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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All Ties On You Swimsuit
All eyes will be on you in this tie front swimsuit! It features a deep neckline accented with a tie front and a small keyhole cut out, thin adjustable straps that lead to a sexy back cut out, and a partial coverage bottom. The ribbed one piece is in a perfect rust hue.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small.Style Number/Barcode: 07109-0038
Category Name: Vacation Looks
Price: $14.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Eyes On Me Swimsuit
All eyes are gonna be on you at the beach when you rock this vibrant monokini! It has a V neckline that ties at the bust, adjustable shoulder straps, a hook back closure, a large waist cut out, and a high cut bottom that offers a partial coverage. Bust is not padded.RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.
Model is 5'7 with a 32" bust, 24" waist and 37" hips. She is wearing a size small. ,,Featured in our 2018 Swim Lookbook
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Style Number/Barcode: 07105-0289
Category Name: Vacation Looks
Price: $38.90
Availability: Out of Stock
Product Badge:- Ships Free
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Solid Stunner Ruched Tube Dress
We'll keep it brief: this mini is made for for your next night out! Tube-style dress features a curve-hugging cut, strapless neckline, and all-over strategic ruching detail. Don't forget to pair it with the matching duster! Dress slips on and is made from a smooth, solid woven material with moderate stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05103-0165
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Here To Stay Short Sleeve Tie Front Crop Top
This short sleeve crop top is here to stay in your weekly lineup! Its dual tie front closures and cropped hem add a playful touch, while the scoop neckline with contrast trim and stretchy rib knit fabric provides a flattering fit. Complete the look in high-rise jeans and sandals!
Fit & Features
- Stretchy rib knit fabric
- Contrast trim scoop neckline
- Dual tie-front closures
- Cropped length
- Runs true to size
Style Number/Barcode: 06202-0470
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Miss Midi Striped Dress
Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This red toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch.
Style Number/Barcode: 05102-3994
Category Name: Vacation Looks
Price: $9.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plus Thrill Of Knit Ribbed Dress
Toe the perfect line between casually chic and sultry-on-trend in this off-the-shoulder mini. Dress features all-over medium-width ribbing, a scoop neck, decorative wood-like buttons and a full lining. Dress is made from a soft, heavier-weight cotton blend with a fair amount of stretch.
Style Number/Barcode: 15102-0035
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruffle Ride Skater Dress
Keep it cool in this breezy-beautiful skater dress! It features adjustable spaghetti straps, a seamed V neck bodice, tiers of ruffle trim at the bust, waist, thigh and hem, and an A-line skirt with back zip. Dress is fully lined and made from a lightweight Tencel-blend with natural crinkle-effect and little to no stretch.
Style Number/Barcode: 05102-0329
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bask In The Sun Mini Dress
Brighten up the day in this mini dress! It features a sleeveless bodice, tank-like shoulder straps, a square neck and back, and a short, form hugging fit. The dress is composed of a soft knit fabric that offers plenty of stretch.
Style Number/Barcode: 05102-0098
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tropical Paradise Lattice Romper
Escape to an island paradise in this season ready romper! It features a sleeveless bodice, a plunging V neckline with a lattice accent and an open back design. The slim fit bodice leads to a pair of flowy wide leg shorts. The all over palm leaf print features green and teal hues. Romper is composed of a lightweight woven fabric that offers a relaxed fit with a minimal stretch.Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06303-0029
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Total Tropics Tie Waist Pants
Feel the island vibes in bold, after-dark florals! These elegant bubble crepe pants have a relaxed fit and feature an elasticized waist with front tie and a wide leg. Top is made from a lightweight, lightly textured woven material with a touch of stretch. Don't forget to pair it with the matching ruffle crop top!Style Number/Barcode: 06302-0047
Category Name: Vacation Looks
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smocked In Florals Mini Skirt
Make it a smocked look in florals! The mini skirt features a high rise waist, an all over floral print and a ruffled hem. Skirt is composed of a smocked fabric that offers a relaxed fit with a moderate stretch. Be sure to pick up the matching top to complete your look!Style Number/Barcode: 06301-0029
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffled And Striped Romper
Showcase just how adorable you are in this ruffled and striped romper. It features an off the shoulder sweetheart neckline with a ruffle popover, a high waist seam, an exposed back zipper closure, a cute tie front belt, and fitted shorts. The romper is composed of a woven fabric with no stretch and includes a full knit lining.Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06403-1044
Category Name: Vacation Looks
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Mini Bouquet Kimono Sleeve Romper
As comfy as your fave loungewear and as cute as your club gear, this romper marries the best of both worlds. Romper features an all-over ditsy floral print, kimono-style sleeves, a deep V neck, pleat detail at front, banding at waist, and high-rise shorts. Romper is made from an ultra-soft woven material with moderate stretch.Model is 5'3" with a 32' bust, 22.5" waist, and 34" hips. She is wearing a size small.
Style Number/Barcode: 06503-0037
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sunshine So Fine Wide Leg Pants
Look oh so fine in the summer sunshine with these adorable wide leg pants! They feature a high rise waist, a tie front accent, flowy wide pant legs, and a woven fabric with a full knit lining. The bottoms showcase a pretty all over floral print to bring out those summer vibes. Don't forget to purchase the matching crop top!Model is 5'6.5" with 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06302-0045
Category Name: Vacation Looks
Price: $4.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leafy Greens Printed Slit Pants
Channel only the chicest of nature vibes in these warm weather-ready printed slit pants. They feature a wide-leg silhouette, a shorts-style underlay lining, and high slits at either side. Pants are made from a lightweight rayon material with little to no stretch. Don't forget to pair them with the matching crop top!Style Number/Barcode: 06402-0065
Category Name: Vacation Looks
Price: $4.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Later Skater Floral Combo Romper
Elevate the combo concept with this fluid floral dress-and-romper hybrid! It features an off-the-shoulder neckline, slim banded waist, and A-line skirt with rounded hem and coordinating floral short underlay. Romper slips on and is made from a smooth, woven material with moderate stretch.Model is 5'3" with a 32' bust, 22.5" waist, and 34" hips. she is wearing a size small.
Style Number/Barcode: 06503-0035
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Island Time Floral Skirt
A graphic pink and orange floral set against a rich navy background makes this maxi especially eye catching. Skirt features an elasticized back waist, a partial side zip, and two front slits on either side. Be sure and grab the matching crop top to channel the perfect island vibe! Skirt is unlined and made from a lightweight woven material with little to no stretch.Style Number/Barcode: 06301-0028
Category Name: Vacation Looks
Price: $4.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cutest Of All Ribbon Bow Bodycon Mini Dress
You'll be the cutest of all in this bodycon mini dress out on dates or brunch! Crafted from a woven fabric lined with stretchy knit, this dress features a flattering square neckline and a satin ribbon bow that adds an elegant touch. The bodycon silhouette hugs your curves beautifully, while the mini-length hem gives a playful and flirty vibe. Complete the look in sandals and sunnies!
Fit & Features
- Woven fabric lined with stretchy knit
- Square neckline
- Satin ribbon bow
- Back zipper and hook-eye closure
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5655
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Eve High Waist Cut Off Jean Shorts
Oasis by Eunina
These cut off jean shorts are a must-have for this spring season! They feature a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, subtle distressed detailing, and a raw cut hem. The medium wash jean shorts are composed of a denim fabric that offers moderate stretch and a form-fitting style.
Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.Style Number/Barcode: 06603-0745
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Clara High-Rise Skinny Jeans
Oasis by Eunina
These high-rise cropped skinny jeans are a staple that needs to be in your closet! They feature a high-rise waist, a skinny leg fit, trendy slits at the knees, and a frayed and cropped hem. The jeans are composed of a black denim fabric that offers a moderate stretch and a form-fitting style. Complete the look with a basic bodysuit and clear mules.
Fit & Features
- High-rise waist
- Skinny leg fit
- Slit detailing at the knees
- Frayed ankle-cut hem
- Denim fabric, moderate stretch, form-hugging fit
- Traditional five-pocket and belt loop design
- Front button and hidden zipper closure
Style Number/Barcode: 06602-1682
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hibiscus High Low Crepe Romper
Think classic island style with a distinctly modern twist: this romper features a fitted bodice with off-the-shoulder neckline, micro sleeves, and a gently pleated high-low skirt with shorts-style bottom underneath. Romper is made form a mid-weight crepe fabric with moderate stretch.
Style Number/Barcode: 06503-0041
Category Name: Vacation Looks
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fluttery Feels Striped Jumpsuit
You give us all the fluttery feels baby girl! This adorable blue and white jumpsuit features an off the shoulder bodice with a fun fluttery pop over detail, a tie waistline to give the illusion of 2 pieces, and long, wide, striped pant legs. Jumpsuit is made from a lightweight, cotton-like material with little to no stretch.Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06302-0033
Category Name: Vacation Looks
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Finer Lines Printed Slit Pants
A delicate stenciled print lends these ivory and pink pants their warm weather-ready chic. Pants feature an elasticized back waist, higher rise, and wide legs with slits at either side Don't forget to pair it with the matching tie-front crop! Pants are lined and made from a lightweight Rayon with a bit of stretch at the back.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06402-0031
Category Name: Vacation Looks
Price: $4.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boho Flow Tiered Maxi Skirt
Feel the flow in this low-key chic tiered maxi! A-line skirt features a smocked elasticized waist and three tiers of ruffles. Pair it with the matching crop top for maximum groove! Skirt is lined, slips on, and is made from a lightweight woven material with stretch in the waist.Style Number/Barcode: 06301-0017
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale