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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Options Open O-Ring Midi Dress
Keep your options open and wear this dress for your weekend plans! It features a sleeveless, v-neck, spaghetti straps, an open-back with an o-ring insert, a bodycon silhouette, and a midi hem on stretchy rib-knit fabric. Complete the look with chic heels.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Open-back, o-ring insert
- Bodycon silhouette
- Midi hem
- Stretchy rib-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4659
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Bloom Floral Mesh Maxi Skirt
Serve a sultry vibe in this blooming floral printed mesh maxi skirt! Designed with ruched side seams to show off your curves, style with the matching tube top for a gorgeous look.
Shop Matching Top: Sultry Bloom Floral Mesh Tube Top
Fit & Features
- Sheer mesh fabric with full-length knit lining, high stretch
- Floral print
- High-rise waist
- Maxi-length hem, lettuce-edge trim
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06501-1142
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Flawless Halter Jumpsuit
You'll look and feel flawless in this vacay-worthy halter jumpsuit featuring a sleeveless, ruched bodice with keyhole cutouts, a tie-neck closure, a partial open-back, and a wide-leg silhouette. Complete the look in wedges for a sunset dinner.
Fit & Features
- Sleeveless, halter neck, tie closure
- Keyhole cutouts
- Ruched bodice
- Partial open-back design
- Wide-leg silhouette
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06502-1152
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Muse Chiffon Skater Dress
Showcase your effortless beauty in this airy chiffon skater dress. It features a sweetheart neckline with ruffled trim and a pleated bust, long bishop sleeves, a fitted high waistband, and a tiered skater skirt with a short hem and a fit and flare silhouette. Style this skater dress with your fave mules.
Fit & Features
- Sweetheart neckline, ruffled trim, pleated bust
- Long sheer bishop sleeves, cinched hems
- Smocked back design, fitted high waistband
- Fit and flare silhouette
- Tiered skater short-length skirt
- Chiffon fabric fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1650
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Sleeveless Faux Leather Corset
Step up your night out 'fit with this sleek sleeveless faux leather corset. It features a V-neckline, tank shoulder straps, a partially open back with lower hook and eye closures, a corset-designed front with an asymmetrical cropped hem, and a form-hugging fit. Style with a mini skirt and heels.
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Open back, lower hook and eye closures
- Corset-designed front, asymmetrical cropped hem
- Form-hugging fit
- Faux leather fabric
- Runs true to size
Style Number/Barcode: 06003-1957
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Fling Twist Front Crop Top
So much for a summer fling! With this crop top, you're sure to fall for it over and over again. It features a sleeveless, sweetheart neck, criss-cross back straps, and a twisted front on lined knit fabric. Complete your look with the matching bottoms.
Shop Matching Bottoms: Summer Fling Twist Slit Maxi Skirt
Fit & Features
- Sleeveless, sweetheart neck, spaghetti straps
- Criss-cross back straps
- Twisted front
- Cropped hem
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4374
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flutter And Fly Butterfly Earrings
Flutter and fly into these chic earrings featuring rhinestone butterfly charms along the dainty chain links and a post-back closure. Complete the look in a flirty skater dress.
Fit & Features
- Rhinestone butterfly charms
- Dainty chain links
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1343
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Fling Twist Slit Maxi Skirt
So much for a summer fling! With this maxi skirt, you're sure to fall for it over and over again. It features a high-rise waist with a twist accent, a front high-cut slit, and a form-fitting silhouette on lined knit fabric. Complete your look with the matching top.
Shop Matching Top: Summer Fling Twist Front Crop Top
Fit & Features
- High-rise waist with twist accent
- Front high-cut slit
- Form-fitting silhouette
- Maxi-length hem
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0673
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tequila And Friends Graphic Tee
Haven't you heard? You in this graphic tee plus friends equals one great night! It features short sleeves, a crew neck, a front script that reads, "Tequila And Friends Make A Great Blend", and a cropped hem. Complete the look in sleek skinny pants and heels.
Fit & Features
- Short sleeves
- Crew neck
- Front graphic with "Tequila And Friends Make A Great Blend"
- Cropped hem
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06002-1398
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Two Moods Sweater Knit Halter Top
Why blend in when you can stand out in this sweater halter top featuring a sleeveless, two-toned bodice, tie-back neck closure, a partial open-back, and a cropped hem on stretchy rib-knit fabric. Complete the look in boyfriend jeans.
Fit & Features
- Sleeveless, halter neck
- Tie-back neck closure
- Two-toned bodice
- Partial open-back
- Cropped hem
- Sweater rib-knit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1492
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Summertime Glam Slide-On Sandals
Bring that glam vibe you love to your casual summertime look! These slide-on sandals feature a round toe, a dual banded strap design with braided woven detailing in a trendy metallic hue, and a flat sole. Style with your fave summer dress and sleek hoops.
Fit & Features
- Slide-on fit
- Round toe
- Dual banded strap design, braided woven detailing, metallic hue
- Flat sole, faux leather material
- Runs true to size
Style Number/Barcode: 07404-1073
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Give A Twirl Linen Skater Dress
Have your twirl-worthy moment in this linen skater dress perfect for casual parties! It features three-quarter-length puff sleeves with ruffled hems, a square neckline, a babydoll-style seam, a flirty open-back with an elasticized lattice strap, and a short-length hem with a flared-out skater silhouette. Complete the look in this skater dress with strappy stiletto heels.
Fit & Features
- Three-quarter-length puff sleeves, ruffled elastic cinched hems
- Square neckline
- Babydoll style seam
- Open-back, elasticized lattice strap
- Short skater silhouette
- Plaid linen fabric, lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4717
Category Name: Vacation Looks
Price: $5.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On An Adventure Corduroy Utility Romper
This corduroy romper will inspire your next adventure! It features short sleeves, a collared neckline, front zipper closure and flap pockets, an adjustable belted waist with belt loop accents, back pockets, and a form-fitting silhouette. Complete the look in cool sunglasses and thigh-high boots.
Fit & Features
- Short sleeves
- Collared neckline
- Front zipper closure and flap pockets
- Adjustable belted waist, belt loop accents, back pockets
- Form-fitting silhouette
- Corduroy fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06303-0168
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Country Chic Faux Suede Romper
Look chic in the countryside in this faux suede romper showcasing a flirty silhouette with a front twist accent, sleeveless v-neckline, spaghetti straps, and flowy shorts. Complete the look with a straw hat for wine tasting.
Fit & Features
- Sleeveless, v-neckline
- Spaghetti straps
- Front twist accent
- Flowy shorts
- Faux suede fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06503-1004
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Finders Keepers Chiffon Romper
Lucky you to have found this chiffon romper for keeps! It features a sleeveless, square neck, spaghetti straps, an open tie-back design, high waist seam, and a ruffled overlay with shorts lining. Complete your trendy look in espadrille wedges.
Fit & Features
- Sleeveless, square neck
- Spaghetti straps
- Open tie-back design
- High waist seam
- Ruffled overlay, shorts lining
- Airy chiffon lined fabric, no stretch
- Fits true to size
Style Number/Barcode: 06403-0243
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bloom Baby Floral Halter Cutout Mini Dress
Soft, flirty, and ready for golden hour—this halter mini dress is a little bit sweet, a little bit daring. Flowy ruffles and a smocked waist keep the vibe effortlessly pretty for sunset dinners or dressy events!
Fit & Features
- Floral print, chiffon woven fabric, woven lining
- Sweetheart twist halter neckline, tie straps
- Cutout bust accent
- Stretchy, smocked, fitted bodice
- Drop waist seam
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000243
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Night Out Crepe Romper
Have a chic night out in this alluring crepe romper! It features a sleeveless square neckline, spaghetti straps, an open back with a tie-back design, a front waist cutout, and fitted shorts with an envelope skirt overlay. Style with strappy mules and a sleek clutch.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open-back, tie-back design
- Front waist cutout
- Fitted shorts, envelope skirt overlay
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1010
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Just A Slice Cutout Crop Top
You know you'd like to have a slice of this cami crop top! It features a sleeveless, v-neck, spaghetti straps, and cut-out accents along the front on brushed knit fabric with a moderate stretch. Perfect for layering under a sheer top for an eye-catching look.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Cut-out accents along the front
- Cropped hem
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06001-4360
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dress Code Mesh Marble Crop Top
The dress code this season calls for this mesh marble crop top paired with your fave bottoms! It features long sleeves, a square neck, and dual tie-front closures that add eye-catching detail. Complete the look in wide-leg pants and heels.
Fit & Features
- Long fitted sleeves
- Square neck
- Dual tie-front closures
- Cropped hem
- Marble print
- Sheer mesh fabric, front knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4348
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mary Tie-Waist Mini Skirt by Windsor Denim
Create adorable everyday looks with the Mary mini skirt by Windsor Denim! It features a high-rise waist, a trendy tie-front belt, a mini-length frayed hem, and a form-hugging fit. The denim fabric offers minimal stretch. Style with a fitted bodysuit and strappy mules.
Fit & Features
- High-rise waist
- Tie-front belt
- Mini-length frayed hem
- Form-hugging fit
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06601-0060
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Everyday Essential Racerback Tank Top
This soft brushed knit tank top is an everyday essential you can dress up or down! It features a sleeveless scoop neckline, tank shoulder straps with a racerback design, and a mid-length, form-hugging fit. Style with your fave pair of denim and slides for a cute and casual look.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps, racerback design
- Mid-length, form-hugging fit
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1184
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Leo Jersey Graphic Tee
Let this graphic tee do the talking! It features classic cap sleeves, a crew neck, a front script that reads, "Leo Give Me Space & Attention", and a cropped hem on smooth jersey knit fabric. Complete the look in a sleek mini skirt for a birthday celebration.
Fit & Features
- Cap sleeves
- Crew neck
- Front script reads, "Leo Give Me Space & Attention"
- Cropped hem
- Smooth jersey-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1404
Category Name: Vacation Looks
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rare Marble Pattern Midi Dress
Why blend in when you can stand out! Strut into the party in this marble midi dress featuring a trendy, sleeveless, square neck, bungee spaghetti straps, and a bodycon silhouette. Complete the look in doorknocker earrings.
Fit & Features
- Sleeveless, square neck
- Bungee spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Marble pattern
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4723
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Out Of Office Ruched Mini Dress
Log off and get ready for a relaxing getaway in this ruched knit mini dress. It features a sleeveless cowl neckline, spaghetti straps, ruching down one side leading to an adjustable drawstring, and a mini-length, asymmetrical hem. The smooth knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals and your favorite shades.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- High waist seam
- Ruching down one side seam, adjustable drawstring
- Short, curve-hugging, bodycon silhouette, asymmetrical hem
- Stretchy knit fabric, tropical palm leaf print
- Runs true to size
Style Number/Barcode: 05102-4691
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale