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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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: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L, XL
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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: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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
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Talk About Breezy Chiffon Crop Top
Styling this chiffon crop top will be such a breeze! The top features peasant sleeves with ruffled cuffs, pleated shoulder details, a ruched sweetheart neckline, a built-in padded bust with overlay, and a back zipper and hook-eye closure. Complete the look in best-selling skinny jeans.
Fit & Features
- Peasant sleeves, ruffled cuffs, pleated shoulders
- Ruched sweetheart neckline
- Built-in padded bust with an overlay
- Cropped hem
- Back zipper and hook-eye closure
- Lined chiffon crepe non-stretch fabric
- Fits true to size
Style Number/Barcode: 06003-1962
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wrapped In Chic Vibes Satin Maxi Skirt
Get wrapped in chic vibes in this sleek satin maxi skirt! It features a high-rise waist with ruched detailing, a faux wrap-front design creating a high front slit, a maxi-length hem that hits right above the ankle, and a curve-hugging silhouette. Style with a cropped bustier and clear heels.
Fit & Features
- High-rise waist, ruching
- Hidden back zipper closure
- Faux wrap-front design, high front slit
- Maxi-length hem
- Curve-hugging fit
- Woven satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06401-0562
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Strides Rhinestone Strap Heels
Take your next glamorous strides in these luxe faux leather heels featuring a sleek square toe, dual PVC straps with rhinestone embellishment, and a lucite stiletto heel with a flat geo-shaped bottom. The heels showcase a chic metallic sheen. Style with stunning jewelry set to complete the dressy look!
Fit & Features
- Square toe
- Dual PVC straps, rhinestone embellishments
- Lucite stiletto heel, flat geo-shaped bottom
- Metallic sheen
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4164
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Just A Peek Crew Neck Keyhole Top
Attract all the attention by showing off just a peek of your skin! This elevated basic crop top features fitted long sleeves, a crew neck with hidden hook and eye closures, and a keyhole cutout accent atop the surplice bodice on stretchy rib-knit fabric. Style with straight-leg jeans to complete your trendy look!
Fit & Features
- Fitted long sleeves
- Crew neck
- Hidden front hook and eye closures
- Keyhole cutout accent
- Surplice bodice, cropped hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1524
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rendezvous In Satin Slip Midi Dress
Have a chic rendezvous in this satin slip midi dress featuring a sleeveless V-neck, bungee spaghetti straps, a fitted a-line silhouette, and a sultry front slit along the hem. The dress is composed of smooth, non-stretch satin fabric. Complete the look in lace-up stiletto heels.
Fit & Features
- Sleeveless V-neck
- Bungee spaghetti straps
- Fitted a-line silhouette
- Front slit
- Midi-length hem
- Non-stretch woven satin fabric
- Runs true to size
Style Number/Barcode: 05101-2383
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Meant To Be Lace Up Corset Top
This corset top is meant to be in your lineup this season! Add a sultry touch to your everyday look in this strapless top featuring flexible boning inserts along the cropped bodice and an eye-catching lace-up back for a customized fit. Style with wide-leg pants for cocktail hour!
Fit & Features
- Strapless and sleeveless
- Flexible boning inserts
- Cropped hem
- Lace-up back, tie closure
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-2179
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Perfectly Pleated Cuffed Trouser Pants
Achieve a chic, polished look with these perfectly pleated cuffed trouser pants. They feature a high-rise waist, belt loops, front pockets, crisp pleated detailing near the waist, a straight-leg fit, and a cuffed hem. Elevate the look of these smooth woven pants with a cropped blouse and clear mules.
Fit & Features
- High-rise waist, belt loops
- Hidden front zipper, button, and hook and bar closures
- Front pockets
- Pleating
- Straight-leg fit, cuffed hem
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-0506
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free