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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Nothing But Edge Coated Romper
Get ready to show off your curves in this edgy coated romper featuring a sleek, sleeveless square neck, spaghetti straps, high waist seam, and flirty waist cutouts leading to the short-length hem. Complete the look in statement earrings for a night on the town.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Back zipper closure
- High waist seam, cutouts
- Form-fitting silhouette
- Short-length hem
- Coated faux leather fabric
- Fits true to size
Style Number/Barcode: 06403-0236
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Playing Favorites Lace-Up Tank Top
Somebody's playing favorites! You'll fall for this floral tank top featuring a sleeveless, scoop neck, tank-style straps, princess seam detail, and a trendy front lace-up with tie closure along the fitted, crop hem. Complete the look in shorts and sandals for a daytime event.
Fit & Features
- Sleeveless, scoop neck, tank-style straps
- Front lace-up, tie closure, princess seam detail
- Fitted crop hem
- Ditsy floral print
- Ribbed-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4285
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Girl On The Run Plaid Crop Blazer
Arrive in style in this plaid crop blazer featuring long sleeves, shoulder pads for a structured fit, lapel collar neckline, and three front hook-eye closures, crafted on woven lined fabric. Complete the look in sleek trouser pants and heels.
Fit & Features
- Long sleeves
- Lapel collar neckline
- Three front hook-eye closures
- Cropped hem
- Buffalo plaid pattern
- Woven lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1461
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make A Wish Starburst Earrings
Make a wish and these starburst earrings will be yours! They feature a linear silhouette, rhinestone insets, and a post-back closure. Complete the look in a matching set for a cute daytime outing.
Fit & Features
- Linear silhouette
- Starbursts design
- Rhinestone insets
- Post-back closure
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07001-1305
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Remy High Rise Distressed Shorts By Windsor Denim
Your new favorite go-to denim shorts that hug just right! The Remy shorts by Windsor Denim feature a flattering, high-rise waist, minimal distressed accents, cool color fading, and a cut-off hem on dark wash denim fabric. Complete the look in a flirty tie-front top and sandals.
Fit & Features
- High-rise waist
- Minimal distressed accents
- Cut-off hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Color fading, dark wash denim, minimal stretch
- Fits true to size
Style Number/Barcode: 06603-0281
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Instinct Slit Midi Skirt
Unleash your fierce-feline side looking so femme in this leopard midi skirt featuring a sleek, high-rise waist, slim fit silhouette, and a sultry front slit accent perfect for showcasing chic mules.
Fit & Features
- High-rise waist
- Slim-fit silhouette
- Front slit accent
- Midi-length hem
- Leopard print
- Crepe knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06501-0671
Category Name: Vacation Looks
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Spot To Go Halter Jumpsuit
You may be at the hottest spot in town but you'll be the one raising the heat in this sleeveless halter jumpsuit featuring a front keyhole cutout, tie-back neck closure, high-rise waist, wide-leg silhouette, and a racerback design with a cutout. Complete the look in statement earrings and a clutch.
Fit & Features
- Sleeveless, halter, tie-back neck closure
- Front keyhole cutout
- Racerback design with cutout
- High-rise waist
- Wide-leg silhouette
- Sleek knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-1079
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Drinks On The Beach Crepe Bra Top
Sipping on cocktails with a beach view! Sultry and chic have never looked so good as on this crepe bra top featuring a sleeveless, plunge V-neck, adjustable spaghetti straps, built-in padded bust, and an elasticized back band with hook-eye closures. Complete the look in the matching top layer.
Shop Matching Top: Drinks On The Beach Crepe Top
Fit & Features
- Sleeveless, plunge V-neck, adjustable spaghetti straps
- Built-in padded bust
- Elasticized back band with hook-eye closures
- Crepe chiffon-lined fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1912
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Nubuck Espadrille Sandals
Effortless and easy to style, these platform sandals are essential for creating all sorts of fab summer looks! They feature a round toe, platform sole with espadrille trim, and nubuck wide strap, and an ankle strap with buckle closure. Complete the look in a breezy floral maxi dress for wine tasting.
Fit & Features
- Round toe
- Platform sole with espadrille trim
- Nubuck wide strap and ankle buckle strap
- Traction bottom design
- Runs true to size
Style Number/Barcode: 07404-1055
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sheerly A Good Time Halter Lace Romper
You're in for a stylishly good time in this sheer lace romper at festivals or concerts! It boasts a sultry open strappy back and a sheer bodice that flaunts your figure.
Fit & Features
- Lace fabric
- Halter V-neckline, spaghetti strap tie
- Open back, spaghetti strap tie
- Sheer fitted bodice
- Ruffled hem
- Runs true to size
Style Number/Barcode: 06503-000048
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Lady Nubuck Cross Sandals
The perfect casual sandals for summertime fun! They feature a round toe, low block heel, criss-cross toe straps, and a buckle ankle strap on nubuck material. Complete the look in a sweater midi dress and denim jacket.
Fit & Features
- Round toe
- Low block heel
- Criss-cross toe strap
- Buckle ankle strap
- Nubuck material
- Runs true to size
Style Number/Barcode: 07404-1054
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Modern Boho Halter Fringe Crop Top
Effortlessly cool and modern, add a bohemian flair to your look with this halter crop top featuring a plunge V-neckline with a surplice accent, tie-back spaghetti straps, a partial open-back, and beaded fringe along the hem. The smooth knit fabric offers plenty of stretch. Complete the look in a fab mini skirt for a night of dancing.
Fit & Features
- Sleeveless, plunge halter V-neckline, surplice accent
- Tie-back spaghetti straps
- Partial open-back
- Beaded fringe
- Cropped hem
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4337
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Drinks On The Beach Crepe Top
Sipping on cocktails with a beach view! Sultry and chic have never looked so good as on this crepe shirt featuring long sleeves with button cuffs, a collared neckline, and a button-down front on a flowy silhouette. Complete the look in the matching bra top.
Shop Matching Bra Top: Drinks On The Beach Crepe Bra Top
Fit & Features
- Long sleeves, button cuffs
- Collared neckline
- Button-down front
- Flowy silhouette
- Crepe chiffon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1913
Category Name: Vacation Looks
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rising Temps Twist Cutout Crop Top
The temps aren't the only thing rising in hotness! This crop top features fitted long sleeves, a crew neck with a ruched side seam, a cutout bodice, and a twisted hem. Complete the look in a fab mini skirt and heels.
Fit & Features
- Fitted long sleeves
- Crew neck, side ruched seam
- Cutout bodice
- Twisted crop hem
- Venezia knit lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4385
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On A Vacay Strapless Tropical Slit Maxi Dress
From sunny vacations to island getaways, this tropical maxi dress is destined to go with you on your next trip!
Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Strapless neckline
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6110
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adored Rhinestone Belly Chain
You'll adore this belly chain for leveling up your fit! Featuring a rhinestone strand with drop accents and a lobster clasp closure. Complete your dressy look in a satin crop top and skirt.
Fit & Features
- Rhinestone strand
- Drop accents
- Lobster clasp closure
Style Number/Barcode: 07002-1255
Category Name: Vacation Looks
Price: $2.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strappy Summer Block Heel Sandals
Step out in this block-heel sandal on a summer night! It features a square toe, low block heel, and a caged front design with lace-up closure on faux leather material. Complete the look in a twirl-worthy skater dress and clutch.
Fit & Features
- Square toe
- Low block heel
- Caged front design
- Lace-up closure
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1049
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Eyes On Style Braid Strap Sandals
All eyes on these stylish sandals featuring an on-trend square toe, dual braid straps, and a low-block heel on faux leather material. Complete the look in a flirty sundress for a lunch date.
Fit & Features
- Square toe
- Dual braid straps
- Low-block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1048
Category Name: Vacation Looks
Price: $12.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stuck On Summer Boho Tube Jumpsuit
Summer calls for breezy boho jumpsuits! It features a strapless neckline, lace-up back, a form-fitting silhouette, and a flared hem. Complete your summer look with statement earrings.
Fit & Features
- Strapless neckline
- Lace-up back design
- Form-fitting silhouette
- Flared hem
- Paisley boho diamond print
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06502-1060
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Take Me On A Getaway Midi Dress
You'll be ready for a fab weekend getaway in this curve-hugging midi dress! It features a sleeveless sweetheart neckline with halter straps, chic waist cutouts, and a midi-length, form-fitting silhouette with a thigh-high side slit. Complete the look with sleek hoop earrings.
Fit & Features
- Sleeveless sweetheart neckline
- Halter spaghetti straps, tie at the back of the neck
- Waist cutouts
- Midi-length, form-fitting silhouette, high side slit
- Textured ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4687
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stack Up Dual Strap Platform Mules
How can high can you stack your style up? These platform mules are major game-changer they feature an almond toe, stacked platform sole, and dual straps on faux leather material. Complete the look in a breezy jumpsuit for a weekend getaway.
Fit & Features
- Almond toe
- Stacked platform sole
- Dual straps
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-3908
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bae-cation Palm Print Mini Dress
Look and feel like a total bae on vacay! This tropical mini dress is essential for exploring the island in style. It features a sleeveless, square neck, adjustable spaghetti straps, side ruched seams, and a brushed knit fabric offering a form-hugging fit and moderate stretch. Complete the look in espadrille wedges and earrings.
Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- Side ruched seams
- Form-hugging fit
- Mini-length hem
- Palm print, brushed knit-lined fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4557
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lush Paradise Lace-Up Mini Dress
Escape to a lush paradise in this tropical mini dress perf for your next island vacay! Featuring a sleeveless, square neck, spaghetti straps that lead to the open-back with a lace-up design, a bodycon silhouette, and palm print knit-lined fabric. Complete the look in sunglasses and heels.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Open-back, lace-up design
- Bodycon silhouette
- Mini-length hem
- Palm print, stretchy knit-lined fabric
- Fits true to size
Style Number/Barcode: 05102-4516
Category Name: Vacation Looks
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Palm Perfect Tropical Midi Dress
Look perfect in paradise wearing this palm print midi dress featuring a sleeveless, v-neck, spaghetti straps, a form-fitting silhouette, and a front slit accent on stretchy knit fabric. Complete your vacation look in wedges.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Form-fitting silhouette
- Front slit accent
- Midi-length hem
- Palm print, knit fabric with moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4542
Category Name: Vacation Looks
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale