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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Trip To Paradise Tropical Print Maxi Dress
This bold and alluring tropical print maxi dress calls for a trip to paradise! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back design, a floor-length hem with a thigh-high front slit, and a flowy silhouette. The smooth knit fabric showcases a tropical palm leaf print. Style with strappy sandals for sunset drinks.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back design
- High waist seam
- Floor-length hem, high front slit, flowy silhouette
- Tropical palm leaf print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5025
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Beach Babe Tie-Front Top
Style up this breezy tie-front top for a total beach babe look! The lightweight gauze top features long peasant sleeves with cinched hems, a V-neckline with a tie-front design, a fitted, cropped hem, and a subtle palm leaf print. Wear it alone with denim shorts or as a cover-up over your swimsuit!
Fit & Features
- Long peasant sleeves, cinched hems
- V-neckline
- Tie-front design
- Fitted, cropped hem
- Palm leaf print
- Gauze fabric
- Runs true to size
Style Number/Barcode: 06204-1236
Category Name: Vacation Looks
Price: $17.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild And Chic Zebra Print Mini Sweater Dress
Add a wild flair to your everyday look with this chic zebra print sweater dress. It features a sleeveless V-neckline, halter straps with a tie-back design, an open back, a mini-length hem, and a curve-hugging fit. The sweater knit fabric offers a moderate stretch. Style with a mini handbag and clear mules for a fashion-forward look.
Fit & Features
- Sleeveless V-neckline
- Halter straps, tie-back design
- Open back
- Mini-length hem
- Curve-hugging silhouette
- Zebra print, sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1699
Category Name: Vacation Looks
Price: $3.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lasting Impression Sheer Mesh Maxi Dress
Leave a lasting impression showing off your gorgeous curves in this maxi dress designed with a partially sheer look that makes jaws drop!
Fit & Features
- Partially sheer mesh fabric
- Sweetheart neckline
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05103-000165
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Breeze Tropical Print Midi Skirt
Feel the island breeze as you stroll past the waves in this tropical print midi skirt. It features a high-rise waist, a hip-hugging fit, a midi-length hem with an alluring high side slit, and a flowy A-line silhouette. The smooth and stretchy knit fabric features a bold tropical palm leaf print. Style with a crop top and sandals.
Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Midi-length hem, high side slit
- Flowy A-line silhouette
- Tropical palm leaf print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0843
Category Name: Vacation Looks
Price: $11.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Bit Of Sparkle Rhinestone Aviator Sunglasses
Accessorize your 'fit with a bit of sparkle with these aviator sunglasses! They feature a rhinestone trim, a sleek metal frame, rubber nose supports, and tinted lenses with UV protection. Complete the look with a trendy rhinestone denim jacket for a summer festival or concert!
Fit & Features
- Rhinestone trim
- Sleek metal frame
- Rubber nose supports
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-0994
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pleasure's All Mine Wooden Platform Mules
Your feet will be pleased to meet these platform mules perfect for everyday styling! They feature a faux leather footbed, almond toe, wide foot strap, and a wood-inspired sole. Style with a chic crossbody bag for brunch or wine tasting!
Fit & Features
- Almond toe
- Wide foot strap
- Wood-inspired platform sole
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07401-4217
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Is Here Oversized Round Sunglasses
Summer is here, and these chic oversized sunglasses will style perfectly with all your casual looks. They feature a round shape with a thin metal frame, a chain-link design on the arms, and tinted lenses. Pair with a layered charm necklace.
Fit & Features
- Oversized round shape
- Thin metal frame
- Chain-link design on the arms
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1013
Category Name: Vacation Looks
Price: $3.96 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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La Quinta Ditsy Floral Rib Knit Mini Dress
Let your love for floral bloom in this rib knit mini dress perfect for a visit to the flower fields! It features a ruffle trim sweetheart neckline and puff short sleeves, a flirty bust lace-up, a bodycon silhouette, and a mini-length hem. Complete the look in cute flat sandals and earrings.
Fit & Features
- Ruffle trim sweetheart neckline
- Ruffle trim puff short sleeves
- Bust lace-up
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print, stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 05102-5171
Category Name: Vacation Looks
Price: $5.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Instantly Fab Oversized Square Sunglasses
You'll look instantly fab when you accessorize your everyday looks with these oversized sunglasses. They feature a square-shaped design with a plastic frame, textured gold detailing on the sides, and tinted lenses. Style with a chic handbag.
Fit & Features
- Oversized square-shaped design
- Plastic frame
- Textured gold detailing
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1021
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drive Down The Coast Oversized Square Sunglasses
These trendy oversized sunglasses are perfect for a breezy drive down the coast! They feature a square-shaped design with a tortoiseshell plastic frame, a sleek gold bar accent at the top, and tinted lenses. Style with a flowy sundress.
Fit & Features
- Oversized square-shaped design
- Tortoiseshell plastic frame
- Gold bar accent
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1022
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Beauty Chiffon Ruffle Trim V-Neck Maxi Dress
Enter every soiree looking blissfully beautiful in this chiffon maxi dress! Featuring a sleeveless V-neck with ruffle trim, adjustable spaghetti straps with a tie-back design, and a flattering babydoll-style silhouette, front slit, and maxi-length hem. Complete the look in lace-up stiletto heels and dainty earrings.
