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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Diva Vibes Ruched Rhinestone Sandals
Live your best life and give off diva vibes in these glam rhinestone sandals! They feature an open square toe, a ruched toe strap with mini rhinestone embellishments, a thin adjustable heel and ankle strap, and a flat sole. Style with a mini dress and hoop earrings.
Fit & Features
- Open square toe
- Ruched toe strap
- Mini rhinestones
- Thin adjustable heel and ankle strap
- Flat sole
- Faux suede material, faux leather insole
- Runs true to size
Style Number/Barcode: 07404-1106
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stay Trendy Strappy Platform Sandals
These strappy platform sandals will keep your casual 'fits trendy and cute! They feature an open round toe, a double-banded strap design, an adjustable heel strap, and a platform sole. Style with a cropped denim jacket.
Fit & Features
- Open round toe
- Double-banded strap design
- Adjustable heel strap, buckle detail
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1107
Category Name: Vacation Looks
Price: $12.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Follow Your Heart Hoop Earrings
Follow your heart and add some glamour to your look with these adorable hoop earrings! They feature a layered design of three heart-shaped metal outlines with textured detailing. Style with a flirty cropped blouse and a satin midi skirt.
Fit & Features
- Layered design
- Three heart-shaped metal outlines
- Textured detailing
- Omega closure, rubber stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1472
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Edgy Faux Pearl Chain Layer Necklace
Pretty and edgy! This layered necklace is sure to give your outfit an eye-catching detail. It features three layers with one faux pearl and chain layer, one statement chain link layer, and one snake chain layer each with lobster clasp closures. Complete the look in a ring set.
Fit & Features
- Three layered necklace
- One faux pearl and chain layer
- One statement chain link layer
- One snake chain layer
- Each has lobster clasp closures
Style Number/Barcode: 07002-1374
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Total Trendsetter Chunky Platform Sandals
Show off your trendsetting style in these of-the-moment chunky platform sandals. They feature an open almond-shaped toe, a wide banded toe strap with a cushioned fabric for comfort, an open back for easy on-and-off styling, and a platform and thick low block heel with a lug sole. Style these faux leather sandals with hoop earrings.
Fit & Features
- Open almond-shaped toe
- Wide banded toe strap, cushioned fabric
- Open back
- Platform, thick low block heel, lug sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1109
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bohemian Chic Strappy Sandals
These on-trend strappy sandals will give off major bohemian chic vibes! They feature a round toe with a criss-cross strappy design, wrap-around adjustable heel and ankle straps, and a flat sole with a subtle cushioned insole. Style with a flowy printed midi dress.
Fit & Features
- Round toe
- Criss-cross strappy design
- Wrap-around adjustable heel and ankle straps, buckle detail
- Flat sole, subtle cushioned insole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1111
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Daisy Floral Print Sandals
Oh-so-darling, these daisy floral print sandals will create a cute springtime look. They feature a round toe, a wide woven strap with a bow design and an adorable daisy print floral pattern, an open back for easy on-and-off styling, and a flat sole with an espadrille trim. Style with a casual dress.
Fit & Features
- Round toe
- Wide woven strap, bow design
- Daisy print floral pattern
- Open back
- Flat sole, espadrille trim
- Faux leather insole
- Runs true to size
Style Number/Barcode: 07404-1104
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bloom With Grace Lace-Up Maxi Dress
This floral mesh maxi stuns with a draped cowl neckline and lace-up back that’s perfect for making heads turn at weddings, formals, or any RSVP that matters.
Fit & Features
- Floral print, mesh fabric, stretchy knit lining
- Cowl neckline
- Spaghetti straps
- Lace-up back
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000187
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pour It Up Mesh Ruched Mini Dress
Pour yourself a glass of this mesh mini dress perfect for a bachelorette babe! Featuring a sleeveless sweetheart neck, tank-style straps, a lightly padded bust, side and back ruched seams, and a curve-hugging silhouette. Complete the look in statement heels.
Fit & Features
- Sleeveless sweetheart neck, tank-style straps
- Lightly padded bust
- Back zipper and hook-eye closure
- Side and back ruched seams
- Bodycon silhouette, mini-length hem
- Lined mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05103-4725
Category Name: Vacation Looks
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Romance Long Sleeve Lace Mini Dress
Show off sweet romantic vibes in this stunning lace mini dress. It features a sweetheart neckline, a center keyhole cutout at the waist, sheer long fitted sleeves, a sheer back design, and a mini-length hem with a curve-hugging silhouette. The partially lined lace fabric offers a moderate stretch. Style with clear heels.
Fit & Features
- Sweetheart neckline
- Center keyhole cutout at the waist
- Sheer long fitted sleeves
- Sheer back design
- Mini-length hem, curve-hugging fit
- Sheer lace fabric, partial knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2157
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Winged Spirit Butterfly Hair Pins
Own your spirit for all things with wings! These charming three-pack butterfly hairpins feature a filigree design with shimmering embellishments and partial translucent layered wings. Complete the look in a sassy satin corset for a dinner date!
Fit & Features
- Three-pack butterfly hair pins
- FIligree design
- Shimmering embellishments
- Partial translucent layered wings
Style Number/Barcode: 07006-0371
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Luxe Lounge Rhinestone Strap Slides
Have yourself a luxe lounge look slipping into these slides featuring a round toe, comfort foam sole, and an embellished rhinestone wide strap. Style with a cozy crop jacket to complete the look!
Fit & Features
- Round toe
- Comfort foam sole
- Embellished rhinestone wide strap
- Slip-on and off styling
- Runs true to size
Style Number/Barcode: 07404-1112
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Allure Mesh Crop Bustier
You'll be all sorts of alluring in this floral mesh bustier perfect for adding a touch of romance to your closet! It features a sleeveless sweetheart neckline, tank-style straps, an underwire bust, side ruched seams, and a cropped hem. The top is composed of lined mesh fabric along the hem and back with minimal stretch and a blooming floral print. Complete the look in an oversized blazer and jeans.
Fit & Features
- Sleeveless sweetheart neckline
- Tank-style straps
- Underwire bust
- Side ruched seams, cropped hem
- Back zipper and hook-eye closure
- Blooming floral print, lined mesh fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4588
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glamorous Allure Ruched Lace Maxi Skirt
This chic lace maxi skirt will give you a luxe glamorous allure! It features a high-rise waist with a hip-hugging fit, front ruching leading to a sultry thigh-high front slit, and a maxi-length hem with an A-line silhouette. The lined lace fabric features a dainty floral pattern. Style with a corset top and strappy stilettos.
Fit & Features
- High-rise elasticized waist, hip-hugging fit
- Front ruching, high front slit
- Maxi-length hem, A-line silhouette
- Sheer lace fabric, floral pattern, full knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0815
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Downright Darling Lace V-Neck Dress
You'll be downright darling in this flirty lace short dress perfect for day dates and brunch! It features a sleeveless v-neckline, ruffled trim adjustable spaghetti straps, a sheer trim along the bodice, an a-line silhouette, and a ruffled tiered hem. Complete the look in platform block heels.
Fit & Features
- Sleeveless v-neckline
- Ruffled trim adjustable spaghetti straps
- Back zipper closure, sheer bodice trim
- A-line silhouette
- Ruffled tiered short-length hem
- Lined lace fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 05101-2300
Category Name: Vacation Looks
Price: $39.90
Availability: Out of Stock
Product Badge:- Sale
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Tie Dye Over Bodycon Mini Dress
You'll tie-dye over this casual mini dress to add some color to your closet for warmer seasons ahead! It features a square neck, bungee spaghetti straps, and side ruched seams that accentuate your curves along the bodycon silhouette. The dress is composed of stretchy mesh fabric with a sewn-in knit lining. Complete the look in a cropped denim jacket and sneakers.
Fit & Features
- Sleeveless, square neck
- Bungee spaghetti straps
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Tie-dye pattern, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4931
Category Name: Vacation Looks
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Extra Flair Floral Skater Dress
You'll be a darling delight in this short skater dress perfect for parties and ceremonies! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is composed of a floral burnout woven fabric with a chiffon lining and no stretch. Style with earrings and a choker to complete the look!
Fit & Features
- Three-quarter-length puff sleeves
- Square neck
- Smocked back
- Fit and flare skater silhouette
- Short-length hem
- Floral burnout woven fabric, chiffon lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2211
Category Name: Vacation Looks
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swept Away Floral Chiffon Maxi Dress
Get swept away in this dreamy floral chiffon maxi dress to serve romantic vibes at every brunch or baby shower! The dress features long peasant sleeves with ruffle trim along the shoulders, a sweetheart neckline, a lightly padded bust, a smocked back, and an A-line silhouette with a sultry side slit. The dress is composed of an airy chiffon fabric with a blooming floral print and a woven lining. Complete the look in strappy heels.
Fit & Features
- Long peasant sleeves, ruffle trim
- Sweetheart neckline, lightly padded bust
- Smocked back
- A-line silhouette
- Side slit, maxi-length hem
- Blooming floral, non-stretch chiffon fabric, woven lining
- Runs true to size
Style Number/Barcode: 05101-2215
Category Name: Vacation Looks
Price: $5.97 $58.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Into Floral Chiffon Skater Dress
Transition your winter blues into fresh spring florals! This breezy chiffon skater dress is perfect for dressy brunches or engagement parties. It features a surplice V-neckline, sheer peasant sleeves, a tie-back belted waist, and a tiered ruffle short-length hem with an adorable ditsy floral print. Complete the look in lace-up heels.
Fit & Features
- Surplice V-neckline
- Sheer peasant sleeves
- Tie-back belted waist, back zipper and hook-eye closure
- Skater, fit and flare silhouette
- Tiered ruffle short-length hem
- Ditsy floral print, chiffon fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1711
Category Name: Vacation Looks
Price: $5.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trending In Satin High Rise Pants
You'll be trending forever in these essential satin pants perfect for dressing up or down! They feature a high-rise waist, front pleating, and a straight-leg silhouette. The smooth satin-knit fabric offers a moderate stretch. Complete the look in a tie-front top.
Fit & Features
- High-rise elasticized waist
- Front pleating
- Straight-leg silhouette
- Satin-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06502-2281
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Love Swept Chiffon Slit Midi Dress
Let love sweep you off your feet in this breezy chiffon midi dress perfect for a day date! It features adorable short puff sleeves, a sweetheart neckline, a fitted bodice, and a flowy midi-length hem with a flirty slit. Complete the look in platform block heels.
Fit & Features
- Short puff sleeves
- Sweetheart neckline
- Fitted bodice
- Flowy midi-length hem with slit
- Back zipper and hook-eye closure
- Chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-1567
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laid Back Fave Crew Neck Tank Maxi Dress
Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies!
Fit & Features
- Rib-knit stretchy fabric
- Crew neck
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5573
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Put On A Smile Three Pack Bracelet Set
Encourage smiles all around! This three-pack bracelet set features an adorable happy face charm bracelet, one dainty rhinestone bracelet, and one statement chain link bracelet each with a lobster clasp closure. Complete the look in a trendy denim jacket.
Fit & Features
- Three-pack bracelet set
- One happy face charm bracelet
- One dainty rhinestone bracelet
- One statement chain link bracelet
- Each with lobster clasp closure
Style Number/Barcode: 07003-0408
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Babe Cutout Sweater Dress
You'll be such a trendy babe in this adorable cutout sweater dress! Featuring a sleeveless high neckline with a racerback design, a front keyhole cutout at the bust, alluring side cutouts at the waist, a midi-length hem, and a curve-hugging silhouette, this dress is a perfect pick for a night out with the girls. Style with platform heels and a chic handbag.
Fit & Features
- Sleeveless high neckline, racerback design
- Front keyhole cutout at the bust
- Dual side cutouts at the waist
- Midi-length hem, curve-hugging fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1633
Category Name: Vacation Looks
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance