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 Rosey Slip Midi Dress
Keep it rosey in this cute slip dress that keeps your look effortlessly pretty! Step out this season in a slip dress that features a pretty floral print, a high side slit and a midi length silhouette. Complete your look with clear heels and fringe earrings.
Fit & Features
- Plunging v-neckline
- Adjustable spaghetti straps
- Floral print
- High side slit
- Midi length silhouette
- Lightweight woven fabric
- Relaxed fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0836
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Babe Spaghetti Strap Bodysuit
You'll be a total babe in this adorable floral spaghetti strap bodysuit! Featuring a wrap front detail and a gorgeous all over floral print, pair this bodysuit with some mom jeans and a chic handbag for a cute day date look.
Fit & Features
- Adjustable spaghetti straps
- Surplice front creating a V neckline
- High waist seam
- Floral printed knit fabric
Model is 5'7" with a 32.5" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06001-2722
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All My Love Floral Mesh Bodysuit
Fall for this floral bodysuit as they all fall for you girl! This date-night in bodysuit brings the romance with its gorgeous floral print, plunging v-neckline, and sleek adjustable straps that offer a customized fit. Complete your date-night outfit with high waist jeans and duster earrings.
Fit & Features
- Plunging v-neckline
- Adjustable spaghetti straps
- Floral print
- Contrast bottom
- Snap button closure
- Sheer mesh fabric
- Form-hugging fit
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06001-2687
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ditsy Floral Ribbed Knit Tank
We love a good ditsy floral! This printed ribbed knit tank is perf for an everyday spring look.
Fit & Features
- Spaghetti straps
- Deep V neckline
- Multiple hook and eye front closures
- Cropped
- Ditsy floral print
- Ribbed knit fabric
- Plenty of stretch | Form hugging fit
Peach: Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Mint: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06001-2099
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ribbed Knit Scoop Neck Pajama Crop Top
Get ready to want to lounge all day, every day in this adorable ribbed knit pajama crop top! It features a comfy knit fabric and a form-hugging fit. Pair with some cute chunky sneakers for a movie marathon day.
Shop Matching Bottoms: Ribbed Knit Pajama Micro Shorts
Fit & Features
- Scoop neckline
- Tank-like shoulder straps
- Cropped hem
- Ribbed knit fabric
- Matching shorts sold separately
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07103-0363
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple And Sweet Pajama Crop Top
Cozy on up in this simple and sweet pajama crop top, a perf piece to add to your loungewear wardrobe! Featuring a soft knit fabric and form-hugging fit, this top is a must-have for a movie night. Pair with some cute slides to finish off the look.
Shop Matching Bottoms: Simple And Sweet Pajama Leggings
Fit & Features
- Short cap sleeves
- Crew neckline
- Cropped hem
- Knit fabric
- Matching leggings sold separately
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07103-0358
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ribbed Knit Pajama Micro Shorts
Get ready to want to lounge all day, every day in these adorable ribbed knit pajama micro shorts! They feature a comfy knit fabric and a form-hugging fit. Pair with some cute chunky sneakers for a movie marathon day.
Shop Matching Top: Ribbed Knit Scoop Neck Pajama Crop Top
Fit & Features
- High rise banded waist
- Short form-hugging fit
- Ribbed knit fabric
- Matching top sold separately
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07103-0364
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple And Sweet Pajama Leggings
Cozy on up in these simple and sweet pajama leggings, a perf piece to add to your loungewear wardrobe! Featuring a soft knit fabric and form-hugging fit, these leggings are a must-have for a movie night. Pair with some cute slides to finish off the look.
Shop Matching Top: Simple And Sweet Pajama Crop Top
Fit & Features
- High rise banded waist
- Tie front detail
- Tapered fit
- Knit fabric
- Matching top sold separately
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 07103-0359
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Babe High Slit Maxi Skirt
Channel vacay vibes in a tropical skirt that is perfect for days spent underneath a cabana. The high waist skirt features a tropical palm leaf print and a high side slit to show off a hint of leg. Complete your tropical-inspired look with the matching top and cork wedges.
Shop Matching Top: Tropical Babe Tie Front Crop Top
Fit & Features
- High rise waist
- Lightly pleated
- Tropical palm leaf print
- High side slit
- Lightweight woven fabric
- Matching top sold separately
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06301-0049
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rhinestone and Basic Band Multi Ring Pack
Stack on the glam with rings that slay! This multi-pack features a variety of rhinestone and flat metal rings that can be worn alone or stacked to create a unique look! Complete your look with a crop top and high waist jeans to nail that casual look down!
Fit & Features
- Pack includes 15 rings
- Rhinestones
- Flat metal design
- Available in gold and silver
Style Number/Barcode: 07004-0077
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rose Pendant Dainty Chain Necklace
Bring the charm with a necklace that shows off your sweet side. The dainty chain necklace is a must for dressing up your casual outfits. The necklace features a dainty chain, a rectangular pendant with a textured plate, and an engraved rose design. Complete your look with high waist jeans and a puff sleeve top.
Fit & Features
- Dainty chain
- Rectangular pendant, with a textured plate
- Engraved rose design
Style Number/Barcode: 07002-0516
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Beauty Chiffon Belted Kimono
Showcase effortless beauty in this gorgeous chiffon belted kimono. Featuring kimono style sleeves with ruffle detailing and a tie front belt, pair this over a chic satin pajama set for a relaxing day at home.
Fit & Features
- Kimono style sleeves with ruffle detailing
- Tie-front belted waist
- Flowy fit
- Sheer chiffon fabric
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 06204-0631
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Escape Tropical Print Tie-Front Top
Escape to your dream vacay in this tropical print tie-front top offering flowy short sleeves and a cropped, relaxed fit. Style with the matching palazzo pants and your fave sandals.
Shop Matching Bottoms: Sunny Escape Tropical Print Palazzo Pants
Fit & Features
- Woven fabric
- Tropical print
- Plunging V-neckline
- Flowy short sleeves
- Tie-front design
- Cropped hem, relaxed fit
- Runs true to size
Style Number/Barcode: 06204-000002
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sheer Support Tights
Keep it sleek and stylish in these sheer support tights! This pair of stockings will keep you firm and are supportive, while also looking classy and chic. Pair with a stunning mini dress for an overall gorgeous look.
Fit & Features
- High rise waist
- Firm and supportive
- Sheer look
Fashion tape, adhesive bras, adhesive panties, pasties, hosiery, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07306-0067
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brighter Vibes Lace-Up Chiffon Maxi Dress
Bring on brighter vibes in this maxi dress that brings a burst of color this season. The maxi dress features a plunging v-neckline, sexy waist cutout to show off a hint of skin, a lace-up back, and a high side slit. Complete your look with fab cork wedges and sunnies for those ultimate summer vibes.
Fit & Features
- Sleeveless v-neckline with spaghetti straps
- Waist cutouts
- Lace-up back
- High side slit
- Maxi length silhouette
- Chiffon fabric
Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0505
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classic Chic Scoop Neck Knit Mini Dress
Fall in love with the classic chic look of this adorable basic knit mini dress! It features bungee spaghetti straps and a short, flattering, curve-hugging fit. This dress can easily be dressed up with heels for date night or kept more casual with a bucket hat and chunky sneakers for a shopping day.
Fit & Features
- Bungee spaghetti straps
- Scoop neckline
- Mini-length silhouette
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-0897
Category Name: Vacation Looks
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Skirt Skirt Skater Dress
This dress will be the center of all the tea at your next afternoon soiree.
Fits & Features
- Deep Sweetheart Neckline I Princess Seams
- Dual Spaghetti Straps That Cross At The Back
- High Waist Seam
- Flattering Skater Skirt
- Thick Knit Composition
- Plenty Of Stretch
Style Number/Barcode: 05101-7961
Category Name: Vacation Looks
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Eyelet Mini Skirt
Create an effortless everyday look in this eyelet mini skirt that is a must have for your summer vibe. Perfect paired with the matching crop top for a chic photoshoot in your backyard! The adorable skirt features a flattering high waist and a curve hugging fit. Complete your cute outfit with some classic gold hoops and trendy wedges.
Shop Matching Top: Effortless Eyelet Puff Sleeve Crop Top
Fit & Features
- High rise waist
- Short, form hugging fit
- All over eyelet detail
- Lined
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06501-0271
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Babe Tie Front Gauze Crop Top
Channel vacay vibes in a tropical top that is perfect for days spent underneath a cabana. The top features a tropical palm leaf print, a tie front accent at the center of the bodice, and a cropped hem. Complete your look with the matching skirt and sleek hoop earrings.
Shop Matching Skirt: Tropical Babe High Slit Maxi Skirt
Fit & Features
- Sleeveless sweetheart neckline
- Tie front accent
- Tropical palm leaf print
- Adjustable spaghetti straps
- Cropped hem
- Smocked back
- Composed of a gauze knit fabric
Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06003-0619
Category Name: Vacation Looks
Price: $4.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Kailey High Rise Bermuda Shorts
Oasis by Eunina
Channel chic vibes in shorts that are anything but basic! The shorts feature a high rise waist, a single button with zipper closure, a traditional five-pocket with belt loop design, and a Bermuda length. Complete look with a sleek bodysuit and strappy sandals.
Fit & Features
- High rise waist
- Single-button with zipper closure
- Traditional five-pocket with belt loop design
- Bermuda length with fringed hem
- Light-medium acid wash
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06603-0144
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Diva Sleeveless Tie Waist Jumpsuit
Dare to impress in a denim jumpsuit that stuns for your next date night! The jumpsuit features a sleeveless plunging scoop neckline, a zippered front, a tie waist belt with belt loops and a straight leg fit with a flared hem. Complete your look with fringe earrings and wedge heels.
Fit & Features
- Sleeveless scoop neckline
- Tank-like shoulder straps
- Zippered front
- Tie-waist belt with belt loop
- Slant pockets
- Straight-leg fit with a flared hem
- Form hugging denim fabric, moderate stretch
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06602-0196
Category Name: Vacation Looks
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flirty Floral Polka Dot Mini Dress
Create a flirty first impression in this pretty floral polka dot mini dress! It features a cowl neckline, a flowy mini length silhouette, and a fun floral print on a polka dot woven fabric. For a cute day date look, layer on a denim jacket and pair with some clear heels.
Fit & Features
- Adjustable spaghetti straps
- Cowl neckline
- Flowy mini length fit
- Floral print
- Polka dot woven fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0914
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fall For Floral Woven Midi Dress
Fall head over heels for this adorable ditsy floral midi dress! Featuring a trendy cowl neckline and a flowy mid-length silhouette, this dress would pair perfectly with some simple gold hoops and clear mules. Wear to your next brunch with your girls and you'll receive all the compliments.
Fit & Features
- Adjustable spaghetti straps
- Cowl neckline
- Flowy mid-length fit
- Ditsy floral print
- Woven fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0882
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simple And Sleek Tie Shoulder Slip Dress
Simple and sleek, this slip dress is a gorgeous piece you need to have in your closet. Featuring tie shoulder straps and a flowy mid-length silhouette, it can so easily be dressed up with some clear mules or down with chunky sneaks. Wear to your next date with bae and you'll leave a lasting impression.
Fit & Features
- Tie shoulder straps
- Slight V neckline
- Square back
- Flowy mid-length fit
- Woven fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0895
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance