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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Can't Go Wrong Crochet Knit Shorts
You can't go wrong with these crochet knit shorts perfect for a sunny day out on a weekend or vacation!
Fit & Features
- Crochet knit fabric, sheer design
- Low-rise drawstring waist
- Fitted hem
- Runs true to size
Style Number/Barcode: 06503-000026
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Leaf Fringe Hoop Earrings
These dainty detailed hoops will bring that boho-chic glam! They feature a textured hoop with leaf-shaped charms in a dangling fringe design. Style with a layered necklace set.
Fit & Features
- Textured hoop
- Leaf-shaped charms, fringe design
- Rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1560
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Impressed Satin Pleated Maxi Skirt
You'll always be dressed to impress in this satin pleated maxi skirt featuring an elasticized high-rise waist, slim bodycon silhouette, and a center front side ruched seam atop a flirty slit. Style with the matching top for a night of dinner and dancing!
Shop Matching Top: Always Impressed Satin Pleated Crop Top
Fit & Features
- High-rise elasticized waist
- Slim, bodycon silhouette
- Center front side ruched seam, high slit
- Maxi-length hem
- Satin pleated fabric, backside lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06501-0793
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Always Impressed Satin Pleated Crop Top
You'll always be dressed to impress in this satin pleated top featuring a sleeveless V-neck, wide straps, a center-ruched bust seam, and a fitted crop hem. Style with the matching skirt for a night of dinner and dancing!
Shop Matching Bottoms: Always Impressed Satin Pleated Maxi Skirt
Fit & Features
- Sleeveless V-neck
- Wide straps
- Center-ruched bust seam
- Fitted crop hem
- Satin pleated fabric, bust lining
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4716
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mixing It Up Twist Sweater Top
Mix up your everyday style in this flirty sweater crop top featuring a sleeveless, sweetheart neck, tank-style straps, and a twisted bodice on stretchy and soft rib-knit fabric. Complete the look in high-rise skinny jeans for a brunch.
Fit & Features
- Sleeveless, sweetheart neck, tank-style straps
- Twisted bodice
- Cropped hem
- Soft and stretchy
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1310
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Totally In Fringe Rhinestone Denim Shorts
You can be found in these denim shorts all season long! They feature a flattering high-rise waist, cascading rhinestone fringe along the front, and a cut-off style hem on premium non-stretch denim fabric. Complete the look in a flirty crop top and cowboy boots for a festival!
Fit & Features
- High-rise waist
- Cascading front rhinestone fringe
- Cut-off style hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium non-stretch denim fabric
- Runs true to size
Style Number/Barcode: 06603-0346
Category Name: Vacation Looks
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On The Verge Chiffon A-Line Midi Dress
You'll be on the verge of a stylish breakthrough with the addition of this chiffon midi dress to your fashion closet! Effortless and breezy, this dress features a sleeveless v-neckline, halter spaghetti straps, a lace-up open back that lets you customize the fit, and an asymmetrical hem with a flirty slit. Complete the look with stiletto heels and a bracelet!
Fit & Features
- Sleeveless v-neckline
- Halter spaghetti straps
- Lace-up open back
- A-line silhouette
- Asymmetrical midi-length hem, slit accent
- Chiffon fabric, stretchy knit lining
- Fits true to size
Style Number/Barcode: 05102-4905
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Diva Rhinestone Denim Block Heels
You'll be a total trendy diva with these sparkly rhinestone denim heels! They feature an open square-shaped toe, a wide toe strap, a thin adjustable ankle strap, a closed back, a block heel, and all-over rhinestones on the denim material. Style with a mini handbag.
Fit & Features
- Open square-shaped toe
- Wide toe strap
- Thin adjustable ankle strap, buckle detail, closed back
- Block heel
- Rhinestone embellishments
- Denim material
- Runs true to size
Style Number/Barcode: 07401-4163
Category Name: Vacation Looks
Price: $14.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Festivities Chunky Platform Heels
These bold platform heels were made for fun weekend festivities! They feature an open almond-shaped toe, dual braided straps, a chunky platform sole, and an ultra-tall block heel that will level up your look. Style with a sleek clutch for drinks with the girls!
Fit & Features
- Open almond-shaped toe
- Dual braided straps
- Open back
- Chunky platform sole
- Ultra-tall block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4286
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Rhinestone Buckle-Strap Sandals
Casual with a glam touch, these buckle-strap sandals are a trendy style for the summer season. They feature a round toe, a two-strap design with adjustable buckles, sparkling rhinestone embellishments, an open back for easy on-and-off styling, and a flat sole. Pair with hoop earrings.
Fit & Features
- Round toe
- Two-strap design, adjustable buckles
- Mini rhinestones
- Open back
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1137
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cross Paths Strappy Slide Sandals
Let these faux leather sandals cross your path! Perfect for casual days out or somewhere by the water, these sandals feature an on-trend square toe, asymmetrical thin strappy design, a flat sole, and a slide-on-and-off styling. Complete the look with chic jewelry.
Fit & Features
- Square toe
- Asymmetrical thin strappy design
- Flat sole
- Slide-on-and-off styling
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1090
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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You Better Work Lace-Up Crop Top
Work it out girl with a crop top that slays! The crop top features a sleeveless square neckline, tank shoulder straps, a lace-up back, and a cropped hem. The top is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with high waist shorts and mules.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Lace-up back
- Cropped hem
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1684
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Robyn High-Rise Crop Flare Jeans By Windsor Denim
Kick up your style in the must-have Robyn jeans by Windsor denim perfect for adding to your spring-to-summer lineup! They feature a flattering high-rise waist, hip-hugging fit, distressed knee accent, and a flare crop raw hem on premium white denim with a moderate stretch. Complete the look in a trendy crop top and wedges for a pool party!
Fit & Features
- High-rise waist, hip-hugging fit
- Distressed knee accent
- Flare cropped raw hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Premium white denim, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0413
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Language Of Romance Lace Babydoll Dress
This lace babydoll dress speaks your language for romance! Let this short dress sweep you off your feet for wedding showers, graduations, or birthday brunches! It features three-quarter-length puff sleeves, a square neck, a stretchy smocked back, and an empire waist seam that flares out into the flowy hem. Complete the look in new sandals and a clutch!
Fit & Features
- Three-quarter-length puff sleeves
- Square neck
- Stretchy smocked back
- Empire waist, fit and flare silhouette
- Flowy short-length hem
- Lace overlay, chiffon lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4973
Category Name: Vacation Looks
Price: $5.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dazzle Me Rhinestone Square Toe Sandals
Bring a dazzling aura in these square toe sandals embellished with sparkling rhinestones, perfect for day or night.
Fit & Features
- Square toe
- Rhinestone-embellished strap
- Fat sole with rhinestone-embellished trim
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-000034
Category Name: Vacation Looks
Price: $20.90
Availability: Out of Stock
Product Badge:- Ships Free
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Loveliest Of Them All Chiffon Skater Dress
You'll be the loveliest of them all in this chiffon skater dress - a stunning option for bridal showers, graduations, or dressy parties! The short dress features a sleeveless plunge V-neckline along the front and back, a ruched high waist, and a flowy fit and flare silhouette. Complete the look with rhinestone block heels for some shine!
Fit & Features
- Sleeveless plunge front and back V-neckline
- Back zipper and hook-eye closure
- Ruched high waist
- Skater, fit and flare silhouette
- Flowy short-length hem
- Airy chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2160
Category Name: Vacation Looks
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lovely In Floral Lace Trim Midi Dress
You'll be a sight for sore eyes in this lovely floral midi dress - a flirty option for garden weddings, dressy birthdays, and day dates! The sleeveless dress features a sweetheart neckline with a romantic eyelash lace trim, adjustable spaghetti straps, a curve-hugging bodice, and a slit accent along the flowy hem. Complete the look with earrings and heels.
Fit & Features
- Sleeveless sweetheart neckline, padded wired bust, eyelash lace trim
- Adjustable spaghetti straps, back zipper, hook and eye closure
- Curve-hugging bodice
- Slit accent, midi-length hem, A-line silhouette
- Delicate floral print
- Sheer woven fabric, full lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2228
Category Name: Vacation Looks
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet As Me Eyelet Lace Skater Dress
This eyelet lace dress is sure to be the sweetest style in your closet! It features puff short sleeves, a sweetheart neck with a bust tie, ruched bust, and a fit and flare skater silhouette. Complete the look with a ring set and heels.
Fit & Features
- Puff short sleeves
- Sweetheart neck, bust tie
- Ruched bust
- Fit and flare skater silhouette
- Short-length hem
- Eyelet lace, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4924
Category Name: Vacation Looks
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Palms Tropical One-Shoulder Dress
This tropical mini dress will put you in vacay mode! Flaunt some skin in this sleeveless one-shoulder dress featuring a sleek bungee spaghetti strap, side ruched seams to accentuate your curves, and a bodycon fit. The dress is designed with a palm leaf print on stretchy knit-lined fabric. Complete your getaway look in platform wedges.
Fit & Features
- Sleeveless one-shoulder neckline
- Bungee spaghetti strap
- Side ruched seams
- Bodycon fit, mini-length hem
- Palm leaf print
- Lined stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4956
Category Name: Vacation Looks
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wild Zebra Side Tie Mini Skirt
Why blend in when you can stand out! Stay ahead of the trend in this zebra print mini skirt featuring a high-rise waist, form-fitting silhouette, and dual side ties along the mini hem. Complete the look in the matching top.
Shop The Matching Top: Wild Zebra Crop Tank Top
Fit & Features
- High rise waist
- Form-fitting silhouette
- Dual side ties
- Zebra print
- Knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0642
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wild Zebra Crop Tank Top
Why blend in when you can stand out! Stay ahead of the trend in this zebra print tank crop top featuring a v-neck, spaghetti straps, ruched seams along the bust, and a cropped hem. Complete the look in the matching skirt.
Shop The Matching Skirt: Wild Zebra Side Tie Mini Skirt
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Ruched seam along the bust
- Cropped hem
- Zebra print
- Knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4122
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cloud Cruisin’ Oval Frame Sunglasses
These trendy oval sunglasses serve retro realness with a sleek plastic frame—perfect for iced lattes, low-effort fits, and avoiding eye contact with your ex.
Fit & Features
- Smooth plastic oval frames
- Subtle curve with mid-coverage lenses
- Classic Y2K-inspired silhouette
Style Number/Barcode: 07008-000049
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Made You Look Open Back Denim Jumpsuit
Make every look back at you in this stunning denim jumpsuit perfect for a weekend trip or hitting up the country bar! It features a sleeveless square neck, tank-style straps, exposed front zipper closure, a backless design with a tie closure, a hip-hugging fit, and a flared raw hem. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless square neck, tank-style straps
- Exposed front zipper closure
- Backless design with tie closure
- Hip-hugging fit, pockets
- Flared raw hem
- Medium wash denim, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0407
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Standout In Style Swirl Print Maxi Skirt
Standout in this stylish swirl print maxi skirt on vacation or sitting poolside at a party! The skirt features a flattering high-rise waist, a curve-hugging silhouette, and a front ruched drawstring atop a flirty high slit along the maxi hem. Complete the look in a basic tank top and sandals!
Fit & Features
- High-rise waist
- Curve-hugging silhouette
- Front ruched drawstring
- High front slit, maxi-length hem
- Swirl print design
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06501-0830
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance