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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Sweet Looks V-Neck Lace Babydoll Dress
Sweeten any occasion in this lace babydoll dress with a charming ruffled silhouette and mini-length hem!
Fit & Features
- Lace fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Ruffled babydoll silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000093
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Sun Floral Tie-Front Bikini Top
Enjoy the sweet sunshine at the pool or beach in this floral tie-front bikini top! Pair with the matching bikini bottoms.
Fit & Features
- Floral print, knit lined fabric
- Short puff sleeves
- Tie-front design
- Ruffled trim
- Runs true to size
Shop The Matching Bikini Bottoms: Sweet Sun Floral Bikini Bottoms
Style Number/Barcode: 07104-0726
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laid Back Cutie High-Rise Wide-Leg Pants
Unleash your inner laid back cutie with these high-rise wide-leg pants. The drawstring waist and side pockets provide comfort and convenience, while the flowy gauze woven fabric adds a touch of bohemian charm. Complete the look in a basic crop top for casual plans or travel!
Fit & Features
- Gauze woven fabric, no stretch
- High rise drawstring waist
- Side pockets
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0813
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oh So Sweet Tie Back A-Line Mini Dress
You're going to look so sweet in this A-line mini dress for weekend plans! Featuring cap sleeves, a square neckline, and a tie-back design to turn heads. The A-line silhouette and mini-length hem will have you looking effortlessly chic! Complete the look in platform shoes.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Square neckline
- Tie back design
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5682
Category Name: Vacation Looks
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring 'Fit Plunging Halter Mini Dress
Create an alluring 'fit for sunset drinks in this textured knit mini dress featuring a plunging V-neck with a bust tie accent, halter straps, and a bold open back with a tie-back design. The short, bodycon silhouette will flaunt your gorgeous curves.
Fit & Features
- Sheer textured knit fabric with knit lining, high stretch
- Sleeveless plunging V-neckline, bust tie accent
- Tie-back halter spaghetti straps
- Open back, tie-back spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000020
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Best In Style Halter Button Up Vest
You'll be voted best in style wearing this sleeveless vest perfect for weekend getaways or brunch with the ladies! The vest boasts a chic halter neckline, a partially open back to reveal some skin, button front closures, and a cropped hem to flaunt your cute self. Complete the look in trouser pants and mules for an effortless flair.
Fit & Features
- Twill cotton woven fabric, no stretch
- Halter strap with button closures
- Button front closures
- Faux pockets
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1715
Category Name: Vacation Looks
Price: $15.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Dream Crochet Espadrille Platform Sandals
These boho crochet espadrille platform sandals are a summer dream! They feature an open square-shaped toe, double-banded straps with a cute multi-colored crochet design, an open back for effortless on-and-off styling, and a tall espadrille platform sole and wide block heel. Style with a flowy sundress.
Fit & Features
- 4" Wide block heel
- Espadrille material, faux leather upper
- Open square toe
- Double-banded straps, multi-colored crochet design
- Open back, on-and-off styling
- Platform sole
- Luxe fit cushion insole
- Runs true to size
Style Number/Barcode: 07401-4721
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cabana Honey Tie Front Crochet Crop Sweater
Head to the cabana in this stylish crochet crop sweater perfect for layering over your swimsuit! Featuring long sleeves with flare cuffs for added trendiness, dual tie-front closures, and a cropped hem that flaunts your figure. Complete the look with sunnies.
Fit & Features
- Sheer crochet fabric, no stretch
- Dual tie-front closures
- Cropped hem
- Runs true to size
Style Number/Barcode: 06204-1743
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dose Of Sweetness Bodycon Floral Mini Dress
Ditsy florals add sweetness to this bodycon mini dress you'll adore for casual summer plans! Designed with a sheer eyelet knit fabric with a knit lining, this dress offers plenty of stretch for comfortable wear. It features adjustable spaghetti straps, a sleeveless square neckline with a dainty lace trim, ruching at the bust accented with a mini flower detail, and a flattering bodycon fit with a mini-length hem. Complete the look with earrings and sneakers.
Fit & Features
- Ditsy floral print
- Sheer eyelet knit fabric with knit lining, plenty of stretch
- Adjustable spaghetti straps
- Square neckline, dainty lace trim
- Ruched bust with mini flower detail
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5730
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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By the Shore Starfish Bracelet
Bring a little beachy charm to your stack with this starfish wire bracelet. Dainty yet eye-catching, it’s the perfect piece for layering or rocking solo.
Fit & Features
- Starfish charm insets
- Slim design
- Push-clasp closure
Style Number/Barcode: 07003-000142
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Marvelous Darling Lace-Up Floral Chiffon Dress
This floral chiffon dress is a must-have for any fashionista attending many events this season! With a floral print and ruffled hem, this fit-and-flare dress is both charming and chic. The V-neckline and ruffled straps add a touch of flirty femininity, while the open lace-up back will have everyone love swept, and is finished with a ruffled short-length hem. Complete the look with a ring set and mules!
Fit & Features
- Floral print, chiffon fabric lined with stretchy knit
- Ruffled straps
- Lace-up, back zipper and hook-eye closure
- Fit and flare silhouette
- Ruffled short-length hem
- Sticky bra or pasties recommended
- Runs true to size
Style Number/Barcode: 05101-2962
Category Name: Vacation Looks
Price: $6.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ready To Charm Halter Cutout Wide-Leg Jumpsuit
This sleeveless jumpsuit is ready to charm everyone this season! This jumpsuit features a halter neckline with a tie and strappy cutout back. The wide-leg silhouette adds a touch of breezy style to your look perfect for any occasion! Complete the look in heeled sandals.
Fit & Features
- Sheer woven fabric with woven lining, no stretch
- Halter neckline with tie
- Strappy cutout back
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1415
Category Name: Vacation Looks
Price: $11.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summertime Chic Strappy Espadrille Wedges
Level up your summertime 'fits with these chic strappy espadrille wedges. They feature an on-trend woven espadrille wedge heel, an open square-shaped toe, an asymmetric strappy design across the foot, and thin adjustable ankle and heel straps for a customized fit with a buckle closure. Style with a floral dress for weekend brunch!
Fit & Features
- 4" Espadrille wedge heel
- Faux leather upper
- Open square toe
- Asymmetric strappy design
- Adjustable ankle and heel straps, buckle closure
- Luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07406-0338
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wrap Around The Block Strappy Platform Sandals
Take a stylish walk around the block in these platform sandals featuring a round toe, asymmetrical faux leather strap, and an adjustable ankle strap with buckle closure. Complete the look in a breezy maxi dress for vacation or weekend plans!
Fit & Features
- Round toe
- Asymmetrical faux leather straps
- Platform sole
- Adjustable ankle strap with buckle closure
- Runs true to size
Style Number/Barcode: 07404-1234
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Mood Crochet Cropped Sweater
This cropped sweater is designed with a breezy open crochet knit fabric, creating a bold sheer look perf for weekend getaways. It features a wide boat neckline and long bell sleeves to give off those effortlessly chic vibes. Style with the matching maxi skirt.
Shop Matching Bottoms: Weekend Mood Crochet Maxi Skirt
Fit & Features
- Open crochet knit fabric, minimal stretch
- Boat neckline
- Long bell sleeves
- Cropped hem
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-2113
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Getaway Attitude Off-The-Shoulder Crochet Top
Serve a cute attitude for your next getaway in this off-the-shoulder crochet top. Crafted from sheer crochet knit fabric that brings dreamy vibes, this top features long bell sleeves, a bungee halter strap with beading that creates the front adjustable ruching so you customize the style, and a cropped hem. Complete the look in printed flare pants for a vacay or festival!
Fit & Features
- Sheer crochet knit, bust lining
- Off-the-shoulder
- Bungee halter strap with beading
- Adjustable ruching
- Cropped hem
- Runs true to size
Style Number/Barcode: 06001-5097
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Slay Strapless Cutout Mini Dress
Serve a sultry slay in this curve-hugging mini dress designed with a strapless neckline, ruched detailing, and an open lower back with an O-ring cutout for a trendy allure.
Fit & Features
- Smooth double-lined knit fabric, high stretch
- Strapless straight-across neckline
- Ruching
- Open lower back, O-ring cutout
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-000065
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Match High-Rise Palazzo Pants
Flirt up your style in these palazzo pants on vacation or weekend fun! The high-rise waist and wide-leg silhouette provide a flattering fit, while the flowy design adds a touch of playful charm. Complete the look with the matching top.
Shop Matching Top: Flirty Match Short Sleeve Tie-Front Top
Fit & Features
- Woven fabric, no stretch
- High-rise elasticized waist
- Wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06402-1396
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romantic Icon Retro Heart Sunglasses
Be seen as a romantic icon in these retro heart sunglasses! They feature a heart-shaped design with trim, and tinted lenses to help protect your eyes, metal arms, and nose supports for comfortable wear. Complete the look in a scoop neck bodysuit and denim shorts for a backyard BBQ or summer pool party!
Fit & Features
- Heart-shaped design with trim
- Tinted lenses
- Metal arms
- Nose supports
Style Number/Barcode: 07008-1085
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Perfection Ruffled Floral Chiffon Maxi Skirt
Be gorgeous and perfect all season in this floral chiffon maxi skirt at formal soirees! Made with floral and leaf print chiffon fabric, this skirt is a must-have for any fashion-forward girlie. Its high-rise waist and tiered ruffled silhouette create a flattering fit, while the maxi-length hem adds a chic touch. Complete the look with the matching top.
Shop The Matching Top: Gorgeous Perfection Halter Floral Chiffon Crop Top
Fit & Features
- Floral and leaf print, chiffon fabric lined with stretchy knit
- High-rise waist
- Back zipper and hook-eye closure
- Tiered ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 06401-0685
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Cool Long Sleeve Denim Romper
Capture a casually cool vibe for your weekend plans in this long sleeve denim romper! It features a structured collared neckline, long sleeves with snap button closures, a snap button-down front, dual buttoned chest pockets and side pockets, a stylish cuffed hem, and a relaxed fit for an effortlessly on-trend look. Pair with hoop earrings and sneakers!
Fit & Features
- Non-stretch denim fabric
- Collared neckline
- Long sleeves with snap button closures
- Snap button-down front
- Buttoned chest pockets, side pockets
- Cuffed hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06303-0286
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Blooms Flower Hair Claw Clip
Vacay mode activated! Show off these tropical flower hair claw clips while on your getaway or a chic pool party.
Fit & Features
- Tropical flower
- Claw clip closure
Style Number/Barcode: 07006-000058
Category Name: Vacation Looks
Price: $3.97 $7.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho Aesthetic Strapless Tie Back Paisley Maxi Dress
Channel a boho aesthetic in this paisley maxi dress for carefree summer days! With its strapless neckline and tie-back design, this maxi dress hugs your curves and flows effortlessly with a beautiful paisley print on knit fabric with chiffon lining. Complete the look with earrings for a dressy summer party!
Fit & Features
- Paisley print, knit fabric lined with chiffon
- Strapless neckline
- Tie back design
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3400
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning One Halter V-Neck Ruffle Floral Maxi Dress
You'll take every vacation or summer party by storm when you have this floral maxi dress! This stunning maxi dress features a halter V-neckline with spaghetti strap tassel ties, a stretchy smocked bodice accentuating your figure, and hidden side pockets for added convenience. The flowy ruffled silhouette and floor-length hem add a stylish finish. Complete the look in sandals and sunglasses!
Fit & Features
- Floral print, woven fabric with lining, no stretch
- Halter V-neckline
- Spaghetti strap tassel ties
- Stretchy smocked bodice
- Flowy ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5776
Category Name: Vacation Looks
Price: $9.97 $64.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale