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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Get The Look Crochet Halter Crop Top
Curate effortless vibes in this crochet halter crop top, perfect for pairing with the matching pants for a cute look!
Fit & Features
- Embroidered crochet fabric
- Halter plunge V-neck
- Crop hem
- Runs true to size
Shop The Matching Pants: Get The Look Crochet High-Rise Pants
Style Number/Barcode: 06003-000036
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Whirlwind Romance Floral Abstract Maxi Dress
This maxi dress is giving goddess in the wild. The sheer mesh and abstract floral print bring soft drama to any scene, whether it's brunch or rooftop party soirees!
Fit & Features
- Abstract floral print, mesh lined fabric
- Sweetheart neckline, padded bra cups, ruched bust seam
- Spaghetti straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-000242
Category Name: Vacation Looks
Price: $19.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: MAUVE
Available Size: XS, S, M
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
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Casual Staple Mock Neck Tank Top
This basic ribbed knit tank top is a casual staple to create the cutest looks! It features a sleeveless mock neckline, tank shoulder straps, and a fitted cropped hem. The lightweight ribbed knit fabric offers plenty of stretch. Style with your favorite pair of denim and hoop earrings.
Fit & Features
- Sleeveless mock neckline
- Tank shoulder straps
- Fitted cropped hem
- Ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1587
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend By The Bay Cotton Wide-Leg Pants
Create a chic relaxed look for a weekend by the bay in these lightweight cotton wide-leg pants. They feature an elasticized high-rise waist with an adjustable front drawstring, dual front pockets, and a casual wide-leg silhouette. The cotton fabric has no stretch. Pair with a crop top and sandals.
Fit & Features
- Elasticized high-rise waist
- Adjustable front drawstring
- Dual front pockets
- Wide-leg silhouette
- Cotton fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0773
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Sultry Vibes Cutout Maxi Dress
Bring the casual sultry vibes to your weekend plans with this curve-hugging maxi dress. It features a sleeveless sweetheart neckline with a twist-front design, spaghetti straps, a bold waist cutout at the front, a maxi-length hem with a chic back slit accent, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules for drinks with the girls.
Fit & Features
- Sleeveless sweetheart neckline, twist-front design
- Spaghetti straps
- Waist cutout
- Maxi-length hem, back slit
- Bodycon fit
- Ribbed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5186
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Chic Cutout Midi Sweater Dress
Create the perfect casual chic look with this of-the-moment sweater dress. It features a sleeveless scoop neckline with contrast piping, thin tank shoulder straps, a front waist cutout with matching contrast piping, a midi-length hem with a front slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Style with clear mules.
Fit & Features
- Sleeveless scoop neckline, contrast piping
- Thin tank shoulder straps
- Front waist cutout, contrast piping
- Midi-length hem, front slit
- Curve-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1700
Category Name: Vacation Looks
Price: $44.90
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Happy Face Statement Sunglasses
Complete your fab summer festival 'fits with these trendy statement sunnies! The sunglasses feature round-tinted lenses with a heart-eyed happy face cutout design, sleek metal arms, and rubber nose pads for support. Style with a rhinestone choker necklace.
Fit & Features
- Round-tinted lenses
- Heart-eyed happy face cutout design
- Thin metal arms
- Rubber nose pads
- Polycarbonate, blocks 100% UV
Style Number/Barcode: 07008-1032
Category Name: Vacation Looks
Price: $2.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Total Heartbreaker Statement Sunglasses
You'll be a total heartbreaker this season in these fabulous statement sunglasses. They feature heart-shaped black-tinted lenses with a dripping design, sleek metal arms, and rubber nose pads for support. Style with a layered choker necklace and hoop earrings for a summer concert.
Fit & Features
- Heart-shaped black-tinted lenses
- Dripping design
- Thin metal arms
- Rubber nose pads
- 100% UV protection
Style Number/Barcode: 07008-1034
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free