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 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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Sultry Cutouts Fitted Bodysuit
Stun in this sultry fitted bodysuit that was made for a night out! It features a trendy mock neckline, a single long fitted sleeve, a top asymmetrical cutout, a side cutout, and a thong bottom. Style this bodysuit with faux leather pants and clear mules.
Fit & Features
- Mock neckline
- Single long fitted sleeve
- Top asymmetrical cutout
- Side cutout at the waist
- Thong bottom, dual snap button closure
- Form-hugging fit, brushed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06001-3959
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Energy Strapless Floral Mesh Maxi Dress
Bring major energy in this strapless floral mesh maxi dress design to flaunt your figure in a bodycon fit and show some skin with a high-side slit. Pair with mules.
Fit & Features
- Floral print, mesh fabric, soft and stretchy knit lining
- Strapless neckline
- High-side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-4074
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Season Long Sherpa Coat
'Tis the season to bundle up and stay cozy! This long faux sherpa coat features a collared neckline, long sleeves, a button-down front, and a relaxed and comfortable fit. Layer this adorable coat over your fave sweater dress and complete the look with knee-high boots.
Fit & Features
- Collared neckline
- Long sleeves
- Complete button-down front, tortoise-shell colored buttons
- Dual front pockets
- Relaxed fit
- Faux sherpa fabric, smooth lining, no stretch
- Runs true to size
Style Number/Barcode: 06201-0280
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chill Vibes Denim And Corduroy Jacket
Layer on the chill vibes with this cute and casual jacket! It features a collared neckline, long sleeves, a button-down front, a frayed hem, and a relaxed fit. The jacket is composed of denim and corduroy fabrics for a trendy look. Style it with a basic tee, jeans, and classic sneakers.
Fit & Features
- Collared neckline
- Long sleeves, single-button details
- Complete button-down front
- Dual buttoned chest pockets
- Frayed hem
- Denim and corduroy fabrics, no stretch
- Runs true to size
Style Number/Barcode: 06204-1081
Category Name: Vacation Looks
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Glam Cabby Hat
Bring elevated glam vibes to your look with this chic cabby hat! It features a traditional cabby hat design with a short brim and a sleek chain-link detail. The tweed material has a stylish metallic thread woven throughout. Pair this hat with hoop earrings.
Fit & Features
- Traditional cabby hat design
- Short brim
- Chain and stud details
- Tweed material, metallic thread detailing
- Smooth woven lining
Style Number/Barcode: 07302-0451
Category Name: Vacation Looks
Price: $6.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Fab Leopard Gloves
Keep it trendy and fab with gloves that are perf for those chilly days. The gloves feature a leopard print and fleece lining. The index finger and thumb feature exterior nylon lining that makes it easy to use phones, tablets, and more without having to remove gloves. Complete the look with a trench and boots.
Fit & Features
- Leopard print
- Fleece lining
- Exterior nylon lining at index and thumb
- Knit fabric
Style Number/Barcode: 07304-0014
Category Name: Vacation Looks
Price: $5.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lady In Faux Fur Cuff Gloves
Look and feel fab in these faux fur cuff gloves featuring a 5-finger design with 'magic touch tips' for using your touch screen device comfortably. Complete the look in a chic coat.
Fit & Features
- Faux fur cuffs
- 5-finger design
- Magic touch tips for using a touch screen
- Comfortable and warm
- Fits true to size
Style Number/Barcode: 07304-0013
Category Name: Vacation Looks
Price: $5.97 $12.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Chic High Slit Slip Dress
Keep it effortlessly chic in a slip dress that stuns with ease. The dress features a sleeveless V-neck, spaghetti straps, a flirty high side slit on the slip-styled silhouette, and a midi length. The dress is composed of a lightweight woven nylon fabric that offers a relaxed fit with minimal stretch. Complete look with mules and a dainty chain necklace.
Fit & Features
- Sleeveless V-neck, spaghetti straps
- Bra-friendly
- Slip-styled silhouette
- Midi length, high side slit
- Lightweight woven fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 05101-1310
Category Name: Vacation Looks
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Steal The Spotlight Leopard Slit Midi Dress
Steal the spotlight looking so fierce in this leopard midi dress! It features a sleeveless V-neckline, spaghetti straps, a flowy midi-length hem, and a front slit perfect for showing off some skin. Style with a pair of strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length hem, flowy silhouette
- Front slit
- Leopard print
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4306
Category Name: Vacation Looks
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flannel Weather Plaid Shacket
It's officially flannel weather and this plaid shacket is just the ticket! It features cozy long sleeves with button cuffs, a collared neckline, button-flap pockets, and a button-down front. The shacket is composed of a soft-woven fabric with no stretch. Complete the look in skinny jeans.
Fit & Features
- Button cuffed long sleeves
- Collared neckline
- Button-flap pockets
- Button-down front
- Plaid pattern, soft-woven fabric, no stretch
- Fits true to size
Style Number/Barcode: 06204-1272
Category Name: Vacation Looks
Price: $15.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Trendsetter Snake Envelope Crossbody
Create a major trendsetting moment with a crossbody that elevates your style. The crossbody features a snake print, an envelope-shaped body, a fold-over closure, and a chain shoulder strap. Complete look with a trench dress and boots.
Fit & Features
- Snake print
- Rectangular-shape
- Envelope fold-over closure
- Hidden front pocket
- Chain shoulder strap
- Faux leather material
Style Number/Barcode: 07203-0840
Category Name: Vacation Looks
Price: $8.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Snow Sparkle Rhinestone Pom Beanie
Sparkle a snowy day in this rhinestone beanie featuring a faux fur pom, cable knit design, and a sherpa lining for extra warmth. Complete your look with a cozy sweater.
Fit & Features
- Faux fur pom
- Rhinestone detailing
- Cable knit design
- Sherpa lining
Style Number/Barcode: 07302-0458
Category Name: Vacation Looks
Price: $2.97 $11.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Butterfly Chain Detail Panama Hat
Add a touch of trendy glamour to your fall look with this adorable Panama hat. It features a wide flat brim adorned with a dainty butterfly charm chain. Style this hat with sleek hoop earrings.
Fit & Features
- Wide flat brim
- Rhinestone butterfly charm chain
- Faux wool material
Style Number/Barcode: 07302-0457
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Velvet Burnout Tie-Front Top
Show up in style in this chic detailed tie-front top. It features long bishop sleeves, an open front with a tie closure creating a flattering V-neckline, and a cropped, form-hugging fit. The sheer mesh fabric features an all-over velvet burnout floral pattern. Complete the look with faux leather pants and mules.
Fit & Features
- Long bishop sleeves, elastic cinched hems
- Open front, tie closure
- V-neckline
- Cropped, form-hugging fit
- Sheer mesh fabric, velvet burnout floral pattern
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06202-0253
Category Name: Vacation Looks
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutie Spotted Leopard Pom Beanie
Look and feel cute in this leopard beanie featuring a pom on the top and a ribbed, foldable cuff. Complete the look with a cozy sweater and leggings.
Fit & Features
- Leopard pattern
- Pom on the top
- Ribbed, foldable cuff
- Knit fabric
Style Number/Barcode: 07302-0439
Category Name: Vacation Looks
Price: $5.97 $13.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetest Day Scoop Neck Ruffle Eyelet Skater Dress
The sweetest days are spent in this eyelet skater dress soaking up the sun with pretty details like sheer trim designs and a ruffled mini-length hem.
Fit & Features
- Eyelet lace fabric, stretchy knit lining
- Scoop neckline, ruffle trim
- Adjustable spaghetti straps
- Sheer trim designs on the bodice
- Ruffled tier mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3936
Category Name: Vacation Looks
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Ryder Rhinestone Panama Hat
Add a touch of glam to your western fit in this panama hat featuring a rhinestone band, wide brim, on faux wool material. Complete the look with a denim jacket.
Fit & Features
- Rhinestone band
- Wide brim
- Faux wool material
Style Number/Barcode: 07302-0454
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Glamour Rhinestone Panama Hat
Showcase trendy glamour with this sparkly detailed Panama hat. It features a traditional Panama hat design, a wide brim, and a rhinestone embellished band. The hat is composed of a faux wool material. Style it with a chic blazer and hoop earrings.
Fit & Features
- Traditional Panama hat design
- Wide brim
- Wide rhinestone embellished band
- Faux wool material
Style Number/Barcode: 07302-0453
Category Name: Vacation Looks
Price: $5.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simply Stylish Faux Wool Boater Hat
This basic faux wool boater hat has a simple yet chic style, making it a perf addition to your fall look. It features a short flat brim, a flat top, and a ribbon band accent. Pair this hat with a faux leather jacket.
Fit & Features
- Short flat brim
- Flat top
- Ribbon band
- Faux wool material
Style Number/Barcode: 07302-0428
Category Name: Vacation Looks
Price: $6.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cuddle Up Knit Blanket Scarf
Cuddle up in a scarf that warms up your look! The scarf features an oversized style and a short fringe. The scarf is composed of a soft-to-the-touch knit fabric that offers a relaxed fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Oversized style
- Short fringe
- Cashmere-like knit fabric
Style Number/Barcode: 07305-0360
Category Name: Vacation Looks
Price: $3.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual-Cozy Long Line Plaid Shacket
Layer on this casual-cozy shacket for an effortlessly stylish look! It features a collared neckline, long sleeves, a complete button-down front, hidden side pockets, and a long line silhouette with a relaxed fit. Wear this shacket with ankle booties.
Fit & Features
- Collared neckline
- Long sleeves, double button details
- Button-down front
- Hidden side pockets
- Long line silhouette, relaxed fit
- Woven fabric, no stretch, plaid print
- Runs true to size
Style Number/Barcode: 06204-1257
Category Name: Vacation Looks
Price: $19.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cozy Plush Plaid Scarf
Cozy on up in this plush woven scarf that will go with your everyday winter looks. It features a cute plaid print with neutral tones, fringe detailing at the hems, and an oversized blanket fit. Style this soft woven scarf with a sweater dress and booties.
Fit & Features
- Plaid print
- Neutral tones
- Fringe detailing
- Oversized blanket fit
- Woven fabric, no stretch
Style Number/Barcode: 07305-0365
Category Name: Vacation Looks
Price: $2.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chill Out Plaid Shacket
Chill out in a cozy shacket to layer over your looks this season! The shacket features a collared neckline, a multi-button down front, two chest pockets, long sleeves, and a long line length. The shacket is composed of a brushed faux wool fabric that offers a relaxed fit with minimal stretch. Complete look with distressed jeans and ankle booties.
Fit & Features
- Collared neckline
- Multi-button down front
- Two chest pockets
- Long sleeves
- Longline length, plaid print
- Faux wool fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 06204-1278
Category Name: Vacation Looks
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rhinestone And Pearl Luxe Knit Beanie
Bring the luxe with a beanie that adds that sparkling touch to your outfit. The beanie features a knit body, faux pearl accents, rhinestones, and a faux fur pom pom accent. Complete look with a sweater and high waist jeans.
Fit & Features
- Knit material
- Faux pearl accents
- Rhinestones
- Faux fur pom pom accent
Style Number/Barcode: 07302-0391
Category Name: Vacation Looks
Price: $7.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free