Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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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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Vineyard Gal Floral Woven Skater Dress
This vintage-inspired floral woven dress is perfect for vineyard weddings, wine tastings, and daytime soirees! The skater dress features adorable short puff sleeves, a sweetheart neckline with a bust tie, a lace-up back design, and a tiered fit-and-flare skater silhouette with a short hem. The lined woven fabric showcases a vintage floral print pattern. Style this short dress with on-trend strappy mules.
Fit & Features
- Short puff sleeves
- Sweetheart neckline, bust tie
- Lace-up back design, tie closure
- Tiered fit-and-flare skater silhouette
- Short-length hem
- Vintage floral print, lined woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05101-2966
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Leaving An Impression Striped Ribbed Knit Midi Dress
Leave an impression in this striped knit midi dress everywhere you go! With adjustable spaghetti straps, a sweetheart neckline, a cutout bust, and a form-hugging fit, this dress is both stylish and comfortable. The dual side slits add a trendy flair to the midi-length hem. The ribbed knit fabric offers plenty of stretch. Complete the look in sandals and sunglasses!
Fit & Features
- Striped pattern, stretchy ribbed knit fabric
- Adjustable spaghetti straps
- Sweetheart neckline
- Cutout bust
- Form-hugging fit
- Dual side slits
- Runs true to size
Style Number/Barcode: 06005-1976
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pop Of Cute Straw Faux Leather Flat Sandals
Add a pop of cute to your outfit in these faux leather flat sandals for everyday styling! These sandals are the perfect combination of comfort and style, featuring a sleek square toe and a trendy straw band with notch cutouts on faux leather material. Complete the look with a chic pair of sunglasses.
Fit & Features
- Square toe
- Straw band with notch cutouts
- Flat sole
- Faux leather material
- Runs true to size
Style Number/Barcode: 07404-1231
Category Name: Vacation Looks
Price: $12.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Spot Strapless Floral Chiffon Romper
The perfect romantic floral chiffon romper for summer date nights or soirees! Made from delicate ditsy floral and polka dot printed chiffon fabric, this romper exudes a playful and feminine charm. The strapless neckline and tie-back design offer a perfect fit while the flowy short-length hem adds a touch of elegance. Complete the look with high heels.
Fit & Features
- Ditsy floral and polka dot print
- Chiffon fabric lined with woven fabric
- Strapless neckline
- Back zipper and hook-eye closure
- Flowy short-length
- Runs true to size
Style Number/Barcode: 06403-0546
Category Name: Vacation Looks
Price: $20.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Admired Scoop Neck A-Line Mini Dress
You'll always admire having this sleeveless mini dress for dressing up or down! Made from lined stretchy rib knit fabric, this dress hugs your curves in a flattering A-line silhouette. The scoop neckline and thin spaghetti straps add a flattering look. Style with a cute jacket and your favorite sneakers!
Fit & Features
- Stretchy rib knit fabric, full knit lining
- Spaghetti straps
- Curve-hugging, A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5652
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeter Than Floral Short Sleeve Tie-Back Romper
What could be sweeter than you in this floral romper? Play up your style in this must-have romper for the spring-to-summer season. The ruffle trim puff sleeves add a whimsical touch, while the form-hugging silhouette and tie-back detail create a flattering fit. With a short-length hem and a square neckline, this romper is flattering for any occasion! Complete the look in heeled sandals and hoop earrings.
Fit & Features
- Floral print, woven fabric with full woven lining
- Tie-back design
- Back zipper and hook-eye closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06403-0441
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Main Frame Oversized Square Sunglasses
These oversized sunglasses will be your main pick for a casual-cute style all season long! They feature an oversized plastic square frame with gold trim, built-in nose pads, tinted lenses, and a comfortable fit. Complete the look with sleek jewelry.
Fit & Features
- Oversized plastic square frames
- Gold trim
- Built-in nose pads
- Tinted lenses
- Comfortable fit
- 100% UV protection
Style Number/Barcode: 07008-1075
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Classic Trendsetter Rectangle Sunglasses
A classic trendsetter like yourself needs a pair of iconic rectangle sunglasses as an everyday staple. These sunnies feature a small rectangular-shaped design with a plastic frame and arms, built-in nose pads, and tinted lenses. Style with a chic shoulder bag.
Fit & Features
- Small rectangular-shaped design
- Plastic frame and arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1098
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Looking Sleek Square-Frame Sunglasses
Accessorize your fave 'fits with these square-frame sunglasses for a sleek and chic vibe. The sunnies feature a classic square-shaped design with a plastic frame and arms, built-in nose pads, and tinted lenses. Style with hoop earrings.
Fit & Features
- Square-shaped design
- Plastic frame and arms
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1076
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tuscan Charm Strapless Slit Eyelet Maxi Dress
You'll be so charming in Tuscan wearing this eyelet maxi dress as the stunning new bride or chic traveler! The eyelet fabric adds a touch of delicacy, making it the perfect dress for any occasion. With a form-hugging fit and a high-side slit, this dress exudes confidence and elegance! Complete the look with earrings.
Fit & Features
- Eyelet fabric, sewn-knit lining, minimal stretch
- Strapless neckline
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5637
Category Name: Vacation Looks
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Nautical Vibes Striped Ribbed Knit Cropped Tank Top
Show off trendy nautical vibes this season in this casual striped knit tank top! Made with an ultra-stretchy ribbed knit fabric, the crop top features a sleeveless notched V-neckline, thin tank shoulder straps, and a form-hugging fit for a snatched look. Style with high-rise jean shorts and sneakers for your laid-back weekend plans.
Fit & Features
- Stretchy ribbed knit fabric
- Notched V-neckline
- Tank straps
- Cropped
- Fitted
- Runs true to size
Style Number/Barcode: 07109-0383
Category Name: Vacation Looks
Price: $9.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Vibes Boho Print Knit Flare Pants
Channel those effortless and breezy vibes in these boho print knit flare pants perf for festival season. The soft and stretchy brushed knit fabric features a trendy bohemian-inspired multi-print pattern for an eye-catching look. The high waist has a V-front design to create that snatched silhouette, with a back elastic band for comfortable wear. The hip-hugging fit continues through the leg, leading to a flared hem. Complete your outfit with a crochet top and strappy sandals!
Fit & Features
- Stretchy brushed knit fabric
- Bohemian multi-print pattern
- High waist with V-front design
- Back elastic band
- Hip-hugging fit
- Flared leg
- Runs true to size
Style Number/Barcode: 06502-2440
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Season Ruffled Wrap-Front Woven Romper
Create a chic vibe for your summer plans in this ruffled wrap-front romper! Designed with a lightweight woven fabric, it features a surplice V-neckline with a flirty ruffled trim, adjustable spaghetti straps for a customized fit, and a secure back zipper closure. The high waist is accented with a chic wrap-front overlay with a tie-front design and an envelope hem, layered over fitted shorts. Complete the look with strappy sandals for a weekend getaway.
Fit & Features
- Woven fabric with no stretch, lining
- Surplice V-neckline with ruffled trim, hook and eye closure
- Adjustable spaghetti straps
- Hidden back zipper with hook and eye closure
- Wrap-front overlay, tie-front, envelope hem
- Fitted shorts
- Runs true to size
Style Number/Barcode: 06403-0542
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feeling Good Criss Cross Faux Leather Flat Sandals
Slip on these flat sandals you'll be feeling good and looking stylish! The round-toe design and micro suede footbed offer all-day comfort, while the crisscross faux leather straps add a touch of chic to any look. Complete the look with a crossbody bag.
Fit & Features
- Round toe
- Crisscross faux leather straps
- Flat sole
- Micro suede footbed
- Runs true to size
Style Number/Barcode: 07404-1178
Category Name: Vacation Looks
Price: $12.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Stylish Linen Dress
You'll look effortlessly stylish this season in this lightweight and flowy linen dress! Designed with a breezy woven fabric, this short dress is perfect for your summer parties. The bodice is shaped with a square neckline with ruching at the bust and long balloon sleeves. The fitted waistband creates a cinched silhouette, flowing out to a short ruffled hem with an A-line fit for a pretty flair. Complete the look with clear heels.
Fit & Features
- Linen woven fabric, no stretch
- Square neckline, ruched bust
- Long balloon sleeves, elastic cinched hems
- Front waistband, back zipper closure
- Ruffled hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-4246
Category Name: Vacation Looks
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Instant Classic Aviator Sunglasses
These sleek aviator sunglasses will be an instant classic and staple for the season! They feature a traditional aviator design with tinted lenses, a thin metal frame with thin arms, a brow bar and nose bridge, and rubber nose pads for support. Style these sunnies with a denim jacket for that casual-cool vibe.
Fit & Features
- Aviator design
- Tinted lenses
- Thin metal frame and arms
- Thin brow bar and nose bridge
- Rubber nose pads
Style Number/Barcode: 07008-1046
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Icon Oversized Cat-Eye Sunglasses
Elevate your trendy looks with these sleek cat-eye sunnies! The sunglasses feature an oversized cat-eye design, a thin metal frame and nose bridge, plastic arms, rubber nose pads, and tinted lenses. Style with strappy sandals.
Fit & Features
- Oversized cat-eye design
- Thin metal frame and nose bridge
- Plastic arms
- Rubber nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1069
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Flair Oversized Square Sunglasses
These chic oversized sunnies will add that bold flair to your fave looks! The sunglasses feature an oversized square-shaped design, a thin metal frame and nose bridge, sleek side accents, thin metal arms, rubber nose pads, and tinted lenses. Style with chunky hoop earrings.
Fit & Features
- Oversized square-shaped design
- Thin metal frame and nose bridge
- Side accents
- Thin metal arms
- Rubber nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1068
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ready Set Chic Oversized Square Sunglasses
Amp up the chic vibes of your looks with these oversized shades! The sunglasses feature an oversized square-shaped design, a thin metal frame, sleek chain-link designed arms, rubber nose pads, and tinted lenses. Style with hoop earrings.
Fit & Features
- Oversized square-shaped design
- Thin metal frame and nose bridge
- Chain-link designed arms
- Rubber nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1064
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Drama Oversized Square Sunglasses
These fabulous oversized square sunglasses will bring the chic drama and level up your looks! They feature an oversized angled square-shaped design, a plastic frame and arms with sleek metal accents at each side, built-in nose pads, and tinted lenses. Style with a chain necklace.
Fit & Features
- Oversized angled design
- Plastic frame and arms
- Metal accents
- Built-in nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1063
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So 2000s Square-Shaped Sunglasses
Bring that early 2000s energy to your everyday looks with these trendy sunnies! The sunglasses feature a Y2K-inspired square-shaped design, a thin metal nose bridge, thin metal arms with a sleek cutout design, rubber nose pads, and tinted lenses. Style with a mini handbag.
Fit & Features
- Square-shaped design
- Metal nose bridge
- Cutout metal arms
- Rubber nose pads
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-1062
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Clear Intentions Crossbody Bag With Straw Pouch
Keep your style in the clear with this crossbody bag with a convenient straw pouch! Perfect for any occasion, this bag features a chain crossbody shoulder strap, a top flap with turn lock closure, and a straw zipper pouch for keeping extra essentials in. Complete the look with sandals.
Fit & Features
- Clear crossbody bag
- Chain crossbody shoulder strap
- Front flap with turn-lock closure
- Straw zipper pouch
Style Number/Barcode: 07203-1978
Category Name: Vacation Looks
Price: $12.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Contemporary Cutie Clear Cork High Heel Sandals
Contemporary and cute, these high heel sandals are a fresh find for all of your upcoming spring-to-summer occasions! Features a comfortable almond toe and a clear PVC band, adding a touch of modern style. The block heel provides stability and a subtle boost, a lightly cushioned insole ensures all-day comfort, while the cork material offers a chic finish. Complete the look with a trendy crossbody bag.
Fit & Features
- 4" Block heel
- Almond toe
- Clear PVC band
- Lightly cushioned insole
- Cork material
- Runs true to size
Style Number/Barcode: 07401-4831
Category Name: Vacation Looks
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Factor Oversized Square-Shaped Sunglasses
Amp up the sleek factor of your 'fits with these fab oversized shades! The sunglasses feature a trendy oversized square-shaped design with a thin metal frame, thin metal arms, sleek cutout accents at each side, and tinted lenses. Style with hoop earrings and a chain necklace.
Fit & Features
- Oversized square-shaped design
- Thin metal frame, thin metal arms
- Rubber nose pads
- Cutout sides
- Tinted lenses
Style Number/Barcode: 07008-1067
Category Name: Vacation Looks
Price: $4.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free