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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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
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Pretty Glam Rhinestone Pearl Buckle Slide Sandals
Adorn your feet in these glam rhinestone faux pearl slide sandals with dual buckle straps and a comfortable footbed. Pair with a tote bag for a beach day.
Fit & Features
- Round toe
- Dual buckle straps with rhinestone, faux pearl trim
- Comfortable footbed
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1284
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Remy High Rise Cut Off Shorts By Windsor Denim
Showcase your cute curves in the Remy jean shorts by Windsor Denim! They feature a flattering high-rise waist, cut-off style hem, and a vintage-inspired color fade effect on premium denim fabric. Complete the look in a flirty crop top for a beach day.
Fit & Features
- High-rise waist
- Cut-off style hem
- Color fade effect
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Form-hugging, denim fabric
- Fits true to size
Style Number/Barcode: 06603-0278
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cancun Vacay Tropical Slit Maxi Skirt
Cancun isn't ready for this one! Jet set on vacay in this tropical maxi skirt featuring a high-rise elasticized waistband, a front high slit, floral and leaf pattern, and a maxi-length hem on gauze woven fabric. Style with the matching tropical top.
Shop Matching Top: Cancun Vacay Tropical Multi-Wear Top
Fit & Features
- High-rise elasticized waistband
- Front high slit
- Floral and leaf pattern
- Maxi-length hem
- Relaxed silhouette
- Gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06301-0078
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cancun Vacay Tropical Multi-Wear Top
Cancun isn't ready for this one! Jet set on vacay in this tropical halter top featuring multi-wear straps so you can style it as a halter or tube top, floral and leaf pattern, and a cropped hem. Style with the matching tropical maxi skirt.
Shop Matching Skirt: Cancun Vacay Tropical Slit Maxi Skirt
Fit & Features
- Multi-wear straps
- Cropped hem
- Back smocked panel
- Floral and leaf pattern
- Gauze woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1297
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chill Factor Paisley Boho Pants
Easy, breezy, and so chill in these paisley boho pants featuring a high rise waist, form-fitting silhouette, and a flared hem. Complete the look in a cute crop top for spring festivals.
Fit & Features
- High rise waist
- Form-fitting silhouette
- Flared hem
- Paisley boho-inspired print
- Fits true to size
Style Number/Barcode: 06502-0869
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Natural Beauty Tropical Maxi Dress
Explore a tropical island looking naturally beautiful in this palm print maxi dress featuring a sleeveless, square neck, halter straps, an open back with tie, bodycon silhouette, and a front twist accent atop a sultry slit. Complete the look in a straw floppy hat.
Fit & Features
- Sleeveless, square neck, halter straps
- Open-back with tie
- Bodycon silhouette
- Front twist accent and slit
- Maxi-length hem
- Tropical palm print, knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4720
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale