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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Yacht Party Sheer Mesh Duster
Look like you're ready for a luxe yacht party with this fab sheer mesh duster! It features long fitted sleeves, an open front, a flowy, maxi-length silhouette, and an all-over tropical palm leaf print. Layer this breezy lightweight duster over your fave bikini and top off the look with a trendy floppy hat.
Fit & Features
- Long fitted sleeves
- Open front
- Maxi-length silhouette
- Flowy fit
- Palm leaf print
- Sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0316
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Stripe Halter Linen Jumpsuit
Dare to show some flirty peeks of skin! This linen striped jumpsuit features a halter neckline with tie closure, a cinched bust, cutout accents, a high waist, and a wide-leg silhouette. Complete the look with a handbag for a beachside lunch.
Fit & Features
- Sleeveless, halter neckline, tie closure
- Cinched bust, cutout accents
- High waist, back smocked panel
- Wide-leg silhouette
- Striped print linen fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0615
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Desert Stroll Tie-Front Top
Snap the perfect pics in this boho top for your next trip to Joshua tree! It features long bell sleeves, a plunge v-neckline, a tie-front hem, and a border print on gauze woven fabric. Complete the look in a lace bralette.
Fit & Features
- Long bell sleeves
- Plunge v-neckline
- Tie-front hem
- Border print
- Gauze woven fabric
- Fits true to size
Style Number/Barcode: 06204-1339
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Charmed Linen Tie Front Top
Channel major charm in this linen tie-front top featuring short puff sleeves, an open-front design, and a cropped hem. Complete the look with a lace bralette and jeans.
Fit & Features
- Short puff sleeves
- Open-front design
- Tie front closure
- Cropped hem
- Washed linen fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1277
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Valerie Tiered Floral Printed Dress
Special Occasion
Get an absolutely gorgeous look for graduations, weddings, or any special summer event in the Valerie floral printed dress! She features a sleeveless subtle sweetheart neckline with a tie-front detail, adjustable spaghetti straps for a customized fit, a high waist seam, and a floor-length hem with a tiered design and a flowy silhouette. The lightweight gauze fabric showcases an all-over tropical floral print. Complete the look with cute wedges.
Fit & Features
- Sleeveless sweetheart neckline, tie-front detail, ruched bust
- Strapless or adhesive bra recommended
- Adjustable spaghetti straps, smocked back
- High waist seam, floor-length hem with a tiered, layered design
- Tropical floral print
- Gauze fabric, woven lining
- Flowy silhouette, minimal stretch
- Runs true to size
Style Number/Barcode: 05002-2116
Category Name: Vacation Looks
Price: $19.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Shift In Seasons Floral Skater Dress
The sun rises with the shifting seasons and this flirty floral skater dress is ready to make an appearance! Featuring a sleeveless, square neckline, spaghetti straps, a smocked bodice, and a flowy, short skirt. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless, square neckline, spaghetti straps
- Smocked bodice
- Skater short silhouette
- Floral print
- Swiss dot chiffon, inner knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-1507
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take Flight Ombre Aviators
Soar to new fashion heights rocking these aviators for a cool-girl vibe. They feature a sleek metal frame, an aviator design, and an ombre lens on sleek metal arms. Complete the look in a crop jacket and jeans.
Fit & Features
- Sleek metal frame
- Aviator design
- Ombre lens
- Comfortable rubber nose pads
- Metal arms
Style Number/Barcode: 07008-0918
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Flutter Sleeve Floral Duster
Layer on this breezy floral chiffon duster for an effortlessly pretty look! It features short flutter sleeves, a V-neckline, a button-front closure, and an airy, high-low hem. Style this duster with cute espadrille wedges.
Fit & Features
- Short flutter sleeves
- V-neckline
- Button-front closure
- Smocked panel at the back
- Flowy, high-low hem
- Sheer chiffon fabric, floral print, no stretch
- Runs true to size
Style Number/Barcode: 06204-1288
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Snake Sass Triangle Bikini Top
Sass it up in this snake print bikini top! It features triangle cups, removable padding, spaghetti straps, and clear straps. Complete the look in the matching bikini bottoms.
Shop Matching Bikini Bottoms: Snake Sass Bikini Bottoms
Fit & Features
- Triangle cups
- Removable padding
- Spaghetti straps, clear straps
- Snake print
- Lined, moderate stretch
- Runs true to size
Style Number/Barcode: 07104-0663
Category Name: Vacation Looks
Price: $4.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Alluring Beauty Halter Crop Top
Showcase your alluring beauty in this on-trend crop top. It features a sleeveless halter neckline with a cross-front design, a center cutout at the bust, an open back, and a majorly cropped fit. Style with the matching midi skirt and heels for a girl's night out.
Shop Matching Bottoms: Alluring Beauty High Slit Midi Skirt
Fit & Features
- Sleeveless halter neckline, cross-front design
- Center cutout at the bust, structured underwire
- Open back
- Cropped
- Lined ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4375
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Petals and Plans Floral Lace-Up Maxi Dress
For date nights, rooftop drinks, or weddings, this floral maxi dress is perfect for every event! The curve-hugging fit, flirty slit, and open lace-up back effortlessly flatters your figure and makes heads turn.
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Square neckline
- Spaghetti straps
- Lace-up open back
- High front slit
- Curve-hugging fit, maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-4160
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfectly Ripe Peplum Tank Top
This peplum tank top is perfectly in-season! Bare your shoulders in this adorable sleeveless, scoop neck sweater featuring a flirty ruffled hem on stretchy knit fabric. Complete the look in high-rise jeans for a cute coffee run.
Fit & Features
- Sleeveless, scoop neck, tank straps
- Ruffled hem
- Sweater knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1320
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Breeze Crochet Maxi Dress
Look and feel like a daydream in this boho maxi dress designed in a breezy, silhouette featuring a sleeveless, crochet lace v-neck bodice, spaghetti straps, and a sultry open-back with a tie closure that leads to the flowy long hem. Complete the look in strappy sandals.
Fit & Features
- Sleeveless, crochet lace v-neck bodice, spaghetti straps
- Open-back, tie closure
- Flowy maxi silhouette
- Long-length hem
- Partially lined woven fabric
- Fits true to size
Style Number/Barcode: 05102-4449
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Got Greens Mesh Money Print Tee
Got greens? Flaunt your money moves in this sheer mesh crew tee featuring cap sleeves, a fitted bodice, crop hem, and hundred dollar print. Complete the look in a bralette and sunglasses.
Fit & Features
- Cap sleeves
- Crew neck
- Money/hundred dollar print
- Fitted bodice
- Crop hem
- Sheer mesh fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06001-4137
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Diva Cutout Snake Bodysuit
Make a bold statement with a bodysuit that raises the heat! The bodysuit features a snake pattern, sleeveless crew neckline, a sexy cutout with a lace-up bodice, and a thong bottom with dual snap button closure. The bodysuit is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with high waist pants.
Fit & Features
- Snake print
- Sleeveless crew neckline
- Crew neckline
- Cutout with lace-up accent
- Thong bottom, dual snap button closure
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3978
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Perfect Basic Knit Crop Top
This ribbed knit crop top is the perfect basic to style up for every day! It features a V-neckline, short sleeves, a wrap-front design leading to a tie-back closure, and a cropped, form-hugging fit. Style with distressed denim shorts and simple hoop earrings.
Fit & Features
- V-neckline, short sleeves
- Wrap-front design
- Tie-back closure
- Crop fitted hem
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1173
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Weekend Mood Wide-Leg Pants
Get ready for a relaxing weekend in these adorable woven pants. They feature a high-rise paper bag waist, a tie-front detail, pleating, and a flowy, wide-leg fit. Complete your getaway look with the matching tie-front top and cute espadrille sandals.
Shop Matching Top: Weekend Mood Tie-Front Top
Fit & Features
- High-rise elasticized paper bag waist
- Tie-front detail
- Pleating
- Wide-leg fit
- Flowy silhouette
- Lightweight gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0625
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Weekend Mood Tie-Front Top
Get ready for a relaxing weekend in this adorable woven tie-front top. It features short flutter sleeves, a V-neckline, a tie-front design, and a cropped fit. Complete your getaway look with the matching wide-leg pants and cute espadrille sandals.
Shop Matching Bottoms: Weekend Mood Wide-Leg Pants
Fit & Features
- Short flutter sleeves
- V-neckline
- Tie-front
- Cropped
- Lightweight gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1229
Category Name: Vacation Looks
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Art Deco Choker Set
Create an artsy vibe with this choker four-piece set featuring one diamond coin charm, one rhinestone, and two geo chain-link layers each with lobster clasp closure. Complete the look in a chic dress for date night.
Fit & Features
- Four-piece choker set
- One diamond coin charm
- One rhinestone
- Two geo chain-link layers
- Lobster clasp closure
Style Number/Barcode: 07002-1154
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Out Of Water Mesh V-Neck Coverup
Take a break from the water and slip on this chic mesh coverup featuring long bell sleeves, a v-neck, and a bodycon silhouette with a side ruched seam and tie-back closure. Complete the look in a glittery swim set and shades.
Fit & Features
- Long bell sleeves, v-neck
- Bodycon silhouette
- Side ruched seam
- Tie-back closure
- Mini-length hem
- Sheer mesh fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06001-4188
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ally High-Rise Denim Mini Skirt by Windsor Denim
Style up your everyday casual looks with the Ally denim mini skirt by Windsor Denim! Featuring a high-rise waist, destructed detailing, and a mini-length frayed hem, this jean skirt is a cute wardrobe staple. It is composed of a light wash denim fabric that offers a moderate stretch. Pair with your fave crop tops.
Fit & Features
- High-rise waist
- Distressed accents, fitted silhouette
- Mini-length, frayed hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Light wash denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06601-0051
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Poolside Vibe Mesh Coverup
Showcase only chic vibes as you lounge poolside in this sultry mesh coverup dress! It features a sleeveless scoop neckline, spaghetti straps, ruching down one side, and a fitted maxi-length silhouette with a high side slit. The sheer mesh fabric offers a moderate stretch and an airy, lightweight feel. Style this coverup over your fave bikini with cat-eye sunglasses.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Ruched side detailing, high side slit
- Fitted maxi-length silhouette
- Sheer mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4187
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All It Takes Linen Halter Jumpsuit
This halter linen jumpsuit is all it takes to look chic on the go! It features a sleeveless, plunge v-neckline, a front hoop inset, a form-fitting silhouette, and an open-back with dual tie closures. Complete your vacay look in sleek hoop earrings.
Fit & Features
- Sleeveless, halter plunge v-neckline
- Front hoop inset
- Form-fitting silhouette
- Open-back, dual tie closures, zipper closure
- Partially lined linen fabric
- Fits true to size
Style Number/Barcode: 06302-0622
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Remy High-Rise Cutoff Denim Shorts by Windsor Denim
Every girl needs that classic pair of cutoff jean shorts! The Remy high-rise shorts by Windsor denim are perfect for creating cute and casual summer 'fits. They feature subtle distressing, an on-trend frayed cutoff hem, and a form-hugging fit. The medium wash denim fabric offers a moderate stretch for comfortable wear. Style with your fave graphic tee.
Fit & Features
- High-rise waist
- Destructed detailing, frayed cutoff hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Medium wash denim fabric, moderate stretch
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06603-0233
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance