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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When In Floral Chiffon Smocked Crop Top
When in floral, flaunt it! Create a cute look in this chiffon crop top featuring long peasant sleeves, a ruffled sweetheart neckline, and a smocked bodice with ruched tie closure. Complete the look in jeans and heels.
Fit & Features
- Long peasant sleeves
- Ruffled sweetheart neckline
- Smocked bodice, ruched tie closure
- Floral pattern
- Chiffon fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1686
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Summer Days Polka Dot Jumpsuit
This breezy lightweight jumpsuit is perfect for casual summer days! It features a sleeveless V-neckline, spaghetti straps, a partially open back with an adjustable tie closure, and an on-trend, flowy, wide-leg fit. The airy woven fabric features an all-over adorable polka dot print. Complete the outfit with espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Partially open back, adjustable tie closure, hidden zipper, hook and eye closure
- Relaxed wide-leg fit
- Polka dot print
- Woven fabric, short woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06302-0652
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shades For Days Round Sunglasses
The perfect sunglasses for wearing on rotation! They feature a sleek plastic round frame, gradient lens, and side metal accents. Complete the look in a swim cover-up and swimsuit for the perf beach fit.
Fit & Features
- Sleek plastic round frames
- Gradient lens
- Side metal accents
- 100% UV protection
Style Number/Barcode: 07008-0966
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Day Slay Square Ombre Sunglasses
Slay all day in these cool sunglasses featuring a sleek square metal frame, ombre tint gradient lens, and rubber nose support for comfort. Complete the look in a classic denim jacket for running errands.
Fit & Features
- Sleek square metal frame
- Ombre tint gradient lens
- Rubber nose supports
- 100% UV protection
Style Number/Barcode: 07008-0964
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sea Breeze Tropical Midi Dress
Take a sunset stroll in this alluring tropical midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched detailing down one side, and a midi-length, asymmetrical hem creating a high side slit. The all-over palm leaf print will bring major vacay vibes. Style with strappy sandals and a flowy kimono.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruching down one side
- Midi-length, asymmetrical hem, side slit
- Curve-hugging silhouette
- Palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4421
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute And Classic Cuffed Denim Jacket
Layer on this cute and classic denim jacket over all your casual summer 'fits. It features a collared neckline, three-quarter length sleeves with buttons to cuff, a complete button-down front, and a cropped, fitted silhouette. Style with simple hoop earrings.
Fit & Features
- Collared neckline
- Three-quarter length sleeves, buttons to cuff
- Button-down front
- Buttoned chest pockets, side pockets
- Cropped fit
- Light wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06203-0193
Category Name: Vacation Looks
Price: $14.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Staycation High Slit Maxi Skirt
Bare it all for a saucy night out in this high-rise maxi skirt featuring a sultry front slit on a form-fitting silhouette. Complete the look in the matching bottoms.
Shop Matching Top: Staycation Twist Banded Crop Top
Fit & Features
- High-rise waist
- Front slit
- Form-fitting silhouette
- Maxi-length hem
- Sleek knit-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0597
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chill Vision Small Rectangle Sunglasses
For the days when you’re chill, but still need to serve a look. These small rectangle sunglasses are the perfect low-key statement for brunch hangs, solo city strolls, or golden hour selfies.
Fit & Features
- Small rectangular-shaped design
- Plastic frame with glossy finish
- Thin arms
- Flexible nose pads
- Tinted lenses
Style Number/Barcode: 07008-000059
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vibe Out Y2K Lace-Up Block Heels
Vibe out in 2000's style! These block heels will give your outfit a major throwback. Featuring an almond toe, block heel, a lace-up design, and a marble print. Complete the look in a cool denim jacket.
Fit & Features
- Almond toe
- Block heel
- Lace-up design
- Marble print
- Satin material
- Runs true to size
Style Number/Barcode: 07401-3894
Category Name: Vacation Looks
Price: $12.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Staycation Twist Banded Crop Top
Bare it all for a saucy night out in this crop top featuring a sleeveless V-neckline, adjustable spaghetti straps, and a sultry twisted bodice with an elasticized band. Complete the look in the matching bottoms.
Shop Matching Bottoms: Staycation High Slit Maxi Skirt
Fit & Features
- Sleeveless, V-neck, adjustable spaghetti straps
- Twisted bodice
- Elasticized band
- Cropped hem
- Sleek knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4008
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Coolest Vibe Midi Skirt
Showcase the coolest vibe in this trendy midi skirt. It features a high-rise waist with a knot-front design, a midi-length asymmetrical hem with a high side slit, and an all-over marble print pattern. Complete the look with the matching crop top.
Shop Matching Top: The Coolest Vibe Cropped Tank
Fit & Features
- High-rise waist
- Knot-front design
- Midi-length, asymmetrical hem, side slit
- Curve-hugging silhouette
- Marble print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0600
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Coolest Vibe Cropped Tank
Showcase the coolest vibe in this trendy cropped tank. It features a sleeveless square neckline, thin tank shoulder straps, a cropped, form-hugging fit, and an all-over marble print pattern. Complete the look with the matching midi skirt.
Shop Matching Bottoms: The Coolest Vibe Midi Skirt
Fit & Features
- Sleeveless square neckline
- Thin tank shoulder straps
- Cropped, form-hugging fit
- Marble print
- Lined knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4014
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunkissed Girl Slit Midi Skirt
Embrace a sunkissed glow in this midi skirt perfect for strolling the boardwalk or hitting up cocktail hour. It features a high-rise elasticized waist, form-fitting silhouette, and a high-cut side slit on stretchy knit fabric. Complete the look in lace-up sandals.
Fit & Features
- High-rise elasticized waist
- Form-fitting silhouette
- High-cut side slit
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06501-0677
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Sunset Tie-Back Crop Top
Head to a spring sunset dinner with a view in this trendy crop top! It features a square neck, elasticized tank-style straps, and an open back with tie closure on stretchy, rib-knit fabric. Complete the look in the matching skirt.
Shop Matching Skirt: Spring Sunset Slit Maxi Skirt
Fit & Features
- Sleeveless, square neck
- Elasticized tank-style straps
- Cropped hem
- Open-back, tie closure
- Stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 06001-4070
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Sunset Slit Maxi Skirt
Head to a spring sunset dinner with a view in this maxi skirt! It features a high-rise waist, bodycon silhouette, and a sultry front slit on stretchy, rib-knit fabric. Complete the look in the matching top.
Shop Matching Top: Spring Sunset Tie-Back Crop Top
Fit & Features
- High-rise waist
- Bodycon silhouette
- Front slit
- Maxi-length hem
- Stretchy, rib-knit fabric
- Runs true to size
Style Number/Barcode: 06501-0626
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Florals Short Dress
Keep it pretty in a short dress that brings the charm! The dress features a pretty daisy print, a halter neck with neck ties, a square-neck smocked bodice, and a triple-row bar strap design at the back. The slim fit bodice leads to a fluttery A-line short-length hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules.
Fit & Features
- Halter neck with adjustable neck ties
- Square-neck smocked bodice
- Triple-row bar strap design
- Floral print
- A-line, short length hem
- Lined lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4401
Category Name: Vacation Looks
Price: $46.90
Availability: Out of Stock
Product Badge:- Sale
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Tropical Nights V-Neck Midi Dress
Enjoy your nights in paradise in this tropical floral midi dress featuring a sleeveless, v-neck, adjustable criss-cross spaghetti straps, and a bodycon silhouette leading to the asymmetrical slit hem. Complete your vacay look in strappy heels.
Fit & Features
- Sleeveless, v-neck
- Adjustable criss-cross spaghetti straps
- Bodycon silhouette
- Asymmetrical slit, side ruching
- Midi-length hem
- Tropical floral print, texture-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-1455
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Eye Of The Tiger Bandeau Crop Top
It's the eye of the tiger it's the thrill of wearing this cute bandeau crop top for your next island vacay! It features a sleeveless, strapless neckline with a flirty front knot-tie and a smocked back. Complete the look in the matching bottoms.
Shop The Matching Bottoms: Eye Of The Tiger Palazzo Pants
Fit & Features
- Sleeveless, strapless neckline
- Front knot-tie closure
- Smocked back, crop hem
- Tiger print
- Chiffon-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1742
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Tide Tropical Mini Skirt
Feel the island breeze and enter paradise in this tropical mini skirt! It features a high-rise elasticized waist, a faux-wrap front, and a bodycon silhouette. Complete the look in the matching top.
Shop Matching Top: Island Tides Tropical Tie-Front Top
Fit & Features
- High-rise elasticized waist
- Faux wrap front
- Bodycon silhouette
- Mini-length hem
- Tropical print fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0638
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Eye Of The Tiger Palazzo Pants
It's the eye of the tiger it's the thrill of wearing these cute palazzo pants for your next island vacay! It features a high-rise waist, a side hidden zipper closure, and a flowy palazzo-style leg. Complete the look in the matching top.
Shop The Matching Top: Eye Of The Tiger Bandeau Crop Top
Fit & Features
- High rise waist
- Side hidden zipper closure
- Flowy palazzo-style leg
- Tiger print
- Chiffon-lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0633
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Island Tides Tropical Tie-Front Top
Feel the island breeze and enter paradise in this tropical tie-front top! It features long bishop sleeves, a plunge V-neck, and a cropped hem. Complete the look in the matching skirt.
Shop Matching Skirt: Island Tide Tropical Mini Skirt
Fit & Features
- Long bishop sleeves
- Plunge V-neck
- Tie-front closure
- Cropped hem
- Tropical print fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0308
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry For The Summer Crochet Halter Mini Dress
Create a sultry look for the summer in this sheer crochet mini dress featuring a halter V-neckline with wooden beaded accents and a short, curve-hugging silhouette to flaunt your figure.
Fit & Features
- Sheer crochet knit fabric, moderate stretch
- Sleeveless V-neckline, wooden beaded accents
- Tie-back halter straps, wooden beaded accents
- Partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000063
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Sheer crochet knit fabric, moderate stretch
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In Season Floral Off-The-Shoulder Bustier
Always in season and never dries out! Look fresh in this floral off-the-shoulder bustier featuring a fold-over, sweetheart bodice, detachable spaghetti straps, a built-in padded bust with underwire, front hook-eye closures, and flexible boning along the cropped hem. Complete the look in faux leather leggings for a chic-edgy vibe.
Fit & Features
- Foldover, off-the-shoulder neck
- Sweetheart bodice, detachable spaghetti straps
- Built-in padded bust with underwire
- Front hook-eye closures, flexible boning
- Cropped hem
- Ditsy floral pattern, woven-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1758
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Made For You Tie Front Bandeau Top
This bandeau top was made for you on vacation or pretending while sipping on cocktails poolside! It features a strapless, sleeveless, neckline with a flirty tie-front and a smocked back panel. Complete the look in the matching bottoms.
Shop Matching Bottoms: Made For You High Rise Palazzo Pants
Fit & Features
- Strapless, sleeveless neckline
- Tie-front
- Smocked back
- Textured lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06001-4095
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale