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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Pretty Glam Rhinestone Pearl Buckle Slide Sandals
Adorn your feet in these glam rhinestone faux pearl slide sandals with dual buckle straps and a comfortable footbed. Pair with a tote bag for a beach day.
Fit & Features
- Round toe
- Dual buckle straps with rhinestone, faux pearl trim
- Comfortable footbed
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1284
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Remy High Rise Cut Off Shorts By Windsor Denim
Showcase your cute curves in the Remy jean shorts by Windsor Denim! They feature a flattering high-rise waist, cut-off style hem, and a vintage-inspired color fade effect on premium denim fabric. Complete the look in a flirty crop top for a beach day.
Fit & Features
- High-rise waist
- Cut-off style hem
- Color fade effect
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Form-hugging, denim fabric
- Fits true to size
Style Number/Barcode: 06603-0278
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cancun Vacay Tropical Slit Maxi Skirt
Cancun isn't ready for this one! Jet set on vacay in this tropical maxi skirt featuring a high-rise elasticized waistband, a front high slit, floral and leaf pattern, and a maxi-length hem on gauze woven fabric. Style with the matching tropical top.
Shop Matching Top: Cancun Vacay Tropical Multi-Wear Top
Fit & Features
- High-rise elasticized waistband
- Front high slit
- Floral and leaf pattern
- Maxi-length hem
- Relaxed silhouette
- Gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0078
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cancun Vacay Tropical Multi-Wear Top
Cancun isn't ready for this one! Jet set on vacay in this tropical halter top featuring multi-wear straps so you can style it as a halter or tube top, floral and leaf pattern, and a cropped hem. Style with the matching tropical maxi skirt.
Shop Matching Skirt: Cancun Vacay Tropical Slit Maxi Skirt
Fit & Features
- Multi-wear straps
- Cropped hem
- Back smocked panel
- Floral and leaf pattern
- Gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1297
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chill Factor Paisley Boho Pants
Easy, breezy, and so chill in these paisley boho pants featuring a high rise waist, form-fitting silhouette, and a flared hem. Complete the look in a cute crop top for spring festivals.
Fit & Features
- High rise waist
- Form-fitting silhouette
- Flared hem
- Paisley boho-inspired print
- Fits true to size
Style Number/Barcode: 06502-0869
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Natural Beauty Tropical Maxi Dress
Explore a tropical island looking naturally beautiful in this palm print maxi dress featuring a sleeveless, square neck, halter straps, an open back with tie, bodycon silhouette, and a front twist accent atop a sultry slit. Complete the look in a straw floppy hat.
Fit & Features
- Sleeveless, square neck, halter straps
- Open-back with tie
- Bodycon silhouette
- Front twist accent and slit
- Maxi-length hem
- Tropical palm print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4720
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Times Marble Halter Dress
Let the good times flow in this marble print mini dress perfect for vacation and sipping mojitos! It features a sleeveless, halter neckline with a ruched drawstring and tie closure, a cutout bodice, and a form-hugging fit on the knit-lined fabric. Complete your fab look with lucite mules.
Fit & Features
- Halter neckline, ruched drawstring, tie closure
- Cutout bodice
- Form-hugging fit
- Mini-length hem
- Marble print knit-lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4531
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Resort Ready Palm Print Mini Dress
You'll be ready for your getaway at the resort with this tropical mini dress in your arsenal! It features a sleeveless square neck, sleek spaghetti straps, a palm print, and a curve-hugging silhouette. Complete your vacay look in espadrille wedges.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Curve-hugging silhouette
- Mini-length hem
- Palm print
- Soft brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4681
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sangria Please Striped Wide Leg Pants
Can't you imagine wearing this striped halter top while sipping on a sangria? Set the tone for vacay-ready in these striped pants featuring a high-rise waist, paper bag style, and a wide-leg silhouette. Complete the look in the matching top.
Shop The Matching Top: Sangria Please Striped Halter Top
Fit & Features
- High-rise elasticied waist
- Paperbag style
- Wide leg silhouette
- Striped pattern
- Gauze woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06302-0613
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Slash Of Style Cutout Crop Top
Stand out from the crowd in this elevated basic crop top featuring cap sleeves, a crew neck, and trendy cutout accents, and a fitted hem. Complete the look in distressed jeans for a casual fit.
Fit & Features
- Cap sleeves
- Crew neck
- Cutout accents
- Fitted crop hem
- Brushed knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4378
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Set Sail Tie-Front Crop Top
Get ready to set sail on a sunset cruise in this breezy crop top. It features half-length kimono-style sleeves, a V-neckline, a tie-front design, and a cropped, relaxed fit. Style this top with high-rise shorts.
Fit & Features
- Half-length kimono-style sleeves
- V-neckline
- Tie-front
- Cropped, relaxed fit
- Woven gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1187
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Social Lite Linen Envelope Skort
A social lite such as yourself needs this trendy linen skort for looking fab on the go! It features a high-rise waist with a front side button closure and an envelope-style overlay on texture linen-blend fabric. Complete the look in a boho floral top and heels.
Fit & Features
- High-rise waist, back elastic band
- Front side button closure
- Envelope-style overlay
- Shorts lining
- Texture linen-blend fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0193
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Press Pause Paper Bag Woven Shorts
Press pause and admire how stylish you'll be in these woven shorts featuring a trendy, paper bag high-rise waist, tie-front belt, pleat detailing, a four-button up closure, side pockets, and a form-fitting silhouette. Complete the look in a basic tank top and espadrille wedges.
Fit & Features
- Paper bag high-rise waist
- Tie-front belt
- Pleat detailing
- Four button-up closure, side pockets
- Form-fitting silhouette
- Woven Tencel fabric, no stretch
- Runs true to size
Style Number/Barcode: 06303-0192
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Perfectly Distressed Oversized Denim Jacket
This trendy denim jacket is perfectly distressed for that cute and casual vibe! It features a collared neckline, long sleeves, a button-down front, buttoned chest pockets, destructed details, and an oversized fit. Layer this jacket over a mini dress and complete the look with your fave mules.
Fit & Features
- Collared neckline
- Long sleeves, single-button details
- Button-down front
- Buttoned chest pockets, side pockets at the waist
- Distressed detailing
- Light wash denim fabric, no stretch
- Oversized fit
Style Number/Barcode: 06203-0453
Category Name: Vacation Looks
Price: $17.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Out Of Office Gradient Oversized Sunglasses
These sunnies say “catch me on a yacht”—even if it’s just brunch. With oversized gradient lenses and glam hardware, these sunglasses are made for low-effort luxe and spontaneous selfies.
Fit & Features
- Rimless square-shaped oversized design
- Metal chain-link detail on the arms
- Flexible nose pads
- Gradient-tinted lenses
Style Number/Barcode: 07008-000058
Category Name: Vacation Looks
Price: $10.90
Availability: Out of Stock
Product Badge:- Ships Free
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I've Got Needs Scoop Neck Crop Top
This cute, versatile crop top is ready to fulfill all of your outfit needs! It features a sleeveless, scoop neck, tank straps, crafted from stretchy rib-knit lined fabric. Complete the look in denim shorts and sneakers.
Fit & Features
- Sleeveless, scoop neck
- Tank straps
- Cropped hem
- Rib-knit lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1235
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Carefree Vibes Chic Satin Kimono
Showcase carefree vibes this summer season in this chic satin kimono. It features half-length kimono-style sleeves, an open front, a flowy, relaxed fit, side slit accents, and fringe detailing at the hem. Style over a basic bodysuit and cutoff denim shorts.
Fit & Features
- Half-length kimono-style sleeves
- Open front
- Flowy, relaxed fit
- Side slits
- Fringe detailing at the hem
- Smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1397
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Chic And Sleek Sunglasses
Keep your summer look chic and sleek with these on-trend shades! The sunglasses feature hexagon-shaped lenses with a gold metal trim, thin arms, and tinted lenses. Style with hoop earrings.
Fit & Features
- Hexagon-shaped lenses
- Gold metal trim
- Thin arms
- Nose pads
- Tinted lenses
Style Number/Barcode: 07008-0958
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Abstract Art Satin Wide Leg Pants
Abstract art you can wear! Slay an art gallery opening in these fierce satin pants featuring a high-rise elasticized waistband, front pleating, and a wide-leg silhouette. Complete the look in the matching top.
Shop Matching Top: Abstract Art Satin Convertible Top
Fit & Features
- High-rise elasticized waistband
- Front pleating
- Wide-leg silhouette
- Abstract print, satin fabric
- Runs true to size
Style Number/Barcode: 06402-0414
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simply Elevated One-Shoulder Bodysuit
This simply elevated sleeveless bodysuit will bring the chic vibes to your casual look. It features a one-shoulder neckline with a single tank shoulder strap, a side cutout at the waist with an adjustable drawstring, a thong bottom, and a form-hugging fit. Style with high-rise jeans.
Fit & Features
- Sleeveless one-shoulder neckline
- Tank shoulder strap
- Side cutout at the waist, adjustable drawstring
- Thong bottom, dual snap button closure
- Form-hugging fit
- Brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4400
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Under The Palms Halter Skater Dress
Get ready to relax under the palms in this adorable printed skater dress. It features a sleeveless V-neckline with halter straps, side cutouts leading to a strappy banded back design, a smocked high waist, and a flowy skater skirt silhouette. The lightweight gauze fabric features an all-over tropical palm leaf print. Style with espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Halter spaghetti straps, tie at the back of the neck
- Side cutouts, strappy banded back design, tie closure
- Smocked high waist, flowy skater skirt
- Tropical palm leaf print
- Gauze fabric, knit skirt lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4499
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise Cove Slit Maxi Skirt
Enter paradise cove in true vacay style! This tropical maxi skirt features a high-rise waist, front high-cut slit, and a trendy palm print on stretchy lined fabric. Complete the look in the matching top and sunglasses.
Shop Matching Top: Paradise Cove Cowl Neck Crop Top
Fit & Features
- High rise waist
- Front high-cut slit
- Maxi-length hem
- Tropical palm-print
- Stretchy lined knit fabric
- Runs true to size
Style Number/Barcode: 06501-0659
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paradise Cove Cowl Neck Crop Top
Enter paradise cove in true vacay style! This tropical tank top features a sleeveless, cowl neck, sleek bungee spaghetti straps, cropped hem, and a trendy palm print on stretchy lined fabric. Complete the look in the matching bottoms and sunglasses.
Shop Matching Bottoms: Paradise Cove Slit Maxi Skirt
Fit & Features
- Sleeveless, cowl neck, bungee spaghetti straps
- Cropped hem
- Tropical palm-print
- Stretchy lined knit fabric
- Runs true to size
Style Number/Barcode: 06001-4262
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elise Destructed Denim Mini Skirt by Windsor Denim
The Elise destructed denim skirt will elevate all of your casual 'fits. The cute mini skirt by Windsor Denim features a high-rise waist, subtle distressing, a short, form-hugging fit, and a trendy frayed hem. The dark wash denim fabric offers a moderate stretch. Style with a crop top and mules.
Fit & Features
- High-rise waist
- Subtle distressing
- Five-pocket and belt loop design, front button, hidden zipper closure
- Mini-length, form-hugging fit
- Frayed hem
- Dark wash denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0059
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance