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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Keeping Knit Chic Mock Neck Sweater
Keep your winter wardrobe chic with this trendy knit sweater! Featuring a mock neckline with a V-neck front cutout, long dolman-style sleeves, and a relaxed fit, this sweater can be effortlessly dressed up or down. The knit fabric offers minimal stretch. Pair with denim and sneakers for the day and sleek faux leather leggings and ankle booties for the night.
Fit & Features
- Mock neckline
- V-neck front cutout
- Long dolman sleeves
- Mid-length hem, relaxed fit
- Knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 06005-1601
Category Name: Vacation Looks
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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You're The One Tie-Front Midi Dress
This rib knit midi dress will be the one you'll adore for casual outings and more! The dress features long sleeves, a surplice v-neckline, a faux wrap bust atop a flirty cutout bodice with a tie-front closure, and a bodycon silhouette. Style with faux suede booties for the perf autumn look!
Fit & Features
- Long sleeves
- Surplice v-neckline
- Faux wrap bust
- Cutout bodice, tie-front closure
- Bodycon, midi-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4843
Category Name: Vacation Looks
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Shine Leopard Crop Wrap Top
Shimmer and shine, unveil your wild side in this glitter striped leopard crop top for a night on the prowl. It features dramatic long bell sleeves, a plunge v-neckline, and a wrap-around design so you can customize the style. Complete the look in PVC mules.
Fit & Features
- Long bell sleeves
- Plunge v-neckline
- Customizable wrap-around design
- Cropped hem
- Glitter striped leopard print
- No stretch
- Fits true to size
Style Number/Barcode: 06003-1818
Category Name: Vacation Looks
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Houndstooth Fringe Blanket Scarf
Keep it chic with a scarf that adds a stylish touch to your layered outfits. The scarf features a trendy houndstooth pattern, a short fringe trim, and an oversized blanket style. The scarf is composed of a soft knit fabric. Complete look with a sweater and high waist jeans.
Fit & Features
- Houndstooth pattern
- Short fringe trim
- Oversized blanket style
- Soft knit fabric
Style Number/Barcode: 07305-0339
Category Name: Vacation Looks
Price: $4.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Step It Up Collared Mini Sweater Dress
Step up your everyday fall 'fits with this trendy mini sweater dress. It features a johnny collar, a V-neckline with a partial button-down front, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Style with sleek hoop earrings and knee-high boots.
Fit & Features
- Johnny collar
- V-neckline, partial button-down front
- Long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1534
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sagittarius Graphic Crop Tee
It's your season Sagittarius babes! This graphic crop tee is perfect for your birthday party outfit! The top features short sleeves, a crew neck, and a front script that reads, "Sagittarius/It's The Fire In Me". Complete the look in sleek faux leather shorts and boots!
Fit & Features
- Short sleeves
- Crew neck
- Front script reads, "Sagittarius/It's The Fire In Me"
- Cropped hem
- Jersey knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1499
Category Name: Vacation Looks
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off Duty Chunky Platform Sneakers
Elevate your off-duty streetwear vibe in these chunky platform sneakers boasting high fashion inspiration! They feature an almond toe, front lace-up closure, faux leather and mesh knit detailing, and a rubber grip sole. Complete the look in a cool puffer jacket for a day out with friends!
Fit & Features
- Almond toe
- Front lace-up closure
- Faux leather and mesh knit detailing
- Chunky platform design
- Rubber grip sole
- Runs true to size
Style Number/Barcode: 07407-0213
Category Name: Vacation Looks
Price: $12.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Head-Turning Chic Marble Print Midi Dress
Make heads turn in this eye-catching chic bodycon midi dress! It features a sleeveless square neckline, spaghetti straps, bold front and back waist cutouts, ruched detailing down the side seams, and a midi-length, curve-hugging silhouette. The stretchy knit fabric features an all-over abstract marble print pattern for a trendy vibe. Complete the look with clear heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Front and back waist cutouts
- Ruching down the side seams
- Midi-length hem, fitted bodycon silhouette
- Abstract marble print pattern
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4837
Category Name: Vacation Looks
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Fabulous Faux Fur Knit Duster
Layer on this chic ribbed knit duster for a forever fabulous look! Featuring a removable faux fur collar accent, long fitted sleeves, a tie-front design, and a long-length flowy silhouette, this duster can be dressed up or down depending on your mood! The ribbed knit fabric offers a moderate stretch. Complete your look with ankle booties.
Fit & Features
- Removable faux fur collar, button attachments
- Long fitted sleeves
- Tie-front
- Long-length flowy silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1431
Category Name: Vacation Looks
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lowkey Luxe Rectangle Frame Sunglasses
These sunglasses do not come to play. Sleek, structured, and effortlessly cool, they’re your go-to for effortless throw-on-and-go styling!
Fit & Features
- Sleek rectangular frames
- Tinted lenses
- 100% UV protection
Style Number/Barcode: 07008-000066
Category Name: Vacation Looks
Price: $2.97 $10.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy In The City Faux Sherpa Coat
Feel cozy and look cute for a day in the city slaying it in this faux sherpa coat featuring long sleeves, a collared neckline, single button closure, and a cropped hem. Layer over a basic bodysuit and jeans!
Fit & Features
- Long sleeves
- Collared neckline
- Single button closure
- Cropped hem
- Faux sherpa, smooth woven lining
- No stretch
- Fits true to size
Style Number/Barcode: 06201-0349
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Resort Ready Eyelet Linen Platform Block Heels
Elevate your spring-to-summer looks in these eyelet linen platform block heels, perfect for a resort vacation or weekend event.
Fit & Features
- Block heel
- Square toe, criss cross toe strap
- Platform sole
- Luxe fit cushioned insole
- Adjustable ankle strap, buckle closure
- Eyelet linen material
- Runs true to size
Style Number/Barcode: 07401-5274
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Styled To Perfection Belted Trench Coat
This chic faux wool trench coat will have you styled to perfection! It features a lapel collar, long sleeves, an open front with a tie-front belt to cinch the waist, and a short-length hem with a relaxed silhouette. Layer over a mock neck sweater with your fave pair of denim.
Fit & Features
- Lapel collar
- Long sleeves, faux side pockets
- Open front
- Tie-front belt
- Short-length hem, relaxed fit
- Faux wool fabric, no stretch
- Runs true to size
Style Number/Barcode: 06201-0311
Category Name: Vacation Looks
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Chain Effect Midi Dress With Belt
You'll make a chain reaction by stepping out in this rib knit tank midi dress featuring a sleeveless square neck, tank shoulder straps, a detachable chain belt with lobster clasp closure, and a form-hugging silhouette. Complete the look in a chic blazer for happy hour!
Fit & Features
- Sleeveless square neck
- Tank shoulder straps
- Detachable chain belt with lobster clasp closure
- Form-hugging silhouette
- Midi-length hem
- Double-lined rib knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4882
Category Name: Vacation Looks
Price: $19.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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SoHo Girl Double-Breasted Trench Coat
This faux sherpa trench coat is giving major city vibes! The coat features long sleeves, a lapel collar neckline, double-breasted button closures, side pockets, and a longline hem. Complete the look with a trendy bucket hat for a day spent downtown!
Fit & Features
- Long sleeves
- Lapel collar neckline
- Double-breasted button closures
- Side pockets
- Longline hem
- Faux sherpa, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0353
Category Name: Vacation Looks
Price: $16.97 $79.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Layer On The Luxe Vibes Faux Fur Jacket
Layer on the luxe vibes with this chic faux fur jacket! It features a collared neckline, long sleeves, a zip-front, plush faux fur fabric that is ultra-soft to the touch, seam detailing to give the illusion of a puffer design, lined side pockets, and a fitted silhouette with a cropped hem. The jacket includes a full lining. Style over a basic bodysuit with faux leather pants for an elevated look.
Fit & Features
- Collared neckline
- Long sleeves
- Complete zip-front, lined side pockets
- Plush faux fur fabric, smooth lining, no stretch
- Seam detailing to give the illusion of a puffer design
- Fitted silhouette, cropped hem
- Runs true to size
Style Number/Barcode: 06201-0301
Category Name: Vacation Looks
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Trendy Florals Flocked Velvet Corset Top
Create a head-turning look with this trendy floral corset top! It features a square neckline, long fitted sleeves with slit accents at the hems for a subtle flared-out design, a corset-style bodice with flexible boning, and a cropped, form-hugging fit. The knit fabric features an all-over flocked velvet floral pattern for a chic vibe. Style with faux leather pants and mules.
Fit & Features
- Square neckline
- Long fitted sleeves, slit accents at the hems
- Corset-style bodice, flexible boning
- Back hook and eye closures
- Cropped hem, form-hugging fit
- Flocked velvet floral pattern
- Sheer knit fabric, front knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 06001-4447
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lavish Life Satin Slit Midi Skirt
You'll be living lavishly in your new must-have satin midi skirt perfect for dinner parties, celebrations, and holiday events! The skirt features a sleek high-rise waist, side zipper and hook-eye closure, a curve-hugging silhouette, and a high-cut side slit. Complete the look in a crop sweater and heels!
Fit & Features
- High-rise waist
- Side zipper and hook-eye closure
- Curve-hugging silhouette
- High-cut side slit
- Midi-length hem
- Silky satin fabric, no stretch
- Fits true to size
Style Number/Barcode: 06401-0575
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Total Grudge Lug Sole Loafers
These faux leather loafers are giving major grudge 90s babe vibes! They feature a round toe, chunky lug platform sole, and heel, and are composed of faux leather material. Complete the look in a trendy plaid matching set.
Fit & Features
- Round toe
- Chunky lug platform sole and heel
- Classic loafer style
- Faux leather material
- Runs true to size
Style Number/Barcode: 07405-0036
Category Name: Vacation Looks
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Cool-Girl Vibes Knit Sneakers
Style up these on-trend knit sneakers for a casual cool-girl vibe! They feature a lace-up front with adjustable drawcords, a textured sole, a lightweight knit design, and faux leather accents. Pair with a ribbed knit mini dress and your fave denim jacket.
Fit & Features
- Lace-up front, adjustable drawcords
- Textured sole
- Pull tabs
- Knit design
- Faux leather accents
- Runs true to size
Style Number/Barcode: 07407-0214
Category Name: Vacation Looks
Price: $4.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Icon Cow Faux Fur Long Coat
Unveil an iconic diva status layering on this cow pattern coat and watch every head turn! The faux fur coat features long sleeves, a lapel collar neckline, an open-front design, hidden side pockets, and a relaxed long-length hem. Complete the look in thigh-high boots.
Fit & Features
- Long sleeves
- Lapel collar neckline
- Open-front design
- Relaxed, long-length hem
- Cow pattern
- Faux fur, smooth woven lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0352
Category Name: Vacation Looks
Price: $32.97 $72.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Special Price
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Slay The Chill Quilt Puffer Jacket
Slay the chill and your fit' by layering on this quilted puffer jacket featuring long sleeves with elasticized cuffs, a standing collar neckline, front zipper closure, side pockets, and an adjustable drawcord crop hem. The jacket is composed of nylon-woven fabric with insulation to help keep you warm and protected from the elements. Complete the look in trendy lug boots.
Fit & Features
- Long sleeves, elasticized cuffs
- Standing collar neckline
- Front zipper closure, side pockets
- Adjustable drawcord crop hem
- Nylon-woven quilted fabric
- Insulated and lined
- Fits true to size
Style Number/Barcode: 06201-0329
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Up Cable Knit Oversized Cardgian
Cozy up in this adorable oversized cable knit cardigan for the cutest look! It features an open front, long dolman-style sleeves, dual front pockets, and a relaxed fit. Layer over a basic bodysuit with faux leather pants and ankle booties.
Fit & Features
- Open front
- Long dolman-style sleeves
- Dual front pockets
- Oversized, relaxed fit
- Cable knit fabric, no stretch
- Runs true to size
Style Number/Barcode: 06005-1509
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Real Sweet Colorblock Chenille Sweater
Real sweet and so soft! This color-block chenille sweater will be a cozy staple piece in your closet. It features long dolman sleeves, a crew neck, and a relaxed fit silhouette. The soft chenille knit fabric offers a moderate stretch. Complete the look in basic leggings and boots.
Fit & Features
- Long dolman sleeves
- Crew neck
- Relaxed silhouette
- Color block pattern
- Chenille knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1571
Category Name: Vacation Looks
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free