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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Talk About Breezy Chiffon Crop Top
Styling this chiffon crop top will be such a breeze! The top features peasant sleeves with ruffled cuffs, pleated shoulder details, a ruched sweetheart neckline, a built-in padded bust with overlay, and a back zipper and hook-eye closure. Complete the look in best-selling skinny jeans.
Fit & Features
- Peasant sleeves, ruffled cuffs, pleated shoulders
- Ruched sweetheart neckline
- Built-in padded bust with an overlay
- Cropped hem
- Back zipper and hook-eye closure
- Lined chiffon crepe non-stretch fabric
- Fits true to size
Style Number/Barcode: 06003-1962
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wrapped In Chic Vibes Satin Maxi Skirt
Get wrapped in chic vibes in this sleek satin maxi skirt! It features a high-rise waist with ruched detailing, a faux wrap-front design creating a high front slit, a maxi-length hem that hits right above the ankle, and a curve-hugging silhouette. Style with a cropped bustier and clear heels.
Fit & Features
- High-rise waist, ruching
- Hidden back zipper closure
- Faux wrap-front design, high front slit
- Maxi-length hem
- Curve-hugging fit
- Woven satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06401-0562
Category Name: Vacation Looks
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Glam Strides Rhinestone Strap Heels
Take your next glamorous strides in these luxe faux leather heels featuring a sleek square toe, dual PVC straps with rhinestone embellishment, and a lucite stiletto heel with a flat geo-shaped bottom. The heels showcase a chic metallic sheen. Style with stunning jewelry set to complete the dressy look!
Fit & Features
- Square toe
- Dual PVC straps, rhinestone embellishments
- Lucite stiletto heel, flat geo-shaped bottom
- Metallic sheen
- Faux leather material
- Runs true to size
Style Number/Barcode: 07401-4164
Category Name: Vacation Looks
Price: $4.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Just A Peek Crew Neck Keyhole Top
Attract all the attention by showing off just a peek of your skin! This elevated basic crop top features fitted long sleeves, a crew neck with hidden hook and eye closures, and a keyhole cutout accent atop the surplice bodice on stretchy rib-knit fabric. Style with straight-leg jeans to complete your trendy look!
Fit & Features
- Fitted long sleeves
- Crew neck
- Hidden front hook and eye closures
- Keyhole cutout accent
- Surplice bodice, cropped hem
- Rib-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1524
Category Name: Vacation Looks
Price: $6.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rendezvous In Satin Slip Midi Dress
Have a chic rendezvous in this satin slip midi dress featuring a sleeveless V-neck, bungee spaghetti straps, a fitted a-line silhouette, and a sultry front slit along the hem. The dress is composed of smooth, non-stretch satin fabric. Complete the look in lace-up stiletto heels.
Fit & Features
- Sleeveless V-neck
- Bungee spaghetti straps
- Fitted a-line silhouette
- Front slit
- Midi-length hem
- Non-stretch woven satin fabric
- Runs true to size
Style Number/Barcode: 05101-2383
Category Name: Vacation Looks
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Meant To Be Lace Up Corset Top
This corset top is meant to be in your lineup this season! Add a sultry touch to your everyday look in this strapless top featuring flexible boning inserts along the cropped bodice and an eye-catching lace-up back for a customized fit. Style with wide-leg pants for cocktail hour!
Fit & Features
- Strapless and sleeveless
- Flexible boning inserts
- Cropped hem
- Lace-up back, tie closure
- Woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06003-2179
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Perfectly Pleated Cuffed Trouser Pants
Achieve a chic, polished look with these perfectly pleated cuffed trouser pants. They feature a high-rise waist, belt loops, front pockets, crisp pleated detailing near the waist, a straight-leg fit, and a cuffed hem. Elevate the look of these smooth woven pants with a cropped blouse and clear mules.
Fit & Features
- High-rise waist, belt loops
- Hidden front zipper, button, and hook and bar closures
- Front pockets
- Pleating
- Straight-leg fit, cuffed hem
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06402-0506
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Diva Faux Fur Collar Jacket
Even divas want to be cozy and cute on their off-duty days! Keep it chic in this faux fur jacket featuring long sleeves, a collared neckline, an open-front design, hidden side pockets, and a mid-length hem. Style with best-selling shoes to complete the look!
Fit & Features
- Long sleeves
- Collared neckline
- Open-front design
- Hidden side pockets
- Mid-length hem
- Faux fur fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0374
Category Name: Vacation Looks
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Delicate Beauty Six-Pack Earrings Set
Dainty and delicate, adorn your ears with these beautiful earrings! The six-pack set features pairs of two in assorted styles perfect for everyday or formal styling. Complete the look in glitzy block heels for a celebration!
Fit & Features
- Six-pack earring set with lobster clasp closures
- One metal studs
- One rhinestone studs
- One faux pearl studs
- One geo-shaped studs
- One chain-twist hoop studs
- One dangly chain studs
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1449
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Whimsical Statement Flower Earrings
Add these charming and whimsical statement earrings to your look! They feature a large flower design with rhinestone embellishments and a post-back closure. Style with a chic ring set.
Fit & Features
- Flower design
- Rhinestone embellishments
- Post-back closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1454
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Nautical Charm Flower Huggies
The perfect blend of nautical and charm! These huggie earrings feature rhinestone flower charms on a sleek metal half-hoop with an omega closure. Complete the look in a cute denim jacket for a day date.
Fit & Features
- Rhinestone flower charm
- Sleek half-hoop
- Omega closure
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1453
Category Name: Vacation Looks
Price: $2.97 $9.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bringing The Heat Abstract Cutout Mini Dress
You'll bring the sizzle to every party in this sexy abstract mini dress! The halter neckline with hoop insert adds a trendy touch while the cutout front and bodycon fit make a statement.
Fit & Features
- Abstract print, mesh fabric, stretchy knit lining
- Halter neckline with tie straps, hoop insert
- Front cutout
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-000307
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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It-Girl Layered Chain Necklace Set
Give off that it-girl energy when you accessorize your 'fits with this trendy necklace set. It features a flat chain-link choker necklace and a longer paperclip chain-link necklace detailed with a faux pearl accent and a toggle closure. Style this set with rhinestone stud earrings.
Fit & Features
- Two necklaces
- Flat chain-link choker necklace, adjustable chain, lobster clasp closure
- Longer paperclip chain-link necklace, faux pearl accent, toggle closure
Style Number/Barcode: 07002-1360
Category Name: Vacation Looks
Price: $4.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cool-Girl Layered Charm Necklace Set
Step up your 'fits and achieve that cool-girl style with this trendy layered necklace set! It features a flat chain-link choker necklace and a double-layered dainty chain-link necklace with a rhinestone flower charm and a cascading lariat with rhinestone accents and a mini rhinestone star charm. Pair this necklace set with stud earrings.
Fit & Features
- Two necklaces
- Flat chain-link choker necklace
- Double-layered chain-link necklace
- Rhinestone flower charm
- Lariat, rhinestone accents, rhinestone star charm
- Adjustable chains, lobster clasp closures
Style Number/Barcode: 07002-1366
Category Name: Vacation Looks
Price: $6.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swirls Of Style Satin Midi Dress
Stylish marble swirls capture all the attention on this satin midi dress featuring a sleeveless v-neck, adjustable spaghetti straps, flexible boning inserts along the bodice, and a curve-hugging silhouette with a front slit accent. Complete the look in a casual crop jacket.
Fit & Features
- Sleeveless v-neck, adjustable spaghetti straps
- Flexible boning inserts
- Back zipper and hook-eye closure
- Front slit, curve-hugging, midi-length hem
- Marble print
- Satin fabric, knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4867
Category Name: Vacation Looks
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Little Sassy Platform Block Heels
A little sassy yet completely eye-catching! Rock these faux suede heels with your going-out fit. They feature an open square toe, wide toe strap, a chunky platform sole, triangular block heel, and a closed ankle with lace-up straps. Complete the look with a crop denim jacket.
Fit & Features
- Open square toe, wide toe strap
- Chunky platform sole
- Triangular block heel
- Closed ankle
- Lace-up straps
- Faux suede material
- Runs true to size
Style Number/Barcode: 07401-4177
Category Name: Vacation Looks
Price: $34.90
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Shine Rhinestone Stud And Duster Earrings Set
Show off a chic shine with this effortlessly chic earrings set! The multipack features nine pairs of dainty studs and linear duster earrings in varying rhinestone designs that will give both your casual and dressy looks the prettiest sparkle. Style these earrings with a rhinestone ring set for all the more glamour.
Fit & Features
- Nine pairs of studs and linear duster earrings
- Various rhinestone embellished designs
- Post-back closures, rubber stoppers
Earrings are final sale and may not be returned or exchanged.
Style Number/Barcode: 07001-1521
Category Name: Vacation Looks
Price: $2.97 $14.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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City Girl Plaid Faux Wool Coat
Layer on this plaid faux wool coat for a chic city girl look! It features a lapel collar, an open front, long sleeves, lined side pockets, and a mid-length hem with a fitted silhouette. The all-over plaid print will give your 'fit that classic vibe. Style over a sweater dress with knee-high boots.
Fit & Features
- Lapel collar, open front
- Long sleeves
- Side pockets, smooth lining
- Mid-length hem, fitted silhouette, back slit accent
- Plaid print
- Faux wool fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0315
Category Name: Vacation Looks
Price: $27.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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A Polished Vibe Plaid Faux Wool Coat
Layer on this plaid faux wool coat for a polished vibe! Featuring a lapel collar, an open front, long sleeves, side pockets, a mid-length hem, and a fitted silhouette, this coat is a definite winter staple. The all-over plaid print will keep your looks classic and chic. Style with faux leather ankle booties.
Fit & Features
- Lapel collar, open front
- Long sleeves
- Side pockets, back slit accent
- Mid-length hem, fitted silhouette
- Plaid print
- Unlined faux wool fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0313
Category Name: Vacation Looks
Price: $27.97 $62.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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All The Feels Faux Fur Lined Denim Jacket
Cuddle up in this trendy denim jacket to layer over all of your favorite crop tops and bodysuits! It features a faux fur hood, long sleeves, a multi-button down front, pockets, and a relaxed fit. The denim fabric features an ultra-soft faux fur lining for a warm and cozy feel. Style this jacket with distressed jeans and combat boots.
Fit & Features
- Faux fur hood
- Long sleeves, faux fur cuffs
- Multi-button down front
- Dual buttoned chest pockets, faux side pockets
- Relaxed fit
- Denim fabric, faux fur lining
- Runs true to size
Style Number/Barcode: 06203-0480
Category Name: Vacation Looks
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Coffee First Cable Knit Bodysuit
Got coffee on your mind? Look cute for your run to the shop in this cable knit bodysuit featuring long sleeves, a ribbed mock neck, a form-hugging fit, and a thong bottom with dual snap-button closure. Style with high-rise jeans for the perf look!
Fit & Features
- Long sleeves
- Ribbed mock neck
- Form-hugging
- Thong bottom, dual snap-button closures
- Cable knit design
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1535
Category Name: Vacation Looks
Price: $11.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Fabulous Vibe Faux Fur Crop Jacket
Layer on this luxe faux fur crop jacket for to give off a fabulous vibe! It features a lapel collar, an open front, long sleeves, and a fitted, cropped hem. The ultra-soft faux fur fabric features an all-over illusion stripe design to give the look of a trendy puffer design. Style with a faux leather mini skirt and heels.
Fit & Features
- Lapel collar
- Open front
- Long sleeves
- Fitted, cropped hem
- Soft faux fur fabric, smooth woven lining, no stretch
- Illusion stripe design
- Runs true to size
Style Number/Barcode: 06201-0368
Category Name: Vacation Looks
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Stylishly Edgy Faux Leather Flare Pants
Show off a cool-girl vibe in these stylishly edgy faux leather flare pants! They feature a high-rise waist with a five-pocket and belt loop design, a front button and zipper closure, a hip-hugging fit, and a flared-out hem. The smooth-coated faux leather fabric offers a moderate stretch. Pair with a corset top and clear heels.
Fit & Features
- High-rise waist
- Five-pocket and belt loop design
- Front button, hidden zipper closure
- Hip-hugging fit
- Flared-out hem
- Coated faux leather fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06402-0670
Category Name: Vacation Looks
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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That's My Type Mock Neck Zip Top
This everyday basic is just your type! The long sleeve top features a mock neck, front zipper closure, and a fitted hem on rib-knit fabric. Complete the look in a mini skirt and a jacket.
Fit & Features
- Long sleeves
- Mock neck
- Front zipper closure
- Fitted hem
- Rib-knit fabric
- Fits true to size
Style Number/Barcode: 06002-1498
Category Name: Vacation Looks
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance