
- Open almond toe
- Clear PVC strap over the toe
- Cork wedge heel
Style Number/Barcode: 07406-0234
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic And Chic Two-Tone Sandals
These basic and chic faux leather sandals are a wardrobe must-have this season. They feature an open round toe, a wide strap and thin adjustable ankle strap with a two-tone design, and an open back. Pair these flat sandals with a basic bodysuit and high-rise denim shorts.
Fit & Features
- Open round toe
- Wide strap
- Thin adjustable ankle strap
- Two-tone design
- Open back
- PU material
- Runs true to size
Style Number/Barcode: 07404-0747
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Textures Long Duster
Keep it trendy a duster that is perf for lounging in. The duster features a draped open front, long sleeves, and a flowy long length. The duster is composed of a waffle-knit fabric that offers a relaxed fit with slight stretch. Complete look with the matching tank top and shorts.
Shop Matching Tank Top: Trendy Textures Cropped Tank
Shop Matching Shorts: Trendy Textures High Waist Shorts
Fit & Features
- Draped open front
- Long sleeves
- Waffle knit fabric
- Relaxed fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0167
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Layered In Glam Triple-Layered Body Chain Jewelry Set
Layer up in glam with a body chain jewelry set that adds that chic touch to your look! The set features a triple-layered design that drapes around the body. It includes a short necklace with a rhinestone adorned bar charm and a longer necklace with a rhinestone adorned round charm. The body chain features a center V-shaped rhinestone embellishment and a draped design. Complete the look with a swimsuit.
Fit & Features
- Jewelry set, triple-layer design
- Rhinestone adorned bar charm necklace
- Rhinestone adorned round charm necklace
- Body chain with a V-shaped rhinestone accent
- Draped, wrap-around design
- Lobster clasp closures
Style Number/Barcode: 07002-0756
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free