Fit & Features
- Sleeveless V-neckline with ruffle trim
- Adjustable spaghetti straps, tie-back design
- Babydoll-style silhouette
- Front slit accent
- Maxi-length hem
- Airy chiffon fabric, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2353
Category Name: Vacation Looks
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Follow The Sun Sweetheart Mini Dress
Dare to bare some skin on a sunny day in this flirty casual mini dress for hanging by the beach or downtown! It features a sleeveless sweetheart neckline, spaghetti straps, a bust tie with a keyhole accent, and flattering side ruched seams that accentuate your curves along the bodycon fit. Complete the look with cute sandals.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Bust tie, keyhole accent
- Side ruched seams, bodycon fit
- Mini-length hem
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5127
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Obsessed Strappy Platform Sandals
You'll be so obsessed with these edgy-chic platform sandals! They feature a square toe, a double-banded strap design, an adjustable ankle strap, a heel strap, and a flat platform sole. Style these sleek faux leather sandals with a crossbody bag.
Fit & Features
- Square-shaped toe
- Double-banded strap design
- Adjustable ankle strap, buckle detail
- Heel strap
- Flat platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1113
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring It One Lace Ruffle Strap Mini Dress
Put a spring in your step in this lace mini dress for an adorable party look! It features a sleeveless square neckline, half ruffled straps and half adjustable spaghetti straps, an open back with a tie closure, a side pleated seam, and a bodycon silhouette with an asymmetrical wrap hem. Complete the look with a dainty necklace for a bridal shower or graduation!
Fit & Features
- Sleeveless square neck
- Half ruffled straps, half adjustable spaghetti straps
- Open back with tie closure
- Side pleated seam, bodycon silhouette
- Asymmetrical wrap mini-length hem
- Lace fabric, stretchy knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2142
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Heart Eyes Statement Sunglasses
You'll have major heart eyes for these adorable statement sunglasses! They feature heart-shaped pink-tinted lenses with a dripping design, sleek metal arms, and rubber nose pads for support. Style with hoop earrings for a cool summer festival look.
Fit & Features
- Heart-shaped pink-tinted lenses
- Dripping design
- Thin metal arms
- Rubber nose pads
Style Number/Barcode: 07008-1017
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casually Cool High-Rise Denim Skort
Keep your everyday 'fits casually cool with this high-rise denim skort featuring a mini-length overlay with a faux wrap-front design and hidden shorts. Style with a graphic tee and sneakers!
Fit & Features
- Cotton-blend denim fabric, minimal stretch
- High-rise waist
- Back zipper with hook-eye closure, dual back pockets
- Mini-length overlay, faux wrap-front design, short slit
- Hidden fitted shorts
- Skort in size small has a 9.5" front rise with a 2" inseam
- Runs true to size
Style Number/Barcode: 06603-000005
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Essential Mesh Long Kimono
Bring it back to basics with cute layered looks with a flowy kimono! The kimono features a draped open front, long kimono sleeves, and a flowy long length. The kimono is composed of a sheer mesh fabric that offers a relaxed fit with a moderate stretch. Complete the look with a mini dress and sandals.
Fit & Features
- Draped open front
- Long kimono sleeves
- Flowy long length
- Sheer mesh fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0382
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachside Beauty Smocked Bra Top
This adorable bra top is a must-have for a beachside vacay. It features a sleeveless sweetheart neckline, adjustable spaghetti straps for a customized fit, an all-over-smocked design, and a fitted cropped hem. Style with the matching button-down top and distressed denim shorts for a casual summer vibe.
Shop Matching Top: Beachside Beauty Button-Down Top
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- All-over stretchy smocked design
- Fitted cropped hem
- Woven fabric
- Runs true to size
Style Number/Barcode: 06003-2120
Category Name: Vacation Looks
Price: $3.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachside Beauty Button-Down Top
This adorable button-down top is a must-have for a beachside vacay. It features a collared neckline, long sleeves with buttons to cuff, a complete button-down front, and a relaxed fit. Style with the matching bra top and distressed denim shorts for a casual summer vibe.
Shop Matching Top: Beachside Beauty Smocked Bra Top
Fit & Features
- Collared neckline
- Long sleeves, single buttons to cuff
- Button-down front
- Relaxed fit
- Smooth woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-2121
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Cool Crew Neck Mini Dress
Keep it cool and casual in this effortless knit mini dress for hangs with friends! It features short sleeves, a crew neck, a bodycon silhouette, and a ruched drawstring that lets you customize the style. The dress is composed of a stretchy brushed knit fabric. Complete the look in cute flat sandals.
Fit & Features
- Short sleeve, crew neck
- Bodycon silhouette
- Ruched, adjustable drawstring
- Bodycon silhouette
- Mini-length hem
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4856
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flaunt It Girl V-Neck Twist Crop Top
Flaunt your cute self in this crop top featuring short sleeves, a V-neck, a twisted bodice, and a fitted hem on stretchy rib fabric. Style with high-rise pants to complete the look for a lunch with friends!
Fit & Features
- Short sleeves
- V-neck
- Twisted bodice
- Crop fitted hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 06001-4816
Category Name: Vacation Looks
Price: $4.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Summer Style Wrap Midi Skirt
Show off a breezy boho summer style with this lightweight woven midi skirt. It features a high-rise waist with a side knot detail, a wrap silhouette creating a subtle front slit, a midi-length hem, and a relaxed fit. The woven fabric features a bohemian-inspired diamond multi-print pattern. Complete the look with a basic bodysuit and strappy sandals.
Fit & Features
- High-rise waist, side knot detail
- Back zipper closure
- Wrap silhouette, front slit
- Midi-length hem, relaxed fit
- Bohemian-inspired diamond multi-print pattern
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0164
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Remy High-Rise Lace-Up Shorts by Windsor Denim
Spice up the denim scene in the Remy shorts by Windsor Denim! They feature a flattering high-rise waist with a lace-up placket, a form-hugging fit, and an edgy raw cut-off hem on premium denim fabric with minimal stretch. Complete the look in a cool graphic top for a concert!
Fit & Features
- High-rise waist
- Lace-up placket
- Form-hugging fit
- Raw cut-off hem
- Four-pocket styling, belt loop accents
- Premium denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0328
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free