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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Sparkle Toes Rhinestone Mules
Sparkle down to your toes in these dressy stiletto mules designed with an on-trend, square toe, PVC strap with rhinestone mesh and a twist accent, and a faux leather footbed. Complete your formal look in a party dress.
Fit & Features
- Square toe
- Stiletto heel
- PVC strap, rhinestone mesh, twist accent
- Faux leather footbed
- Runs true to size
Style Number/Barcode: 07401-4078
Category Name: Vacation Looks
Price: $15.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Butterfly Charm Choker Set
Sweet and whimsy! Create a dreamy boho glam look with this two-pack choker set featuring one rhinestone choker and one butterfly charm choker each with a lobster clasp closure. Complete your dressy look with chic earrings.
Fit & Features
- Two-pack choker set
- One rhinestone choker
- One butterfly charm choker
- Each with a lobster clasp closure
Style Number/Barcode: 07002-1271
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Taylor High-Rise Skinny Ankle Jeans by Windsor Denim
This pair of Taylor skinny jeans by Windsor Denim will be a closet staple. They feature a high-rise waist, destructed detailing down the front, and a classic skinny leg fit. The denim fabric offers a moderate stretch for comfortable wear. Style with a crop top and mules.
Fit & Features
- High-rise waist
- Destructed detailing
- Skinny leg fit
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06602-0359
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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New Places High Rise Flare Denim Jeans
Wear these denim jeans to new places! They feature a flattering, high-rise waist and form-fitting hips, distressed knee accents, and a flared hem on vintage-inspired medium wash non-stretch denim fabric. Complete your trendy look in a bodysuit.
Fit & Features
- High-rise waist
- Form-fitting hips
- Distressed knee accents, flared hem
- Front button and hidden zipper closure
- Five-pocket styling, belt loop accents
- Medium wash non-stretch denim
- Fits true to size
Style Number/Barcode: 06602-0388
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Peek Dainty Layered Necklace
Give your outfit a chic peek of glam with this dainty layered necklace design with five lariat-styled layers, clear stone charms, and a lobster clasp closure. Complete the look in a low-cut long dress and clutch.
Fit & Features
- Five-lariat styled layers
- Clear stone charms
- Lobster clasp closure
- Dainty chain-links
Style Number/Barcode: 07002-1274
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Muse Layered Body Chain
You'll be a trendy muse when you accessorize with this dainty body chain! It features a layered design with a twisted chain and coin charms in a drop design. Style with your fave crop top and a chic mini skirt.
Fit & Features
- Layered body chain
- Twisted chain
- Coin charms, drop design
Style Number/Barcode: 07002-1265
Category Name: Vacation Looks
Price: $5.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vineyard Chic Cork Lace-Up Heels
Grab the girls and these cork block heels for a day-out wine tasting! They feature an almond toe, braid toe strap, and a lace-up tie closure. Complete the look in a breezy jumpsuit.
Fit & Features
- Almond toe
- Block heel
- Braid toe strap
- Lace-up tie closure
- Runs true to size
Style Number/Barcode: 07401-4080
Category Name: Vacation Looks
Price: $5.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Aloha Babe Flower Graphic Crop Tee
Whether you're on vacay or just hanging out, this flower graphic crop tee adds a cute look to your favorite bottoms.
Fit & Features
- Cotton knit stretchy fabric
- Short sleeves
- Crew neckline
- Flower graphic
- Relaxed fit
- Crop hem
- Runs true to size
Style Number/Barcode: 06002-000051
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Glow Rhine Layered Choker
Unleash your summer glow and adorn your outfit with this choker necklace featuring a three-layered design, one rhinestone row, one snake chain row, one chainlink row, and a lobster clasp closure. Complete the look in a denim romper.
Fit & Features
- Three-layered design choker
- One rhinestone row
- One snake chain row
- One chainlink row
- Lobster clasp closure
Style Number/Barcode: 07002-1239
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take Note V-Neck Sweater Dress
Everyone will take note of how sultry this sweater dress is on you! It features a sleeveless, v-neck, cutout bodice with wrap tie-back closure, side slit accent, and a midi, curve-hugging silhouette. Complete the look in chic strappy heels for a daytime soiree.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, v-neck, tank-style straps
- Cutout bodice
- Wrap tie-back closure
- Side slit accent
- Midi, curve-hugging silhouette
- Sweater rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1488
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make It Chic Tube Top
This strapless tube top moment hugs you just right with ruched details for that elevated off-duty model look.
Fit & Features
- Smooth knit fabric with subtle sheen
- Strapless tube folded neckline
- Ruched details
- Fitted hem
- Runs true to size
Style Number/Barcode: 06001-000528
Category Name: Vacation Looks
Price: $24.90
Availability: In Stock
Available Color: RED, MAGENTA
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Always Trendy Lace-Up Tank Top
Always trendy and a staple! This sleeveless tank top adds the perfect eye-catching style to your everyday fit. It features a V-neck, thin shoulder straps, and a trio of lace-up plackets along the cropped hem on stretchy, rib-knit fabric. Complete the look in flare pants for a summer carnival.
Fit & Features
- Sleeveless, V-neck, thin shoulder straps
- Three lace-up plackets
- Cropped hem
- Stretchy rib-knit fabric
- Runs true to size
Style Number/Barcode: 06002-1339
Category Name: Vacation Looks
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Biker Babe Cropped Graphic Tee
Bring the cool girl energy with this edgy graphic tee! It features a crew neckline, short sleeves, a center motorcycle graphic with the script "American Motorcycle Legend," front slashed detailing, and a cropped, form-hugging fit. Style with high-rise distressed denim.
Fit & Features
- Crew neckline, short sleeves
- Motorcycle graphic
- Script that reads "American Motorcycle Legend"
- Front slashed detailing
- Cropped, form-hugging fit
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1288
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Glitzy Metallic Bow Sandals
Bring the glitz and glamour with these dressy metallic slide-on sandals. They feature an open square-shaped toe, a wide pleated toe strap with a bow accent, and a flat sole. Style with a wide-leg jumpsuit and a clutch.
Fit & Features
- Open square-shaped toe
- Wide pleated toe strap
- Bow accent
- Flat sole
- Metallic finish
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1075
Category Name: Vacation Looks
Price: $14.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Swirls V-Neck Mini Dress
Perfectly swirled and smoothed to perfection! Showcase a head-turning look in this sleeveless mini dress featuring a v-neck, bungee spaghetti straps, bodycon silhouette, slit accent, and a marble print on brushed knit fabric. Complete the look in lace-up heels for a summer party.
Fit & Features
- Sleeveless, v-neck, bungee spaghetti straps
- Bodycon silhouette
- Slit accent
- Mini-length hem
- Marble print
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4660
Category Name: Vacation Looks
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Speedster Racing Graphic Crop Top
Show off your need for speed with a graphic crop top that brings the heat! The top features a crew neckline, short sleeves, an asymmetrical slit paired with safety pins, and an image of a racecar with "Speed Racing" text above the car. The crop top is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with pleather shorts and combat booties for an edgy outfit.
Fit & Features
- Crew neckline
- Short sleeves
- Asymmetrical slit, safety pins
- Racecar image, "Speed Racer" text
- Cropped hem
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1397
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Real Cute Off The Shoulder Top
You'll look real cute showing some shoulder. This crop top features long sleeves, a halter tie neckline, an off-the-shoulder bodice, and a front ruched design on soft and stretchy knit fabric. Complete the look in a midi skirt and sandals.
Fit & Features
- Long sleeves
- Halter tie neckline
- Off-the-shoulder bodice
- Front ruched design
- Cropped hem
- Soft and stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06001-4387
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Basic One-Shoulder Crop Top
This sleek basic crop top will step up your everyday style. It features a sleeveless one-shoulder neckline with an asymmetrical tank strap, a cropped, form-hugging fit, and is composed of a stretchy ribbed sweater knit fabric. Pair this top with cutoff denim shorts and slides.
Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetrical tank strap
- Cropped, form-hugging fit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1506
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mid Rise Straight Leg Denim Jeans
Kick your street style up a notch in these denim jeans featuring a flattering mid-rise asymmetrical waist, straight-leg silhouette, and vintage-inspired medium wash denim fabric with a light color fading. Complete the look with a crop top and mules.
Fit & Features
- Mid-rise asymmetrical waist
- Straight-leg silhouette
- Five-button fly closures
- Belt loop accents
- Five-pocket styling
- Medium wash non-stretch denim, light color fade
- Runs small, please size up
Style Number/Barcode: 06602-0386
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Desert Explorer Graphic Crop Top
Step up your rocker-chic look with this cool graphic crop top. It features a sleeveless halter neckline with a sleek O-ring accent and chain-link straps, a center eagle and desert background graphic with the script "Desert Explorer, Feel The Sunset," and a cropped, form-hugging fit. Style with distressed denim and combat boots.
Fit & Features
- Sleeveless halter neckline
- O-ring accent, chain-link straps, adjustable lobster clasp closure
- Eagle and desert background graphic
- Script that reads "Desert Explorer, Feel The Sunset"
- Cropped, form-hugging fit
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1375
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stay Glam Crochet Handbag
Keep your summer look oh-so-glam with this glitzy crochet handbag. It features a tote design with wooden O-ring handles and an included sequin embroidered pouch to store all your essentials in. Style with a mini dress and espadrille sandals.
Fit & Features
- Crochet bag
- Tote design
- Wooden O-ring handles
- Sequin embroidered pouch, top zipper closure
Style Number/Barcode: 07203-1088
Category Name: Vacation Looks
Price: $8.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She Came to Slay Floral Corset Tube Top
When your outfit speaks before you do. This abstract floral tube top brings the drama with corset vibes and a flawless, sculpted fit made for rooftop nights and flirty first dates.
Shop Matching Bottoms: She Came to Slay Floral Maxi Skirt
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract floral print
- Strapless straight-across neckline
- Flexible boning
- Back hook-eye closures
- Fitted, curved, mid-length hem
- Runs true to size
Style Number/Barcode: 06001-000142
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Beauty Cutout Midi Skirt
Showcase your beauty on a sunset stroll in this alluring midi skirt. It features a high-rise waist with a strappy cutout design, a midi-length, curve-hugging fit, and a chic side slit accent. Style with the matching crop top for the perfect look.
Shop Matching Top: Sunset Beauty Halter Crop Top
Fit & Features
- High-rise waist, strappy cutout design
- Midi-length hem, form-fitting silhouette
- Side slit
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06501-0714
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sunset Beauty Halter Crop Top
Showcase your beauty on a sunset stroll in this alluring crop top. It features an off-the-shoulder neckline with short fitted sleeves and thin halter straps, a cinched accent at the bust, a tie-back design, and a cropped, form-hugging fit. Style with the matching midi skirt for the perfect look.
Shop Matching Bottoms: Sunset Beauty Cutout Midi Skirt
Fit & Features
- Off-the-shoulder neckline
- Short fitted sleeves, thin halter straps
- Cinched accent at the bust
- Tie-back design
- Cropped, form-hugging fit
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1594
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance