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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Knit Your Average Crochet Sweater Mini Dress
Elevate your look to a subtle shine factor in this crochet sweater mini dress perfect for layering over your bikini on vacation or a private yacht party! It features a sleeveless cowl neckline, halter tie-back straps, a partially open back, and a bodycon fit. The dress is composed of a space dye metallic sheer knit fabric. Style with strappy sandals.
Fit & Features
- Sleeveless cowl neckline
- Halter tie-back straps
- Partially open back
- Bodycon fit
- Mini-length hem
- Space dye metallic sheer knit fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06005-1659
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Basic Perfection Knit Halter Crop Top
This casual ribbed sweater knit crop top is the perfect basic for everyday styling! It features a sleeveless halter neckline with spaghetti straps, an open back with a cross-back strap design, and a fitted cropped hem. The sweater knit fabric offers plenty of stretch. Pair with a mini skirt and mules.
Fit & Features
- Sleeveless halter neckline
- Spaghetti straps
- Open back, cross-back strap design
- Fitted cropped hem
- Ribbed sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1367
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Back To Cool High-Rise Parachute Joggers
Take your street style back to cool in these parachute joggers perfect for adding to your everyday rotation! They feature a high-rise elasticized waist with an adjustable drawcord, hidden side pockets, a relaxed silhouette, and a drawcord hem so you can customize the style. Complete the look in a basic crop tee and sneakers.
Fit & Features
- High-rise elasticized waist
- Adjustable drawcord
- Hidden side pockets
- Relaxed silhouette
- Drawcord hem
- Lightweight nylon fabric, no stretch
- Runs true to size
Style Number/Barcode: 06302-0737
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Glam Vibe Pearl Denim Jacket
This chic pearl denim jacket will give off a trendy glam vibe! It features a collared neckline, fab faux pearl embellishments on the shoulders, long sleeves with button cuffs, a button-down front, chest pockets, and a cropped hem with a relaxed fit. Layer over a fitted bodysuit with matching denim shorts for the coolest look.
Fit & Features
- Collared neckline
- Faux pearl embellishments
- Long sleeves, button cuffs
- Button-down front, dual chest pockets
- Cropped hem, relaxed fit
- Light wash rigid denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06203-0507
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Allure Watercolor Print Bra Top
Showcase a bold allure and draw all the attention in this trendy watercolor-printed bra top. It features a sweetheart neckline with a padded bust and structured underwire for support, long fitted sleeves, and an ultra-cropped fitted hem with a lower back adjustable strap The sheer mesh fabric offers plenty of stretch. Style with high-rise jeans and strappy mules for a fab happy-hour vibe!
Fit & Features
- Sweetheart neckline, padded bust, structured underwire
- Long fitted sleeves
- Ultra-cropped fitted hem
- Lower back adjustable spaghetti strap
- Watercolor print
- Sheer mesh fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4752
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Vibes Sleeveless Scoop Neck Bodysuit
Bring the casual vibes to your everyday 'fits with this sleeveless bodysuit. Featuring a scoop neckline, thin tank shoulder straps, a matching scoop-back design, and a form-hugging fit, this bodysuit can effortlessly be styled for whatever you have planned. The knit fabric features a textured pattern and offers plenty of stretch. Pair with denim shorts and a flowy duster for a cute weekend look.
Fit & Features
- Sleeveless scoop neckline
- Thin tank shoulder straps
- Scoop-back design
- Form-hugging fit
- Knit fabric, textured pattern, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-1550
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Howdy Cutie Straw Cowboy Hat
Everyone will be saying howdy to you looking so cute in this straw cowboy hat at festivals! It features a classic wide and curved brim and an adjustable beaded string. Style with a flirty crochet top and printed pants.
Fit & Features
- Classic wide and curved brim
- Adjustable beaded string
- Cowboy style
- Straw material
Style Number/Barcode: 07302-1372
Category Name: Vacation Looks
Price: $10.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Mood Cutout Bodycon Midi Dress
Keep your summer style sultry and on-trend with this curve-hugging bodycon midi dress. It features a sleeveless square neckline, thin tank shoulder straps, an asymmetric cutout that continues all around the waist with a sleek O-ring accent at the front, and a midi-length hem. The ribbed knit fabric offers plenty of stretch. Pair with strappy heels.
Fit & Features
- Sleeveless square neckline
- Thin tank shoulder straps
- Asymmetric cutout, all around the waist, metal O-ring accent
- Midi-length hem
- Bodycon fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5189
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Nautical Vibes Striped Mini Dress
Elevate your summer style and give off chic nautical vibes in this striped mini dress! It features a sleeveless scoop neckline, spaghetti straps, a faux wrap waist design with a tie-front detail, a mini-length hem, and a form-hugging fit. The stretchy brushed knit fabric features an all-over horizontal striped pattern. Complete the look with espadrille sandals for a beachside brunch!
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Faux wrap waist design, tie-front detail
- Mini-length hem, form-hugging fit
- Horizontal striped print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5067
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Meet Me in the Meadow Chiffon Floral Maxi Dress
Easy, breezy, and made for photoshoots and parties. This strapless chiffon maxi dress with a smocked bodice and floral print gives off-carefree weekend energy with a soft, boho vibe.
Fit & Features
- Floral print, chiffon fabric, short woven lining
- Strapless smocked bodice
- Flowy silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000107
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunshine Girlie Crochet Chevron Sweater Dress
Calling all the sunshine girlies! Slip on this playful crochet chevron sweater dress for backyard pool parties or vacations. It features a sleeveless halter V-neckline, tie-back spaghetti straps, an open back, a bodycon silhouette, and a mini-length hem with ribbed trim. Style with chunky platform heels for a complete look!
Fit & Features
- Sleeveless halter V-neckline
- Tie-back spaghetti straps
- Open back
- Bodycon silhouette
- Mini-length hem with ribbed trim
- Chevron pattern, crochet sweater fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1658
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendsetting Vibes Oversized Square Sunglasses
Show off those trendsetting vibes with these sleek shades! They feature a glam oversized design with a curved square shape, a thin metal frame, chain-link accents on the arms, rubber nose pads for support, and tinted lenses with a cool smokey brown hue. Style with hoop earrings.
Fit & Features
- Oversized design, curved square shape
- Thin metal frame
- Chain-link accents on the arms
- Rubber nose pads
- Smokey brown tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1026
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Step Up Your Style Oversized Square Sunglasses
Step up your summer style with these fab oversized sunglasses. They feature a square-shaped oversized design with a clear plastic frame, metal chain-link accents on the arms with mini rhinestone embellishments, and tinted lenses. Pair with a mini handbag.
Fit & Features
- Oversized square-shaped design
- Clear plastic frame
- Metal chain-link accents on the arms, mini rhinestones
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1027
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cancun Chica Tropical Satin Tie Front Top
You'll be the cutest chica in this tropical satin top in Cancun! It features flowy kimono sleeves, a plunge V-neckline, a cropped hem, and customizable straps that can tie in the front or back. Style with trendy denim shorts and wedges to complete your vacay look!
Fit & Features
- Flowy kimono sleeves
- Plunge V-neckline
- Cropped hem
- Customizable straps
- Tropical print
- Silky satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06204-1585
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Greek Key On Fleek Mesh Ruche Mini Skirt
Look on fleek for vacationing in Greece or on a private yacht in this fab mesh Greek key print mini skirt! It features a high-rise elasticized waistband, bodycon silhouette, and a front ruched drawstring so you can customize the style and a bodycon fit. Style with a crop top and clear heel mules for a fabulous look.
Fit & Features
- High-rise elasticized waistband
- Bodycon silhouette
- Front ruched drawstring
- Mini-length hem
- Greek key print
- Sheer mesh fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06501-0654
Category Name: Vacation Looks
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Let's Get Together Tie-Front Crop Top
You and this crop top must get together soon! Start prepping for brunch under the sun in this sleeveless top featuring a sweetheart neckline, a tie-front design, spaghetti straps, a smocked back panel, and a fitted, cropped hem. Complete the look with the matching maxi skirt!
Shop Matching Bottoms: Let's Get Together Tiered Maxi Skirt
- Sleeveless sweetheart neckline
- Tie-front design
- Spaghetti straps
- Smocked stretchy back panel
- Fitted, cropped hem
- Gauze fabric
- Runs true to size
Style Number/Barcode: 06003-1814
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Mood Ditsy Floral Mini Dress
This adorable ditsy floral mini dress will have you in the mood for easy summer days! It features a sleeveless scoop neckline, a small bust cutout with a tie-front detail, spaghetti straps, a mini-length hem, and a form-hugging silhouette. The ditsy floral printed ribbed knit fabric offers plenty of stretch. Style with hoop earrings and strappy sandals.
Fit & Features
- Sleeveless scoop neckline
- Small bust cutout, tie-front detail
- Spaghetti straps
- Mini-length hem, form-hugging fit
- Ditsy floral print
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5114
Category Name: Vacation Looks
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Floral Vibes Ruched Mini Dress
Capture a sweet romantic look in this flirty floral mini dress! It features a sleeveless V-neckline with ruching at the bust, spaghetti straps, a mini-length hem, and a form-hugging fit. The stretchy ribbed knit fabric features an all-over ditsy floral print for an adorable summer style. Pair with espadrille sandals for a day date.
Fit & Features
- Sleeveless V-neckline
- Ruching at the bust
- Spaghetti straps
- Mini-length hem, form-hugging fit
- Ditsy floral print
- Ribbed knit fabric, smooth knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4760
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Strut Floral Lace-Up Block Heels
Strut into your next party in bold style with these fabulous floral block heels! They feature an open square toe, a clear toe strap, a closed back, a thin lace-up strappy design that wraps around the leg, a sturdy block heel, and an all-over tropical floral print pattern that will catch everyone's attention. Complete the look with hoop earrings and a mini handbag.
Fit & Features
- Open square-shaped toe
- Clear PVC toe strap
- Closed back
- Thin lace-up strappy design
- Block heel
- Tropical floral print
- Runs true to size
Style Number/Barcode: 07401-4427
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Gorgeous Getaway Tropical Print Midi Dress
Get a gorgeous look for your next vacay getaway with this alluring tropical print midi dress. It features a sleeveless square neckline, spaghetti straps, an open back with a cross-back lace-up strappy design, ruching at the waist, a midi-length hem with an asymmetric high side slit, and a curve-hugging silhouette. The all-over palm leaf pattern on the stretchy knit fabric will bring those tropical vacation vibes. Style with cute wedges.
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Open back, cross-back lace-up strappy design, tie closure
- Ruched detailing at the waist
- Midi-length hem, asymmetric high side slit
- Curve-hugging silhouette
- Tropical palm leaf print, knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5008
Category Name: Vacation Looks
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Time To Escape Tropical Print Maxi Dress
Get ready to escape on a gorgeous getaway in this sultry tropical print maxi dress! It features a sleeveless asymmetric one-shoulder neckline with a spaghetti strap, a bold and alluring asymmetric waist cutout with a trendy O-ring accent, a hip-hugging fit that will hug your natural curves, and a floor-length hem with a thigh-high side slit to showcase some leg. The all-over palm leaf print on the stretchy knit fabric captures those tropical oasis vibes. Style with strappy sandals.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Single adjustable spaghetti strap
- Asymmetric waist cutout, O-ring accent
- Hip-hugging fit, floor-length hem, high side slit
- Tropical palm leaf print
- Knit fabric, mini-length lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5016
Category Name: Vacation Looks
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Style Refresh Low Block Heel Mules
These chic low block heel mules are a fab style refresh! They feature an open square toe, a wide banded strap, an open back for easy on-and-off styling, and a low block heel. Complete your look with chunky hoop earrings and a mini handbag.
Fit & Features
- Open square-shaped toe
- Wide banded toe strap
- Open back, on-and-off styling
- Low block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4223
Category Name: Vacation Looks
Price: $12.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fresh Summer Vibes Wrap-Front Romper
Show off a fresh summer vibe in this elevated and chic woven romper. It features a sleeveless V-neckline, tank shoulder straps that lead to an open back with a cross-back lace-up design, a lower back cutout, a flattering high waist seam, a ruched wrap-front design with a short skirt overlay, and fitted shorts. Style with espadrille wedges for a cute daytime party look.
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Open back, cross-back lace-up design, tie closure
- Lower back cutout, zipper and hook-eye closure
- High waist seam, ruched wrap-front, short skirt overlay, fitted shorts
- Lined smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06403-0330
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Desert Dreamer Crochet Lace Kimono
Channel those dreamy boho vibes in this gorgeously detailed crochet lace kimono. The long relaxed fit is perfect for a desert music festival.
Fit & Features
- Sheer crochet lace fabric
- Half-length loose sleeves
- Open front
- Long-length hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06204-2068
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free