Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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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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Vacay Mode Tropical V-Neck Midi Dress
Enter vacay mode with the perfect tropical midi dress that'll have you looking fabulous! It features a sleeveless V-neckline, adjustable spaghetti straps, a form-hugging silhouette, and a sultry side slit cutout. Complete the look in chic mules for a dinner by the beach!
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Form-hugging silhouette
- Side slit cutout, slit
- Midi-length hem
- Tropical palm leaf print, stretchy knit fabric, bust lining
- Runs true to size
Style Number/Barcode: 05102-5056
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miami Mood Tropical Print Cutout Maxi Dress
This alluring tropical print maxi dress is an iconic pick for a summer vacay to Miami! It features a sleeveless halter neckline with cross-front straps, a sultry center bust cutout followed by a chic O-ring accent, dual waist cutouts on each side, a backless design with dual tie-back straps, a floor-length hem with dual thigh-high front slits, and a flowy A-line silhouette. The lightweight woven fabric showcases an all-over tropical palm leaf pattern. Style with hoop earrings and clear mules.
Fit & Features
- Sleeveless halter neckline, cross-front straps, tie-back design
- Center bust cutout, O-ring accent, dual waist cutouts
- Backless design, dual tie-back straps, elasticized back waistband
- Floor-length hem, dual high front slits, A-line silhouette
- Tropical palm leaf print
- Woven fabric, lined bust, no stretch
- Runs true to size
Style Number/Barcode: 05102-5087
Category Name: Vacation Looks
Price: $5.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tie The Knot Rhinestone Flat Sandals
Tie your outfit together by sliding into these statement-flat sandals! Featuring a round toe, a PVC clear strap with multiple rhinestone embellished straps that form a trendy knot design, and a faux leather footbed. Style with a chic ring set for added sparkle!
Fit & Features
- Round toe
- PVC clear strap
- Multiple rhinestone embellished straps, knot design
- Faux leather footbed
- Flat sole
- Runs a 1/2 size bigger
Style Number/Barcode: 07404-1127
Category Name: Vacation Looks
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual-Chic Style Muse High Slit Maxi Dress
Show off your elevated casual-chic style in this high slit maxi dress. Featuring a sleeveless crew neckline with tank shoulder straps, trendy side cutouts at the waist, a maxi-length hem, and a thigh-high side slit, this dress will get you major compliments. The ribbed knit fabric offers plenty of stretch. Complete the look with sleek hoops and strappy heels.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Dual side cutouts at the waist
- Maxi-length hem
- High side slit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4866
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feel The Breeze Palm Print Mesh Duster
Feel the island breeze everywhere you go in this palm print duster featuring long sleeves, an open front design, and a flowy silhouette on sheer mesh fabric. Layer over a basic bodysuit and denim shorts for a cute vacation look!
Fit & Features
- Long sleeves
- Open front design
- Flowy silhouette
- Duster length hem
- Palm print
- Sheer mesh fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06202-0405
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple And Sultry Cutout Midi Dress
Simple and sultry, this cutout midi dress will make a chic impression. It features a sleeveless V-neckline with ruching and a center O-ring accent, spaghetti straps, a front waist cutout, a midi-length hem with a thigh-high front slit, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with lace-up heels.
Fit & Features
- Sleeveless V-neckline, ruched, center metal O-ring accent
- Spaghetti straps
- Front waist cutout, high waist
- Midi-length hem, high front slit
- Curve-hugging fit
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-2298
Category Name: Vacation Looks
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feelin' Artsy Abstract Print Cutout Jumpsuit
You'll be feelin' artsy and chic in this alluring abstract print jumpsuit. It features a sleeveless plunging V-neckline with a padded bust, halter spaghetti straps with a tie-back design, and a small center cutout with a metal accent under the bust. The waist has dual cutouts on each side with chunky chain-link accents connected to straps for a bold vibe, an open back with dual tie-back straps, and a wide-leg silhouette with a relaxed fit. The woven fabric showcases an all-over multi-colored abstract print pattern that will catch everyone's eye. Style with espadrille sandals.
Fit & Features
- Sleeveless plunging V-neckline, padded bust
- Halter spaghetti straps, tie-back design
- Small center cutout under the bust, metal accent
- Dual waist cutouts, chain-link accents connected to straps
- Open back, dual tie-back straps, lower back zipper, hook and eye closure
- Wide-leg silhouette, relaxed fit
- Multi-colored abstract print, woven fabric, knit lining at the bust, minimal stretch
- Runs true to size
Style Number/Barcode: 06402-1326
Category Name: Vacation Looks
Price: $6.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Weekend Plans Wide-Leg Pants
These airy and chic wide-leg pants are perf for your casual weekend plans. They feature a high-rise elasticized waist, a faux front drawstring, dual front pockets, and a relaxed fit with a wide-leg silhouette. The lightweight gauze fabric has no stretch. Style with a crop top and sandals for a breakfast date.
Fit & Features
- High-rise elasticized waist
- Faux front drawstring
- Dual front pockets
- Relaxed fit, wide-leg silhouette
- Gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0778
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Passport To Paradise Tropical Print Ruched Midi Dress
Whether you're headed on a weekend getaway or a plane ride to paradise, pack this tropical print midi dress for a gorgeous glow! It features a sleeveless cowl neckline, spaghetti straps, ruching down one side seam, an asymmetric midi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The smooth and stretchy knit fabric features an all-over tropical palm leaf print. Style with espadrille sandals.
Fit & Features
- Sleeveless cowl neckline, spaghetti straps
- Ruched side seam
- Asymmetric midi-length hem, high side slit
- Bodycon fit
- Tropical palm leaf print
- Knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5136
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirtatious Charm Cutout Midi Dress
Say hello to this adorable cutout midi dress that will bring those cute and fun vibes! This midi dress features an off-the-shoulder sweetheart neckline and short fitted sleeves. The center knot detail at the bust with a tie-front adds a charming touch, while the dual waist cutouts add a hint of playfulness. The midi-length hem with a high side slit showcases your legs for a sassy look. With its form-hugging silhouette and ribbed knit fabric offering plenty of stretch, this dress ensures both comfort and style. Complete your outfit with a pair of sandals to bring that flirtatious charm!
Fit & Features
- Off-the-shoulder sweetheart neckline
- Center knot detail at the bust, tie-front design
- Dual waist cutouts
- Midi-length hem, high side slit
- Form-hugging fit
- Ribbed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4992
Category Name: Vacation Looks
Price: $6.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bohemian Girl High Rise Flare Pants
Unleash your inner bohemian girl in these flare pants at festivals and concerts this season! Featuring a flattering high-rise waist, hip-hugging fit, and a flared hem. The pants are designed with a boho-inspired print on brushed stretchy knit fabric. Complete the look with the matching top.
Shop Matching Top: Bohemian Girl Halter Tie Crop Top
Fit & Features
- High-rise waist
- Hip-hugging fit
- Flared hem
- Boho print
- Brushed stretchy knit fabric
- Runs true to size
Style Number/Barcode: 06502-2338
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bohemian Girl Halter Tie Crop Top
Unleash your inner bohemian girl in this halter crop top at festivals and concerts this season! Featuring a sleeveless plunge halter V-neckline, dual front ties with a cutout accent, an open back, and a fitted crop hem. The top is designed with a boho-inspired multi-print on brushed stretchy knit fabric. Complete the look with the matching bottoms.
Shop Matching Bottoms: Bohemian Girl High Rise Flare Pants
Fit & Features
- Sleeveless plunge halter V-neckline
- Dual front ties, cutout accent
- Open back
- Fitted crop hem
- Boho multi-print
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 06001-4874
Category Name: Vacation Looks
Price: $4.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Breezy Paisley Tie-Front Top
Effortlessly breezy with bohemian charm! Style this paisley tie-front crop top with long bell sleeves with your favorite pair of denim bottoms and heels for a concert in the city or for drinks at a rooftop bar.
Fit & Features
- Long bell sleeves
- Plunge v-neckline
- Tie-front closure
- Cropped hem
- Paisley pattern
- Woven gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1389
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Fab Rhinestone Rectangular Frame Sunglasses
Create an iconic forever fab look with these sleek sparkly shades! The sunglasses feature a geometric rectangular-shaped design with a plastic frame, wide arms with mini rhinestone embellishments, and tinted lenses. Style with hoop earrings.
Fit & Features
- Geometric rectangular-shaped design
- Plastic frame
- Wide arms, mini rhinestones
- Tinted lenses
Style Number/Barcode: 07008-1019
Category Name: Vacation Looks
Price: $2.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Babe Town Floral Tie Front Top
Look like the babe of the town in this ditsy floral top featuring long bell sleeves, a tie-front closure, and a cropped hem on woven fabric. Complete the look in denim shorts for a coffee run.
Fit & Features
- Long bell sleeves
- Tie-front closure
- Cropped hem
- Ditsy floral print
- Woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1403
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pick Me Floral Lace-Up Maxi Dress
This floral maxi dress will be the first pick in your closet! It features a sleeveless V-neckline with a knotted bust, spaghetti straps that creates the open lace-up back design, and a flowy slim silhouette. Complete the look in cute new sandals for a baby shower or casual lunch out!
Fit & Features
- Sleeveless V-neckline, knotted bust
- Spaghetti straps
- Lace-up open back
- Flowy slim silhouette
- Maxi-length hem
- Floral print, breezy woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4947
Category Name: Vacation Looks
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh In Paisley Floral A-Line Dress
Serve your closet a fresh style by adding this paisley floral short dress to it! Featuring a sleeveless V-neckline, sleek bungee spaghetti straps, a flattering A-line silhouette, and a flirty slit hem. Complete the look in trendy sandals for an afternoon in the city!
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- A-line silhouette
- Short-length hem, slit accent
- Paisley floral print
- Smooth stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4943
Category Name: Vacation Looks
Price: $5.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Beach Boardwalk Stroll Cutout Denim Romper
This adorable cutout denim romper is perfect for a stroll along a beach boardwalk this summer! It features a sleeveless plunging neckline with ruching, cross-front halter spaghetti straps with a tie-back design, a bold front waist cutout, a high-rise waist, and fitted shorts. The cotton-blend denim fabric offers a moderate stretch. Style with slip-on sandals and trendy shades.
Fit & Features
- Sleeveless plunging neckline, ruching
- Cross-front halter spaghetti straps, tie-back design
- Front waist cutout, high-rise waist
- Fitted shorts
- Back zipper, hook and eye closure
- Cotton-blend denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0343
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Cruise Tropical Print Strapless Jumpsuit
Create a picture-perfect 'fit for a sunset cruise with this tropical-printed jumpsuit! Featuring a strapless straight-across neckline, a ruched high waist, a flattering wide-leg silhouette, and an all-over palm leaf print, this jumpsuit will capture those summer vibes. Style with espadrille sandals.
Fit & Features
- Strapless straight-across neckline
- Ruched high waist
- Wide-leg silhouette
- Tropical palm leaf print
- Stretchy knit fabric, bust lining
- Runs true to size
Style Number/Barcode: 06502-2350
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Summer Style Ditsy Floral Bustier Top
Step out this summer in flirty casual 'fits with this ditsy floral bustier top. It features a sleeveless square neckline, tie-shoulder spaghetti straps, structured underwire, front hook and eye closures, and a cropped, ruffled hem. The ditsy floral printed knit fabric offers a moderate stretch. Style with light-wash denim and slide-on sandals.
Fit & Features
- Sleeveless square neckline
- Tie-shoulder spaghetti straps
- Structured underwire, front hook and eye closures
- Cropped ruffled hem, fitted silhouette
- Ditsy floral print
- Ribbed knit fabric, front lining, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4657
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Stylish Ribbed Knit Midi Dress
This simple yet chic ribbed knit midi dress is the casually stylish staple you need. It features a sleeveless scoop neckline, thin tank shoulder straps, a midi-length hem, and a curve-hugging silhouette. The lined knit fabric offers plenty of stretch. Complete the look with a denim jacket and clear mules.
Fit & Features
- Sleeveless scoop neckline
- Thin tank shoulder straps
- Midi-length hem
- Form-hugging fit
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5077
Category Name: Vacation Looks
Price: $5.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect And Posh Pearl Choker Necklace
Perfect and posh will be your vibe with this pretty pearl choker necklace! It features a thin metal zig-zag design with round faux pearl embellishments and small metal bead accents. Style with duster earrings for a complete glam look.
Fit & Features
- Thin metal zig-zag design
- Round faux pearls
- Small metal bead accents
- Adjustable chain, lobster clasp closure
Style Number/Barcode: 07002-1490
Category Name: Vacation Looks
Price: $2.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Marvelous Style Marble Print Maxi Dress
Showcase a marvelous style in this trendy marble print maxi dress! It features a sleeveless square neckline, spaghetti straps, an asymmetric side cutout at the waist to add a sultry vibe, ruching down one side seam with an adjustable drawstring, an asymmetric maxi-length hem creating a thigh-high side slit, and a curve-hugging silhouette. The all-over eye-catching marble print pattern on the smooth and stretchy knit fabric will draw all the attention to you! Complete your summer party look with clear heels.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Asymmetric side cutout at the waist
- Ruching down one side seam, adjustable drawstring
- Asymmetric maxi-length hem, high side slit, curve-hugging fit
- Marble print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5119
Category Name: Vacation Looks
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Boho Dream Cropped Tie-Front Top
Create a dreamy boho-chic look with this cropped tie-front top! It features short sleeves, a V-neckline with a tie-front design, and a fitted cropped hem. The airy gauze fabric has no stretch. Style with a trendy bralette and high-rise denim shorts for casual weekend plans.
Fit & Features
- Short sleeves
- V-neckline
- Tie-front design
- Fitted cropped hem
- Lightweight gauze fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1180
Category Name: Vacation Looks
Price: $11.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free