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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Always A Vibe Basic Knit Tank Top
This basic tank top is always a vibe! With a sleek square neckline and form-hugging fit, this top is essential for creating cute fits'.
Fit & Features
- Stretchy knit fabric
- Square neckline
- Wide shoulder straps
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06002-000027
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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50s Icon Halter Plunge Neck Skater Romper
Chanel a popular 50s iconic look in this halter plunge skater romper perfect for themed parties or summer holidays! With a flattering halter neckline and charming tie closure, this romper will create a stunning silhouette. The skater shape and short hem add to its playful appeal. Complete the look with hoop earrings.
Fit & Features
- Smooth cotton-blend knit fabric, moderate stretch
- Halter plunge neckline, tie closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 06503-1138
Category Name: Vacation Looks
Price: $18.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK, BROWN
Available Size: S, M
Product Badge:- Sale
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All Time Favorite Strappy Metallic Flat Sandals
Discover your new favorite pair of metallic sandals! They feature a chic square toe and a strappy design that will elevate any outfit. And with their flat sole and metallic faux leather material, they provide a chic and comfortable style. Complete the look with a tote purse.
Fit & Features
- Square toe
- Flat sole
- Strappy design
- Metallic faux leather material
- Runs true to size
Style Number/Barcode: 07404-1084
Category Name: Vacation Looks
Price: $8.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish In The Chill Puffer Jacket
Keep stylish through the chill in this quilted puffer jacket featuring long sleeves with buttoned cuffs, a collar neckline, snap-button down front closures, flap pockets, and a cropped hem. The jacket is designed with thin insulation to help keep you comfortable and protected from the elements. Style over a long sleeve top with woven joggers.
Fit & Features
- Long sleeves, buttoned cuffs, collar neckline
- Snap-button down front closures
- Flap pockets
- Cropped hem
- Quilted thin puffer woven fabric
- Insulated and lined
- Fits true to size
Style Number/Barcode: 06201-0317
Category Name: Vacation Looks
Price: $17.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Distressed High Waist Cut-Off Denim Shorts
These trendy distressed high waist cut-off denim shorts are a summer closet staple! Made with a stretchy cotton-blend denim fabric, they feature a flattering high-rise waist, a fitted silhouette, distressed detailing, and a frayed cut-off hem for an edgy vibe. Include a five-pocket and belt loop design with a front button and hidden zipper closure. Style these jean shorts with a crop top and sneakers.
Fit & Features
- Cotton-blend denim fabric, moderate stretch
- High waist
- Fitted
- Distressing, frayed cut-off hem
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Runs true to size
Style Number/Barcode: 06603-0377
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Serve Looks Square Sunglasses
Serve nothing but cute looks in these square sunglasses for UV protection and stylish flair!
Fit & Features
- Square frames
- Tinted colored lenses
- 100% UV protection
Style Number/Barcode: 07008-000015
Category Name: Vacation Looks
Price: $4.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Babe Strapless Lace-Up Striped Crop Top
Level up your summer 'fits like the bold babe you are with this strapless lace-up crop top! Made with a striped ribbed knit fabric, it offers plenty of stretch. The tube top features a strapless straight-across neckline, a trendy lace-up front with an alluring cutout design and tie closure, and a cropped hem with a form-hugging fit for that snatched look. Style with wide-leg pants for a chic vibe.
Fit & Features
- Stretchy striped ribbed knit fabric
- Strapless straight neckline
- Lace-up front with tie closure
- Cropped
- Fitted
- Runs true to size
Style Number/Barcode: 06002-1867
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beauty On Vacay Cutout Abstract Maxi Dress
From seaside dinners to dancing under the moonlight, this abstract print maxi dress will have you looking like a beauty on the island! It features delicate spaghetti straps, a sweetheart neckline with an O-ring bust insert, a cutout bodice to reveal some skin, and a flattering bodycon silhouette and maxi-length hem. Complete the look with strappy wedges.
Fit & Features
- Abstract print, knit fabric, short knit lining
- Spaghetti straps
- Sweetheart neckline
- O-ring bust insert, cutout
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5584
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Light High Rise Linen Palazzo Pants
Keep it light and effortless in these high-rise linen palazzo pants for a day spent under the sun! With a high-rise waist and side pockets, these pants offer both a flattering fit and convenience. The palazzo wide-leg silhouette keeps you comfortable, while the linen fabric elevates the look. Style with the matching top.
Shop Matching Top: Keep It Light Sleeveless Linen Corset Top
Fit & Features
- Linen woven fabric, no stretch
- High-rise waist, stretchy smocked back waistband
- Pockets
- Palazzo wide-leg silhouette
- Runs true to size
Style Number/Barcode: 06302-0815
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Never Blend In Butterfly Chain Necklace
Never blend in but stand out in this butterfly chain necklace secured with a lobster clasp closure. Complete the look in high heels for a dressy occasion.
Fit & Features
- Butterfly charms
- Chain link
- Lobster clasp closure
Style Number/Barcode: 07002-1864
Category Name: Vacation Looks
Price: $3.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Staple Ribbed Knit Bandeau Top
This casual ribbed knit bandeau top is a staple style to have in your closet. Pair with your fave high-rise bottoms or layered under cute tops!
Fit & Features
- Stretchy ribbed knit fabric
- Strapless straight neckline
- Cropped hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 07109-000001
Category Name: Vacation Looks
Price: $6.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Next Chapter High-Rise Carpenter Denim Shorts
Write your next stylish chapter in these high-rise denim shorts! With a high-rise waist and form-hugging fit, these shorts accentuate your curves while providing comfort. Plus, the bottom side strap and mini pocket add a unique touch to the medium-wash denim fabric. Complete the look in a graphic tee for casual plans!
Fit & Features
- Medium wash denim, slight stretch
- High rise waist
- Form-hugging fit
- Bottom side strap and mini pocket accent
- Front button and hidden zipper closure
- Five-pocket styling
- Runs true to size
Style Number/Barcode: 06603-0368
Category Name: Vacation Looks
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Breezy Energy Tie Front Long Sleeve Linen Top
This linen crop top boasts breezy energy for effortless summer styling! Featuring stylish bell sleeves and a trendy tie-front design, this top will elevate your fashion game. The cropped hem adds a modern touch. Complete the look in a denim mini skirt and sandals.
Fit & Features
- Linen blend fabric, no stretch
- Bell long sleeves
- Tie-front design
- Cropped length
- Runs true to size
Style Number/Barcode: 06204-1760
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Watch Me Bloom Off-The-Shoulder Floral Midi Dress
Be the talk of any garden party in this floral midi dress! The off-the-shoulder neckline exudes femininity, while the cutout waist shows some skin. The flowy midi-length silhouette and front slit offer a trendy allure. Complete the look in lace-up heels and earrings.
Fit & Features
- Floral print, woven fabric with lining, no stretch
- Off-the-shoulder neckline
- Cutout waist
- Front slit
- Flowy midi-length silhouette
- Runs true to size
Style Number/Barcode: 05101-3414
Category Name: Vacation Looks
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hot Cowgirl Summer Trucker Hat
Embody the country vibes in this trucker hat all season! It features a classic curved wide brim, an embroidered script that reads "Hot Cowgirl Summer" and a mesh back with adjustable snap-back closures. Complete the look in a denim jumpsuit.
Fit & Features
- Curved wide brim
- Embroidered script reads "Hot Cowgirl Summer"
- Mesh back with adjustable snap-back closures
Style Number/Barcode: 07302-1649
Category Name: Vacation Looks
Price: $4.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fit To Bloom Scoop Neck Ditsy Floral Midi Dress
Sweet summer events are calling and this ditsy floral midi dress is here to make you look cute! Adjustable spaghetti straps and a drawstring scoop neckline provide versatile style, while the form-hugging fit and side slit add a touch of sass. Complete the look in high heels.
Fit & Features
- Ditsy floral print, bust lining, knit fabric, moderate stretch
- Spaghetti straps
- Drawstring adjustable scoop neckline, bust tie
- Form-hugging fit
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5774
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daily Cute Vibe Twist V-Neck Crop Top
Always cute every day, this seamless crop top is perfect for creating alluring looks! Made with seamless rib knit fabric, this crop top is not only stylish but also comfortable. The spaghetti straps and V-neckline provide a sleek and sexy silhouette, while the twist bust adds a touch of flirtiness to the cropped hem that shows off your curves. Complete the look in best-selling bottoms and heels.
Fit & Features
- Seamless rib knit fabric, double-lined, moderate stretch
- Spaghetti straps
- V-neckline
- Twist bust
- Cropped length
- Runs true to size
Style Number/Barcode: 07109-0402
Category Name: Vacation Looks
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Trending Strapless Striped Bodycon Mini Dress
Trend right in this strapless mini dress featuring a twist sweetheart neckline with a keyhole cutout and a flattering bodycon silhouette. The striped knit material hugs your curves making it perfect for pairing with sneakers or sandals.
Fit & Features
- Striped print, stretchy knit material
- Strapless sweetheart twist neckline
- Keyhole cutout
- Bodycon mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5824
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Short But Sweet Gingham Bow Shorts
Short but super sweet! These gingham shorts are the cherry on top of a perfect sunny day look featuring a flattering high-rise waist and side bow ties.
Fit & Features
- Gingham print, cotton woven fabric
- High-rise elasticized waist
- Hidden side pockets
- Side bow ties
- Fitted hem
- Runs true to size
Style Number/Barcode: 06303-000017
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty Luxe Rhinestone Charm Belly Chain
This dainty rhinestone charm belly chain is dotted with shimmering charms—perfect for layering or letting it shine solo on your next night out.
Fit & Features
- Rhinestone charms
- Dainty chain
- Lobster clasp closure
Style Number/Barcode: 07002-000190
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Ready Tropical Knit Halter Crop Top
This alluring tropical halter crop top will have you ready for a dreamy vacay! The lined stretchy knit fabric features a bold abstract tropical print pattern to catch all the glances on your getaway. The crop top is shaped with a sleeveless halter neckline with a sultry V-shaped cutout, tie-back halter straps, ruched side seams to accentuate your curves, and a form-hugging fit for a snatched look. Style with the matching wide-leg pants and hoop earrings.
Shop Matching Bottoms: Vacay Ready Tropical Knit Wide-Leg Pants
Fit & Features
- Abstract tropical print
- Stretchy lined knit
- Halter neckline, V-shaped cutout
- Tie-back spaghetti straps
- Ruched side seams
- Fitted cropped hem
- Runs true to size
Style Number/Barcode: 06001-5210
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beachy-Chic Shell Thong Strap Sandals
These beachy-chic shell thong strap sandals are a style staple for your summer vacay! Made with faux leather, they feature an almond toe, a trendy thong strap design with sleek oval-shaped shell accents, thin adjustable ankle and heel straps with a buckle closure, and a flat sole for comfortable wear. Pair with a crochet top and denim shorts!
Fit & Features
- Faux leather upper
- Almond toe
- Thong strap design
- Oval shell accents
- Adjustable ankle and heel straps with buckle closure
- Flat sole
- Runs true to size
Style Number/Barcode: 07404-1208
Category Name: Vacation Looks
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knit The Beach Striped Strappy Crochet Crop Top
This striped crochet crop top is all about the beach life! Featuring a square neckline, spaghetti straps, and a strappy open back, this top is perfect for summer fun. Its cropped hem adds a trendy touch. Complete the look in denim shorts.
Fit & Features
- Striped pattern, crochet fabric, no stretch
- Square neckline
- Spagehtti strap, strappy open back
- Cropped hem
- Runs true to size
Style Number/Barcode: 06005-2007
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Girl Next Door Vibes Cropped Tank
Look like the total girl next door in this basic cropped tank. This staple piece goes with everything from your casual looks or as a layering piece for a dressed-up look. The cropped tank features a sleeveless bodice and bungee spaghetti straps for a secure and comfortable fit. Complete your girl-next-door look with high waist jeans and a pair of sneakers.
Shop In More Colors: Girl Next Door Cropped Tank
Fit & Features
- V-neckline
- Bungee straps
- Cropped
- Knit fabric
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06001-4459
Category Name: Vacation Looks
Price: $6.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free