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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Major It-Girl Satin Midi Skirt
Bring the it-girl energy to your everyday look with this on-trend midi skirt. It features a high-rise waist, a V-wired front accent with ruched detailing, straps to lace up around the waist, a midi-length hem, a curve-hugging silhouette, and a high side slit. Style with a crop top and mules.
Fit & Features
- High-rise waist, V-wired front accent, ruching
- Thin straps to lace up around the waist
- Midi-length hem, fitted bodycon silhouette
- High side slit
- Smooth satin-knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06401-0492
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Minimalistic Sultry Midi Dress
Chanel a sultry minimalistic wardrobe for fall in this staple crepe midi dress featuring a sleek sleeveless V-neckline, bungee spaghetti straps, a curve-hugging silhouette, and a front slit accent. Complete the look in low-heeled mules and a chic hat.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Curve-hugging silhouette
- Front slit accent
- Midi-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4782
Category Name: Vacation Looks
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Your Favorite Crop Denim Shacket
Effortlessly laid back and cool, your favorite crop denim shacket to layer over your cutest daily fits! It features long sleeves with button cuffs and trendy distressed accents, a collar neckline, snap button-down closures, flap pockets, and a relaxed, curved hemline. Complete the look in a cute casual dress.
Fit & Features
- Collar neckline
- Long sleeves, button cuffs, distressed accents
- Snap button-down closures
- Flap pockets
- Relaxed fit, curve crop hemline
- Light wash non-stretch denim
- Runs true to size
Style Number/Barcode: 06203-0475
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Collar neckline
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Perfect Trio Three Pack Anklets
The perfect trio of anklets to adorn your semi-formal wear! This three-pack set features one snake chain anklet, one rhinestone charm anklet, and a multi-chain link anklet each with a lobster clasp closure. Complete the look in stiletto heels.
Fit & Features
- Three-pack anklet set
- One snake chain anklet
- One rhinestone charm anklet
- One multi-chain link anklet
- Each has a lobster clasp closure
Style Number/Barcode: 07003-0326
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Sided Cutout Back Bodysuit
Charm the crowd in this one-shoulder bodysuit featuring a long sleeve, form-fitting bodice, and a sultry cutout back. Complete the look in boyfriend jeans for dinner with friends.
Fit & Features
- One-shoulder neckline
- Long sleeve
- Form-fitting bodice
- Cutout back design
- Thong bottom, snap button closures
- Stretchy knit fabric
- Fits true to size
Style Number/Barcode: 06001-4410
Category Name: Vacation Looks
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Bow Charm Cat Eye Sunglasses
The dainty bow detail on these sunglasses adds a soft-girl twist to this fierce cat eye shape—perfect for brunch 'fits, content days, or any moment you wanna look cute and unbothered.
Fit & Features
- Sleek cat eye frames
- Bow charm
- TInted lenses
- 100% UV protection
Style Number/Barcode: 07008-000057
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Downtown Nights Wide-Leg Pants
Stroll downtown tonight in these breezy wide-leg pants featuring a high-rise waist, hidden side pockets, and pleats going down the front on woven fabric with minimal stretch. Complete the look in a one-shoulder top and mules.
Fit & Features
- High-rise waist
- Hidden side pockets
- Pleats down the front
- Wide-leg silhouette
- Pull-on/off styling
- Woven fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 06402-0526
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Elevated Basic Sweater Knit Bodysuit
Step up your look with this elevated basic bodysuit! Featuring a sleeveless crew neckline, an asymmetrical cutout above the bust, and a form-hugging fit, you can effortlessly transition this bodysuit from day to night. Style with high-rise denim and heeled booties for every day, and faux leather pants and mules for nights out.
Fit & Features
- Sleeveless crew neckline
- Asymmetrical cutout above the bust
- Thong bottom, dual snap-button closure
- Ribbed sweater knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1550
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Babe In Pointed Toe Boots
Walk tall babe in these PU pointed-toe boots featuring a stylish and sleek under-the-knee silhouette with a block heel and side zipper closure. Complete the look with a boyfriend blazer.
Fit & Features
- Pointed toe
- Block heel
- Side zipper closure
- Under-the-knee length
- PU material
- Runs true to size
Style Number/Barcode: 07402-0796
Category Name: Vacation Looks
Price: $12.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knit Alone Mock Neck Top
Cute alone but better together! This rib-knit top features a sleeveless mock neckline and a cropped hem. Complete the look in the matching bottoms and clear strap heels.
Shop Matching Bottoms: Knit Alone Slit Maxi Skirt
Fit & Features
- Mock neckline
- Sleeveless
- Cropped hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06001-4439
Category Name: Vacation Looks
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Knit Alone Slit Maxi Skirt
Cute alone but better together! This rib-knit maxi skirt features a high-rise waist, a curve-hugging silhouette, and an asymmetrical slit hem. Complete the look in the matching top and clear strap heels.
Shop Matching Top: Knit Alone Mock Neck Top
Fit & Features
- High-rise elasticized waist
- Curve-hugging silhouette
- Asymmetrical slit
- Maxi-length hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06501-0685
Category Name: Vacation Looks
Price: $6.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fell For You Knit Twist Bra Top
They'll fall for you in this knit bra top featuring a sleeveless V-neck, tank-style straps, a twisted bodice, and a cropped hem on sweater ribbed-knit fabric with minimal stretch. Complete the look in the matching cardigan.
Shop Matching Cardigan: Fell For You Knit Open Cardigan
Fit & Features
- Sleeveless, V-neck
- Tank-style straps
- Twisted bodice
- Cropped hem
- Sweater ribbed-knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1409
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Angel Number Necklaces
Support, alignment, and protection. Let this angel number necklace be a positive reminder of aspects of everyday life. It features a dainty chain link with coin accents and numerical charms. Complete the look in a casual dress and your fave sneakers.
Fit & Features
- Dainty chain link
- Coin accents
- Numerical charms with meanings
- 222 alignment, 333 support, 444 protection
- Lobster clasp closure
Style Number/Barcode: 07002-1336
Category Name: Vacation Looks
Price: $3.97 $8.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All The Class Crepe Wide Leg Pants
These crepe trouser pants have all the class your outfit needs for office hours to happy hour! They feature a high-rise waist with faux button accents, a wide-leg silhouette, and a pull-on/off styling. Complete the look in a blazer and heels.
Fit & Features
- High-rise waist
- Faux button accents
- Wide-leg silhouette
- Crepe knit fabric, moderate stretch
- Pull-on/off styling
- Fits true to size
Style Number/Barcode: 06502-1277
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Walking Knit Style Block Booties
Take stylish steps in these block heel booties featuring an on-trend pointed toe, partial knit and faux leather material, and an above-the-ankle length. Complete the look in a chic blazer.
Fit & Features
- Pointed toe
- Block heel
- Above-the-ankle length
- Partial knit and faux leather material
- Pull-on/off styling
- Runs true to size
Style Number/Barcode: 07403-1611
Category Name: Vacation Looks
Price: $12.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cadet Girl Cargo Mini Skirt
Command the room as the fashion cadet ready for duty in this cargo mini skirt featuring a high-rise waist, front button closure, belt loop accents, side flap pockets, and a bodycon silhouette. Complete the look in a cool graphic tee and boots.
Fit & Features
- High-rise waist
- Front button and hidden zipper closure
- Belt loop accents, side flap pockets
- Bodycon silhouette
- Mini-length hem
- Woven cotton fabric, slight stretch
- Runs true to size
Style Number/Barcode: 06301-0151
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Sleek Zebra Print Midi Dress
Keep your look so sleek with a midi dress that levels up your casual outfits! It features a sleeveless V-neckline with a knot-front design, a small keyhole cutout under the bust, spaghetti straps, a midi-length, fitted, A-line sihouette, and a chic front slit. The smooth knit fabric features an all-over zebra print pattern. Stye with strappy mules.
Fit & Features
- Sleeveless V-neckline, knot-front design
- Keyhole cutout under the bust
- Spaghetti straps
- Midi-length hem, fitted A-line silhouette
- High front slit
- Knit fabric, plenty of stretch
- Zebra print
- Runs true to size
Style Number/Barcode: 05102-4703
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Refresh Striped Sweater Dress
Refresh your closet in this striped sweater dress featuring a sleeveless, crew neckline, bodycon silhouette, and a mini-length hem on stretchy, rib-knit fabric. Complete your trendy look in statement heels.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless, crew neckline
- Bodycon silhouette
- Mini-length hem
- Striped pattern
- Stretchy rib-knit fabric
- Fits true to size
Style Number/Barcode: 06005-1485
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Snake Chain And Stud Earrings Set
Style up your casual looks with this sleek necklace and dainty earrings set! It features a flat snake chain necklace with a V-shaped design and small round stud earrings. Pair this jewelry set with a statement ring to complete your trendy glam look.
Fit & Features
- Necklace and earrings set
- Flat snake chain necklace, V-shaped design
- Adjustable chain, lobster clasp closure
- Small round stud earrings
- Post-back closures
Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.
Style Number/Barcode: 07002-1329
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Barefoot Bliss Strapless Crochet Maxi
Sun, sand, and this dress—name a better trio. The strapless twist neckline and open-knit crochet bring breezy beach goddess vibes with zero effort required. Perfect for sunset cocktails on vacay or a beach date!
Fit & Features
- Crochet fabric, knit lining
- Strapless twist neckline
- Curve-hugging fit
- Center back slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000011
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Silhouette Midi Sweater Dress
This curve-hugging sweater dress was made for sunset happy hour! It features a sleeveless V-neckline with a twist-front design, a center cutout under the bust, tank shoulder straps, and a midi-length, form-fitting silhouette with a chic high side slit. Style with classic hoop earrings and clear mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Sleeveless V-neckline, twist-front accent
- Center cutout under the bust
- Tank shoulder straps
- Midi-length hem, form-fitting silhouette, high side slit
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1462
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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LA Rider Graphic Seam Short Dress
Born to ride? Cruise through the streets of LA in this graphic short dress featuring cap sleeves, a crew neck, a front script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew", exposed seam detailing, and a front slit accent along the fitted hem. Complete the look in sleek sunglasses.
Fit & Features
- Cap sleeves
- Crew neck
- Exposed seam detailing
- Graphic script that reads, " Motorcycle/Born to Ride/LA/CA Rider Crew"
- Front slit accent, fitted hem
- Form-hugging fit, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1318
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Totally Favored Denim Trucker Jacket
Your new favorite denim trucker jacket has arrived! It features long sleeves with elasticized cuffs, a collared neckline, four button-down front closures, flap pockets, and a cropped cinch drawstring hem. Complete the look in a basic top and sleek shorts.
Fit & Features
- Long sleeves, elasticized cuffs
- Collared neckline
- Four button-down front closures
- Flap pockets
- Cropped cinch drawstring hem
- Denim fabrication, no stretch
- Fits true to size
Style Number/Barcode: 06203-0466
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Heavenly Chic Mesh Cherub Corset
Look like absolute perfection in this mesh corset featuring a strapless neckline, flexible boning inserts, a cherub printed mesh overlay, and back hook-eye closures. Complete your chic look in a sleek mini skirt and heels.
Fit & Features
- Strapless neckline
- Flexible boning inserts
- Cherub printed mesh overlay
- Cropped hem
- Back hook-eye closures
- Fits true to size
Style Number/Barcode: 06001-4438
Category Name: Vacation Looks
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance