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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Keep It Sweet Tie-Strap Eyelet Mini Dress
Keep your summer date outfit sweet with the cutest eyelet mini dress! Designed with a lightweight eyelet knit fabric, this adorable short dress will bring the charm. It features a sleeveless square neckline with ruching at the bust, tie-shoulder straps, and a bodycon silhouette with a mini-length hem to flaunt your figure. Style with sneakers for a casual look or mules for a dressier vibe!
Fit & Features
- Sheer eyelet knit fabric with knit lining
- Moderate stretch
- Ruched square neckline
- Tie-shoulder straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5452
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Looking Good Sweetheart Tie Front Crop Top
Looking good will be effortless in this crop top perfect for vacation or a hot night out! Made of smocked stretchy knit fabric, this top offers comfort and a flattering silhouette. The sweetheart neckline and cropped hem will flatter your figure, while the tie-front adds a touch of flare to your outfit. Complete the look with the matching bottoms.
Shop Matching Bottoms: Looking Good V-Waist Smocked Flare Pants
Fit & Features
- Stretchy smocked knit fabric
- Spaghetti straps
- Sweetheart neckline
- Tie-front
- Cropped length
- Runs true to size
Style Number/Barcode: 06001-5225
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Instant Attitude Cat Eye Sunglasses
Serving vintage vibes with a modern edge, these sunnies bring instant attitude. The sharp cat eye frame and sleek metal finish make them the ultimate cool-girl staple.
Fit & Features
- Cat eye frame
- Tinted lenses
- Rubber nose supports
- Sleek arms with trim
- 100% UV protection
Style Number/Barcode: 07008-000038
Category Name: Vacation Looks
Price: $10.90
Availability: In Stock
Available Color: GOLD
Available Size: NS
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Looking Fly Butterfly Chain Belt
Look fly in this adorable butterfly chain belt! Complete the look in a bodycon midi dress and sandals.
Fit & Features
- Butterfly chain belt
- Lobster clasp closure
Style Number/Barcode: 07301-1159
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Beauty Mesh Strapless Corset Mini Dress
Showcase your beauty at spring and summer parties in this strapless corset mini dress! Designed with a lightweight sheer mesh fabric with a lining for coverage, the dress offers an airy, effortlessly chic vibe. It features a strapless straight-across neckline, a corset-style bodice for a snatched silhouette, and an asymmetric mini-length hem with a flowy A-line fit you'll love. Style with hoop earrings and a layered necklace.
Fit & Features
- Sheer mesh fabric, knit lining, stretchy
- Strapless straight neckline
- Corset flexible boning bodice, back zipper hook-eye closure
- Asymmetric hem
- A-line fit
- Runs true to size
Style Number/Barcode: 05101-3337
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetheart Vibes Strappy Back Floral Crop Top
Get ready for those sweetheart vibes in this strappy floral crop top! This playful top features puff short sleeves and a plunge V-neckline for a flirty touch. The strappy open back with tie closure adds a unique and charming detail, while the cropped hem and rose print fabric make it perfect for any summer occasion. Complete the look with denim jeans.
Fit & Features
- Rose floral print
- Double-lined stretchy knit fabric
- Plunge V-neckline
- Strappy back, tie closure
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5187
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fall For Me Patent Faux Leather Wedges
Fall for these patent faux leather wedges perfect for any occasion! Designed with a sleek almond toe, a wedge heel for comfort and elevated style, and a closed ankle with an adjustable ankle strap allows for a perfect fit. Complete the look with a trending handbag.
Fit & Features
- 4" Wedge heel
- Patent faux leather material
- Adjustable ankle strap with buckle closure
- Almond toe
- Runs true to size
Style Number/Barcode: 07406-0350
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Beauty High Rise Floral Mini Skirt
Effortlessly embody beauty in this floral mini skirt perfect for spring or summer! The high-rise waist and bodycon fit hug your curves, while the ruched seam and slit add a touch of playfulness to the mini-length hem. Complete the look in a crop top.
Fit & Features
- Ditsy floral print, stretchy knit fabric
- High-rise waist
- Ruched seam and slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06501-1012
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beauty So Unique Lace-Up Floral Chiffon Maxi Dress
Give off undeniable grace and beauty in this floral chiffon maxi dress on vacation or at parties! Featuring delicate adjustable spaghetti straps, a V-neckline, and a stunning lace-up back, this dress will accentuate your curves and create a flattering silhouette with a front slit and maxi-length hem. Complete the look in heeled sandals and earrings!
Fit & Features
- Floral print, chiffon fabric, stretchy knit lining
- Adjustable spaghetti straps
- V-neckline
- Lace-up back, zipper and hook-eye closure
- Front slit
- Maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3389
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flawless Floral Kimono Tie-Front Satin Crop Top
You can't go wrong stepping out in this floral satin kimono tie-front top on a getaway or having a sunset dinner! Show off your fashion sense with this crop top with stunning three-quarter length kimono sleeves, tie-front detail, and a dainty floral print. Complete the look with the matching bottoms.
Shop Matching Bottoms: Flawless Floral High Rise Wide-Leg Satin Pants
Fit & Features
- Dainty floral print, satin fabric, no stretch
- Tie-front
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1751
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Mode Espadrille Platform Wedge Heels
Capture the effortlessly chic vibe of the summer season with these espadrille platform wedge heels! They feature an open almond-shaped toe with a wide toe strap, a thin adjustable ankle strap with a buckle closure, a closed back with a woven design, and a tall platform wedge heel for a beachy boho look. Style with a pearl necklace and hoop earrings.
Fit & Features
- 5" Platform wedge heel
- Espadrille material
- Open almond toe, wide toe strap
- Thin adjustable ankle strap with buckle
- Closed back with woven design
- Faux leather luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07406-0347
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Mood Cutout Bodycon Midi Dress
Boost your sultriness in this bodycon midi dress with a flirty cutout back and side slit giving effortless allure!
Fit & Features
- Textured knit stretchy fabric, sewn-in knit lining
- Scoop neckline
- Spaghetti straps
- Cutout back, twist straps
- Bodycon silhouette
- Side slit, midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000083
Category Name: Vacation Looks
Price: $42.90
Availability: In Stock
Available Color: BRONZE
Available Size: XS, S, M, L
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Gorgeous Allure Ruched Chiffon Bra Top
Radiate your gorgeous allure in this sultry ruched chiffon bra top! Designed with an airy sheer chiffon fabric with a front knit lining for coverage, this bra top is perfect for looking sunkissed this season. It features a sleeveless subtle sweetheart neckline, ruching at the bust with padding for support, and adjustable spaghetti straps for a customized fit. The smocked back design offers added stretch, while the ultra-cropped fitted hem creates a snatched silhouette. Complete the look with the matching palazzo pants!
Shop Matching Bottoms: Gorgeous Allure Chiffon Palazzo Pants
Fit & Features
- Sheer chiffon fabric, front knit lining
- Sweetheart neckline
- Ruched bust, padding
- Adjustable spaghetti straps
- Stretchy smocked back
- Ultra-cropped hem, form-hugging fit
- Runs true to size
Style Number/Barcode: 06003-2537
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Vibes Woven Wide-Leg Pants
These airy woven wide-leg pants will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric, they feature a flattering high-rise elasticized waist, front pockets, and a flowy wide-leg silhouette. Style with the matching crop top for a fabulous 'fit!
Shop Matching Top: Sunny Vibes Bow Back Woven Crop Top
Fit & Features
- Woven fabric with minimal stretch
- High-rise elasticized waistband
- Wide-leg fit
- Dual front pockets
- Runs true to size
Style Number/Barcode: 06402-1365
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cascading Romance Ruffle Floral Skater Dress
Get swept away into a world of romance in this floral skater dress perfect for a shower or date! The square neckline and tie-shoulder spaghetti straps add a touch of sweetness, while the stretchy smocked bodice ensures a comfortable fit. The skater silhouette and tiered ruffled hem make this dress perfect for twirling the night away. Complete the look with earrings.
Fit & Features
- Floral print, chiffon fabric with woven skirt lining
- Square neckline
- Tie-shoulder spaghetti straps
- Stretchy smocked bodice
- Skater silhouette with ruffles
- Runs true to size
Style Number/Barcode: 05101-2994
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adorable Allure Puff Sleeve Tie-Back Crop Top
Showcase an adorable allure in the cutest puff sleeve crop top for casual summer parties! Designed with a stretchy knit fabric, it features a plunging V-neckline and short puff sleeves with elastic cinched hems. The trendy open back is accented with scrunched cross-back straps and lower tie-back straps for a customized fit, leading to a fitted cropped hem. Style with high-rise jeans and sneakers.
Fit & Features
- Stretchy double-lined knit fabric
- Plunge V-neckline
- Short puff sleeves
- Open back, cross-back straps, lower tie-back straps
- Fitted elasticized cropped hem
- Runs true to size
Style Number/Barcode: 06001-5186
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Country Babe Colored Stone Straw Cowboy Hat
A distressed cowboy hat featuring trendy colored stones along a string tie, perforated design, and a wide brim to help shade from the sun. Perfect for styling with cowboy boots.
Fit & Features
- Colored stones along the string tie
- Perforated design
- Wide brim
- Adjustable inner strings
- Distressed straw material
Style Number/Barcode: 07302-1641
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Daze Straw Crossbody Bag
Embrace sunnier days in this summer-ready straw crossbody bag featuring an adjustable chain-link strap, a top flap with snap closure, and a spacious lined interior with a single pocket. Complete the look in a cute bikini set for strolling the beaches.
Fit & Features
- Adjustable chain-link strap
- Straw material
- Top flap with snap closure
- Spacious lined interior with a pocket
Style Number/Barcode: 07203-1069
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Leafy Greens Charm Hoop Earrings
Eat your greens. Dress up your look in these dangle leaf charm earrings featuring a large sleek hoop and a fish hook with a rubber-back stopper for a secure fit. Style with a boho-inspired dress for the music festival season!
Fit & Features
- Dangling leaf charms
- Large sleek hoop
- Fishhook, rubber-back stopper
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1281
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hello Summer V-Cut Bikini Bottoms
Say hello to summer in these trendy bikini bottoms featuring a V-cut waist, scrunched detailing at the back, and a thong fit. Pair with the matching bikini top for a pool party.
Shop Matching Top: Hello Summer Triangle Bikini Top
Fit & Features
- Nylon-blend fabric, high stretch
- V-cut waist
- Scrunched back
- Thong fit
- Runs true to size
- Returns are not accepted without the hygienic liner
Style Number/Barcode: 07105-000011
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Muse Linen Thong Wedges
These chic linen thong wedges will radiate bold summer vibes! Designed with a woven linen material, these heels are perfect for your getaway vacays. They feature a tall wedge heel for comfortable wear, a trendy square-shaped toe, a criss-cross thong strap design, and an open back for easy on-and-off styling. Pair with a flowy maxi dress and your fave shades.
Fit & Features
- 4.5" Wedge heel
- Open square toe
- Criss-cross thong strap design
- Open back
- Linen material, faux leather insole
- Runs true to size
Style Number/Barcode: 07406-0345
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flutter Some Hearts Butterfly Charm Earrings
You'll def flutter some hearts in these adorable butterfly charm earrings! Featuring a cascading drop design with rhinestone embellishments, these earrings couldn't get any more whimsical. Pair with a flirty skater dress and some sleek stilettos for your next party.
Fit & Features- Linear dainty drop design
- Rhinestone embellished butterfly charm
- Post back closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.Style Number/Barcode: 07001-0435
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fashionable Good Time Espadrille Flat Sandals
Make sure to pack these espadrille flat sandals to ensure you have a fashionable good time on your next getaway! Featuring a closed round toe and adjustable ankle strap, these sandals offer a comfortable fit. The flat sole and cushioned faux leather insole make these shoes perfect for all-day wear. Complete the look with a trendy crossbody bag.
Fit & Features
- Closed round toe
- Adjustable ankle strap, buckle closure
- Flat sole
- Faux leather cushioned insole
- Espadrille material
- Runs true to size
Style Number/Barcode: 07405-0076
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Infinite Possibilities Tie Front Crop Top
Take the stress out of styling an outfit with this breezy crop top! Designed from a woven fabric, this top features adorable ruffled short sleeves and a flirty tie-front design that flaunts your figure along with the cropped hem. Complete the look with denim shorts and cute sandals!
Fit & Features
- Airy woven fabric, no stretch
- Ruffled short sleeves
- Tie-front closure
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1853
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale