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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Eye-Catching Allure Printed Flare Pants
Give off an eye-catching allure in these artsy and bold printed flare pants. They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, a flared hem, and a trendy brush stroke print design. Style with a crop top and sandals.
Fit & Features
- High-rise waist
- Hip-hugging fit
- Form-hugging fit throughout the legs
- Flared hem
- Brush stroke print
- Stretchy brushed knit fabric
- Runs true to size
Style Number/Barcode: 06502-2263
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cali High-Rise Cross Waist Shorts By Windsor Denim
Create the illusion of a sleek and chic hourglass figure in the Cali shorts by Windsor denim! They feature a flattering high-rise asymmetrical cross waist and an on-trend raw cut-off hem on premium medium-wash denim with color fading. Complete the look in a breezy crop blouse for a beach date!
Fit & Features
- High-rise asymmetrical cross waist
- Raw cut-off hem
- Front five button-fly closures
- Five-pocket styling, belt loop accents
- Premium medium wash denim, color fading
- Minimal stretch
- Runs true to size
Style Number/Barcode: 06603-0310
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Daytime Chic Floral Ruffled Romper
Create a daytime chic look for weekend brunch or a garden party with this adorable romper! It features a sleeveless sweetheart neckline with a ruched and padded bust and a tie-front accent, adjustable spaghetti straps, a high waist seam, fitted shorts with a cute ruffled hem, and a dainty garden floral print pattern on the lightweight woven fabric. Style with strappy mules.
Fit & Features
- Sleeveless sweetheart neckline
- Ruched and padded bust, tie-front detail
- Adjustable spaghetti straps, back zipper and hook-eye closure
- High waist seam, fitted shorts, ruffled hem
- Garden floral print
- Lined smooth woven fabric
- Runs true to size
Style Number/Barcode: 06403-0301
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Paisley Passion Side Cutout Romper
Have a passion for paisley? Travel to your next destination in this boho sleeveless romper featuring a V-neck, wide shoulder straps, dual elasticized lattice cutouts on the side, a partial open-back, and a form-fitting silhouette. Complete the look in lace-up heels.
Fit & Features
- Sleeveless, V-neck, wide shoulder straps
- Dual elasticized lattice cutouts on the side
- Partial open-back
- Form-fitting silhouette
- Short-length hem
- Paisley print, woven fabric
- Runs true to size
Style Number/Barcode: 06303-0216
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Desert Heat Crochet Striped Crop Top
Everyone will feel the heat of your style in this crochet striped crop top perfect for those desert festivals and pool parties! It features a sleeveless halter V-neckline, dual tie-back straps, an open back, and an ultra-cropped hem. Complete the look in trendy bottoms.
Fit & Features
- Sleeveless halter V-neckline
- Dual tie-back strap closures
- Open back
- Ultra cropped hem
- Striped crochet design
- Runs true to size
Style Number/Barcode: 06005-1635
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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No Paparazzi Please Rectangle Sunglasses
Serving celeb-off-duty realness, no autographs today babe. These chunky rectangle sunglasses are the perfect finishing touch for brunch ‘fits, airport looks, or your iced-latte errand run.
Fit & Features
- Thick acetate-style frames with a glossy finish
- Edgy rectangle silhouette
- Dark-tinted lenses
Style Number/Barcode: 07008-000081
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Show Up In Style Linen Wide Leg Trouser Pants
Show up in these stylish linen trouser pants to create an effortlessly chic look! They feature a high-rise belted waist, belt loop accents, hidden side pockets, and front pleating going down the wide-leg silhouette. The lightweight linen fabric includes a woven lining. Complete the outfit in strappy-heeled sandals for a daytime casual soiree or a lunch date!
Fit & Features
- High-rise belted waist, metal buckle, belt loop accents
- Hidden front zipper, hook and bar closure
- Hidden side pockets
- Front pleating
- Wide-leg silhouette
- Linen fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06302-0748
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dreamy Summer Vibes Mesh Tie-Front Top
Show off those dreamy summer vibes in this sheer mesh multi-colored top! Featuring long fitted sleeves, a tie-front design creating a V-neckline, a fitted, cropped hem, and a bold multi-color printed design, this top is the perfect lightweight layer for the season. Style over a basic bodysuit with denim shorts.
Fit & Features
- Long fitted sleeves
- Tie-front design, V-neckline
- Fitted, cropped hem
- Multi-color printed design
- Sheer mesh fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06202-0376
Category Name: Vacation Looks
Price: $4.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Sensation Floral Chiffon Lace Romper
You'll be a trendy sensation in this floral chiffon romper to create a breezy and cute look for family parties or celebrations! Featuring a sleeveless V-neck with button front accents, adjustable spaghetti straps, an eye-catching lace back design, and a flowy short hem. Complete the look in a chic layered necklace.
Fit & Features
- Sleeveless V-neck, button front accents
- Lace-back design, zipper and hook-eye closure
- Adjustable spaghetti straps
- Flowy short hem
- Watercolor floral print
- Chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 06403-0249
Category Name: Vacation Looks
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Oh My Darling Floral Halter Mini Dress
Let your crush know you've entered the room in this retro-cute mini dress perfect for getting their attention at parties! It features a sleeveless sweetheart neckline with a flirty ruffle trim, halter straps with tie-back closure, an underwire bust, a bodycon silhouette, and a curved ruffle trim hem. The dress is designed with an adorable ditsy floral print on mesh-lined fabric. Complete the look in strappy mules.
Fit & Features
- Sleeveless sweetheart neckline, ruffle trim
- Halter straps, tie-back closure
- Underwire bust
- Bodycon silhouette
- Ruffle trim, curved mini-length hem
- Ditsy floral print, mesh-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4892
Category Name: Vacation Looks
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In The Sun Strappy Platform Wedges
Your feet deserve a sweet treat in these faux leather wedges perfect for your next day in the sun! They feature an almond toe, platform sole, a thin strappy design, wrap-around ankle strap with buckle closure. Style with a flirty sundress for a picnic date!
Fit & Features
- Almond toe
- Thing strappy design
- Wrap-around ankle strap, buckle closure
- Platform sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07406-0321
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Free Spirit Turquoise Choker Necklace
Channel that free spirit energy with this boho-chic choker necklace! It features a chain-link row with hanging teardrop-shaped accents with turquoise embellishments and a dainty draped chain design. Style with fringe earrings.
Fit & Features
- Chain-link row
- Hanging teardrop-shaped accents, turquoise embellishments
- Dainty draped chains
- Back adjustable chain, lobster clasp closure
Style Number/Barcode: 07002-1473
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strut Your Glam Rhinestone Flat Sandals
Look glam when the heels come off in these faux leather flat sandals! They feature an on-trend square toe, a wide strap, and a gorgeous oval rhinestone centerpiece. Style with a clutch purse to complete the look!
Fit & Features
- Square toe
- Wide strap
- Rhinestone oval centerpiece
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1125
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spread The Fun Butterfly Thong Sandals
Spread your wings and have fun with your fashion in these flat sandals featuring a jeweled butterfly charm, round toe with a thong-style strap, and dual foot straps on faux leather material. Complete the look with a ring set.
Fit & Features
- Round toe
- Jeweled butterfly charm
- Thong-style toe strap
- Dual foot straps
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1134
Category Name: Vacation Looks
Price: $6.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spring Into Style Espadrille Platform Heels
Spring into these stylish espadrille heels for the warmer season ahead! They feature an almond toe, wide toe strap, chunky platform sole, a block heel, and an ankle strap with buckle closure. Complete the look with a trendy handbag.
Fit & Features
- Almond toe
- Wide toe strap
- Chunky platform sole
- Block heel
- Ankle strap with buckle closure
- Espadrille material
- Runs true to size
Style Number/Barcode: 07401-4206
Category Name: Vacation Looks
Price: $9.97 $43.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Happily In Love Scoop Neck Mini Dress
You'll be happily in love with how stunning you look in this sleeveless mini dress for a graduation or birthday brunch! It features a scoop neck with a flirty bust tie, spaghetti straps, and a bodycon silhouette on rib knit fabric with a stretchy knit lining. Complete the look in trendy wedges.
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Bust tie
- Bodycon silhouette
- Mini-length hem
- Rib knit, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4754
Category Name: Vacation Looks
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Must-Have Buckle-Strap Sandals
These buckle-strap sandals are a trendy must-have for the spring and summer seasons! They feature a round toe, a two-strap design with adjustable buckles, an open back for easy on-and-off styling, and a flat sole. Style with hoop earrings and a layered necklace.
Fit & Features
- Open round toe
- Two-strap design
- Adjustable buckles
- Open back
- Flat sole
- Faux microsuede material
- Runs true to size
Style Number/Barcode: 07404-1132
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meli Mid-Rise Cuffed Shorts By Windsor Denim
Take your daily walk around town in the Meli shorts by Windsor Denim perfect for adding to your closet! They feature a classic mid-rise waist, distressed accents, and a cuffed hem on white denim fabric. Complete the look in a cute crop top for a backyard bbq or festival!
Fit & Features
- Mid-rise waist
- Distressed accents
- Cuffed hem
- Front button closure
- Five-pocket styling, belt loop accents
- Premium white denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06603-0307
Category Name: Vacation Looks
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fabulous Vibes Platform Mules
Give off fabulous vibes in these of-the-moment platform mules! They feature an open almond-shaped toe, a wide banded toe strap, an open back for easy on-and-off styling, a platform sole, and a thick block heel. Pair with a quilted handbag.
Fit & Features
- Open almond-shaped toe
- Wide banded toe strap
- Open back
- Platform sole
- Thick block heel
- Faux leather material, subtle cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4161
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Eyes on You Knit Striped Mini Dress
Turn heads without even trying. This tube striped dress hugs you just right with a twist-front that brings the drama.
Fit & Features
- Striped pattern, stretchy knit fabric
- Strapless tube sweetheart neckline
- Twist bust
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000044
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leave An Impression Halter Sweater Mini Dress
Leave an impression in this sweater mini dress for dates or weekend getaways! The rib knit dress features a sleeveless halter neckline, a partially open back, a bodycon silhouette, and a mini-length hem with a flirty slit. Complete the look in heeled sandals.
Fit & Features
- Sleeveless halter neckline
- Partially open back
- Bodycon silhouette
- Mini-length hem, slit accent
- Rib-knit sweater fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1424
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chrome Cutie Slide Sandals
Slip into these cute and effortless chrome slide sandals perfect for your everyday occasions! They feature an almond toe, a wide single strap, and a flat sole on faux leather material. Complete the look in a trendy denim jacket.
Fit & Features
- Almond toe
- Wide single strap
- Faux leather material
- Chrome design
- Slide-on and off styling
- Runs true to size
Style Number/Barcode: 07404-1085
Category Name: Vacation Looks
Price: $6.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Alluring Wide-Leg Pants
Entice them all with your alluring look in these bold wide-leg pants! They feature a high-rise banded waist, a hip-hugging fit, and a flowy, relaxed, wide-leg silhouette. The textured knit fabric offers plenty of stretch. Style these chic pants with the matching crop top!
Shop Matching Top: Always Alluring Halter Crop Top
Fit & Features
- High-rise elasticized waist
- Hip-hugging fit
- Flowy, wide-leg silhouette
- Textured knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 06502-2244
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweetest Of All Paisley Crop Top
A paisley crop top that adds boho sweetness to your favorite bottoms!
Fit & Features
- Paisley graphic print, stretchy knit fabric
- Scoop neckline
- Adjustable spaghetti straps
- Fitted pointy crop hem
- Runs true to size
Style Number/Barcode: 06002-000055
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale