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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Spine Chilling Eyelash Knit Sweater
This eyelash knit sweater may give you chills at how cute it is! The sweater features long sleeves with cuffs, a mock neckline, cropped hem, and a partial open-back design with tie closure. Complete the look in a mini skirt and boots.
Fit & Features
- Long sleeves with cuffs
- Mock neckline
- Cropped hem
- Partial open-back design tie closure
- Fuzzy eyelash knit
- Fits true to size
Style Number/Barcode: 06005-1480
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweeten Up Strappy Back Floral Chiffon Skater Dress
Sweeten up any moment in this floral chiffon skater dress perfect for celebrations and showers! With a square neckline, spaghetti straps, and a playful strappy back design, this dress is perfect for any occasion. The skater silhouette and ruffled short-length hem add a flirty touch, while the ditsy floral print and chiffon fabric keep it light and whimsical. Complete the look in wedges.
Fit & Features
- Ditsy floral print, chiffon fabric lined with stretchy knit
- Spagehtti straps, square neckline
- Strappy back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5450
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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There She Goes High-Rise Slit Boyfriend Jeans
These denim boyfriend jeans were made to be seen on you! They feature a flattering high-rise waist, trendy relaxed boyfriend style leg with knee slit accents on premium denim fabric. Style with a chic corset top for dinner and drinks with your honey!
Fit & Features
- High-rise waist
- Relaxed boyfriend-style leg
- Knee slit accents
- Front five-button closure
- Five-pocket styling, belt loop accents
- Premium denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06602-0428
Category Name: Vacation Looks
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simple Glam Moment Bodysuit
Showcase simple glam vibes in this glitter knit bodysuit that was made for a night out. It features a wrap-front design with a V-neckline, long fitted sleeves, a high waist seam, and a knit bottom. Style this shimmery bodysuit with faux leather pants and strappy heels.
Fit & Features
- Wrap-front design, V-neckline
- Long fitted sleeves
- High waist seam
- Knit bottom
- Glitter knit fabric
- Runs true to size
Style Number/Barcode: 06001-4482
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Sleek Faux Leather Blazer
Layer on this elevated sleek faux leather blazer for a city-chic vibe. It features a lapel collar, long cuffed sleeves, front pockets, and a relaxed silhouette. The patent faux leather fabric offers a moderate stretch. Style with hoop earrings and a chain necklace.
Fit & Features
- Lapel collar
- Long sleeves, cuffed hems
- Front pockets
- Long-length hem
- Relaxed fit
- Patent faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06204-1485
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Adventures Halter Tie Front Crop Top
A halter crop top for all of your cute adventures this season! This top is designed with a flirty dual tie-front design and a bold center split and delicate sheer crop hem create the perfect balance of daring and feminine charm.
Fit & Features
- Crinkle texture sheer woven fabric, bust lining
- Plunge halter neckline with tie closure
- Dual tie front
- Center split, sheer crop hem
- Runs true to size
Style Number/Barcode: 06003-000039
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Cute To Catch Belted Ruffle Skort
Catch her if you can—she’s booked, busy, and best dressed. This ruffled mini skort brings all the bounce for brunch, day parties, and spontaneous Insta moments.
Fit & Features
- Woven fabric
- High-rise belted waist, belt loop accents
- Hidden side zipper and hook-eye closure
- Ruffled skirt overlay, shorts lining
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06403-000025
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Country Vibes Cowboy Boot Bag
Show off those trendy country vibes with this adorable cowboy boot bag! Featuring a cowboy boot shape with a center star accent, a cow print pattern, and an included chain-link shoulder strap, this bag is perfect for music festivals to keep all of your essentials on hand. Style with a rhinestone fringe denim jacket and boots!
Fit & Features
- Cowboy boot shape
- Center star accent
- Cow print pattern
- Top zipper closure
- Included chain-link shoulder strap
- Faux leather material, woven interior
Style Number/Barcode: 07203-1151
Category Name: Vacation Looks
Price: $19.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Thing High Rise Zebra Print Skort
Get wild for this zebra print skort and flaunt your fierceness! Featuring a high-rise waist and form-hugging fit, a front skirt overlay adds a touch of flirty fun, while the short lining offers comfort and coverage. Complete the look with the matching top.
Shop Matching Top: Wild Thing Corset Zebra Print Top
Fit & Features
- Zebra print, woven fabric, no stretch
- High rise waist
- Back zipper and hook-eye closure
- Form-hugging fit
- Skirt overlay, shorts lining
- Runs true to size
Style Number/Barcode: 06303-0252
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Ditsy Floral Eyelet Strapless Mini Dress
Keep your summer date 'fits flirty and stylish with this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a sweet ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with platform sandals and hoop earrings.
Fit & Features
- Ditsy floral print
- Stretchy eyelet knit fabric with knit lining
- Strapless straight neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5799
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Classic Plunge V-Neck Top
Ultra flattering and essential, this plunge v-neck top features long bishop sleeves and a ruched bodice for a figure-hugging fit. Complete the look in high-rise jeans for a dinner party.
Fit & Features
- Long bishop sleeves
- Plunge v-neck
- Ruched bodice
- Figure-hugging fit
- Sleek knit fabric
- Fits true to size
Style Number/Barcode: 06001-4393
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendsetting Vibes Faux Leather Shacket
Showcase chic trendsetting vibes when you layer on this sleek faux leather shacket. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, and a relaxed fit. The smooth faux leather fabric offers a moderate stretch. Style over a basic bodysuit with your fave pair of denim.
Fit & Features
- Collared neckline
- Long sleeves, single button detail
- Button-down front
- Buttoned chest pockets, dual lined side pockets
- Relaxed fit
- Faux leather fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06204-1369
Category Name: Vacation Looks
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pop Star Rhinestone High-Rise Denim Shorts
Put on a show arriving in these rhinestone denim shorts! They feature a flattering high-rise waist, and stunning rhinestone swag chains across the front for a touch of glamour. The distressed accents add a trendy edge, while the fitted hem ensures a perfect fit. Complete the look in a bodysuit and boots for a concert or music festival!
Fit & Features
- High-rise waist
- Rhinestone swag chains across the front
- Distressed accents, fitted hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06603-0364
Category Name: Vacation Looks
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Main Style Ribbed Knit Tank Mini Dress
This adorable tank mini dress will be your new main style to create the cutest everyday looks! Designed with a stretchy ribbed knit fabric for comfortable wear, it features a sleeveless scoop neck and back, thin tank shoulder straps, and a bodycon silhouette to flaunt your figure. Pair this short dress with a denim jacket and sneakers for a coffee date with friends.
Fit & Features
- Stretchy ribbed knit fabric
- Scoop neck and back
- Thin tank straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1975
Category Name: Vacation Looks
Price: $8.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off Duty Babe Luxe Zip-Up Crop Hoodie
Elevate your off-duty look babe in this luxe crop hoodie perfect for running errands or coffee runs! It features relaxed long sleeves with elasticized cuffs, a hooded neckline, front zipper closure, functional pockets, and a cropped elasticized hem on stretchy scuba knit fabric. Layer over a basic top and pants.
Fit & Features
- Relaxed long sleeves, elasticized cuffs
- Hooded neckline
- Front zipper closure
- Functional pockets
- Cropped elasticized hem
- Stretchy and luxe scuba knit fabric
- Runs true to size
Style Number/Barcode: 06202-0379
Category Name: Vacation Looks
Price: $16.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Cute Striped Oversized Sweater
Layer on this casual cute striped oversized sweater for an adorable everyday 'fit! It features a high crew neckline, long dolman sleeves with tapered cuffs, and a mid-length hem with a relaxed fit. The knit fabric features an all-over striped pattern with thick and thin stripes. Pair with your favorite go-to jeans and ankle booties.
Fit & Features
- High crew neckline
- Long dolman sleeves, tapered cuffs
- Mid-length hem
- Oversized relaxed fit
- Striped pattern, thick and thin stripes
- Ribbed knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1436
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mermaid Mood Starfish and Seashell Earrings
Giving vacation vibes, even if you’re just at brunch. These earrings mix starfish, seashells, and faux pearls for a playful, ocean-inspired finish.
Fit & Features
- Starfish and seashell designs
- Faux pearl embellishments
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-000125
Category Name: Vacation Looks
Price: $3.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pearl-Fect Pick Sweater Maxi Dress
Forever a perfect pick for your next chic soiree! This sweater maxi dress features long fitted sleeves, a plunge V-neckline, a center front faux pearl button-down along the bodycon silhouette, and a slit accent. The ribbed knit fabric offers a moderate stretch. Complete the look with pointed-toe booties.
Fit & Features
- Sweater ribbed knit fabric, moderate stretch
- Long fitted sleeves
- Plunge V-neckline
- Center front faux pearl button-down
- Bodycon fit
- Front slit
- Runs true to size
Style Number/Barcode: 06005-1525
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Trendsetter Rhinestone Lace-up Skinny Jeans
You'll be a trendsetting muse in these glam rhinestone-accented skinny jeans! They feature a high-rise waist, a rhinestone embellished lace-up front, a skinny-leg silhouette, and a form-hugging fit. The denim fabric offers a moderate stretch. Complete the look with sparkly mules.
Fit & Features
- High-rise waist
- Rhinestone embellished lace-up front design
- Skinny-leg silhouette
- Five-pocket design, three belt loops
- Front button, hidden zipper closure
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06602-0389
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Style Warm Up Sweater Knit Dress
Cozy up this season in style! This sweater mini dress is the best of both worlds featuring cozy dolman sleeves, a surplice v-neckline, belted tie-front waist, and a bodycon silhouette. The dress is composed of soft cable and rib-knit fabric that offers plenty of stretch. Style with knee-high boots to complete the look!
Fit & Features
- Dolman sleeves
- Surplice v-neckline
- Belted tie-front waist, belt loop accents
- Bodycon silhouette, mini-length
- Cable and rib-knit sweater fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1572
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Don't Tempt Me Textured Slit Crop Top
Don't let your girls tempt you from taking this sultry crop top out for a good time! It features fitted long sleeves, an open V-neckline, a center front slit accent, and is composed of a textured sheer knit fabric. Complete the look in distressed denim jeans.
Fit & Fetaures
- Fitted long sleeves
- Open V-neckline
- Center front slit accent
- Cropped hem
- Textured sheer knit fabric
- Runs true to size
Style Number/Barcode: 06001-5267
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Allure One-Shoulder Cutout Waist Knit Midi Dress
Bring the bold allure to your summer 'fits with this sultry cutout waist midi dress! Made with a lined stretchy ribbed knit fabric, the mid-length dress features a sleeveless one-shoulder neckline and a tank strap with a trendy twisted-back design. The asymmetric goes around the waist, accented with a chic O-ring cutout at the front. The midi-length hem is detailed with a high-cut side slit along the figure-flaunting bodycon silhouette. Style with lace-up sandals for a weekend getaway!
Fit & Features
- Stretchy ribbed knit fabric, knit lining
- One-shoulder neckline, tank strap with twisted-back design
- Asymmetric waist cutout
- Front O-ring cutout
- High side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5697
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise Bound Tropical Floral Satin Midi Dress
You'll be ready to jet set off to paradise in this gorgeous tropical floral satin midi dress! The silky sleek satin woven fabric is accented with a blooming tropical floral print, an iconic look for your vacay getaway. The mid-length dress features a sleeveless V-neckline, adjustable spaghetti straps with a racer-back design, a flattering tie-back detail, and an asymmetric hanky hem with a flowy A-line silhouette for that effortless vibe. Style with hoop earrings and a layered necklace.
Fit & Features
- Tropical floral print
- Non-stretch satin woven fabric with top knit lining
- V-neckline
- Adjustable spaghetti straps, racer-back design
- Tie-back design
- Asymmetric hanky hem, A-line fit
- Runs true to size
Style Number/Barcode: 05101-3468
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Chic Side Slit Skort
Create a simply chic everyday outfit with this classic crepe skort. It features a high-rise waist, a back zipper closure, a mini-length overlay with a side slit, and fitted shorts. The crepe fabric offers a moderate stretch. Complete the look with a bodysuit and mules.
Fit & Features
- High-rise waist
- Back zipper closure
- Mini-length overlay, side slit
- Fitted shorts
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06503-1038
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale