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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Beach Goddess Crochet Lace-Up Maxi Dress
She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.
Fit & Features
- Crochet lined fabric
- V-neckline
- Spaghetti straps
- Open lace-up back design
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000072
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Versatile Basic Rib Knit Crop Top
Your new favorite basic to create all sorts of showstopping outfits! This rib knit crop top features long sleeves, a scoop neck, and a fitted hem. Complete the look in a plaid skirt, jacket, and booties for the perf autumn vibe!
Fit & Features
- Long fitted sleeves
- Scoop neckline
- Fitted cropped hem
- Soft and stretchy
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06002-1438
Category Name: Vacation Looks
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Warm Embrace Cable Knit Sweater
Cozy up on chilly autumn days in this cable knit sweater featuring the perfect oversized fit, long sleeves with ribbed cuffs, a mock neckline with a trendy cutout, and a relaxed hem. Complete the look in leggings and cute suede boots.
Shop More Styles: The Sweater Collection
Fit & Features
- Long sleeves, ribbed cuffs
- Mock neckline with cutout
- Oversized silhouette
- Relaxed fit hem
- Cable knit design
- Fits true to size
Style Number/Barcode: 06005-1452
Category Name: Vacation Looks
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Always Chic Over-The-Knee Slouch Boots
Your look will always be chic in these bold over-the-knee boots! They feature a slouched design, a pointed toe, a sleek stiletto heel, and an inner zipper closure. Pair with a corset top and a faux leather skirt and strut in style!
Fit & Features
- Over-the-knee fit
- Slouched design
- Pointed toe
- Stiletto heel
- Zipper closure
- Faux leather material, smooth lining
- Runs true to size
Style Number/Barcode: 07402-0830
Category Name: Vacation Looks
Price: $30.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fabulous Diva Leopard Print Faux Fur Coat
Layer on this ultra-soft faux fur coat to showcase fabulous diva energy! The coat features a lapel collar, long sleeves, lined side pockets, a relaxed silhouette, and an all-over trendy leopard print pattern. The faux fur fabric includes a knit lining. Style with knee-high boots.
Fit & Features
- Lapel collar
- Long sleeves
- Lined side pockets
- Relaxed fit
- Leopard print
- Faux fur fabric, knit lining with minimal stretch
- Runs true to size
Style Number/Barcode: 06201-0322
Category Name: Vacation Looks
Price: $21.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stacked On Style Lace-Up Boots
Stack on the style with boots that dare to go bold! The faux suede boots feature an over-the-knee shaft length, a sexy bungee strap lace-up back, an inner zipper closure, a pointed toe, and a sleek stiletto heel. Complete the look with a sweater and mini skirt for a dinner date!
Fit & Features
- Over-the-knee shaft length
- Lace-up bungee strap back
- Inner zipper closure
- Pointed toe
- Stiletto heel
- Faux suede material
- Runs true to size
Style Number/Barcode: 07402-0825
Category Name: Vacation Looks
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chill Tale Corduroy Faux Sherpa Shacket
This tale is as chill as time! The corduroy shacket offers a cozy and cute look to bundle up in this season. It features long sleeves, button cuffs, a hooded neckline, four-pocket styling, a button-down front, and a longline hem with faux sherpa lining. Complete the look in knee-high boots.
Fit & Features
- Long sleeves, button cuffs
- Hooded neckline
- Four-pocket styling
- Button-down front
- Longline hem
- Corduroy fabric, faux sherpa lining, no stretch
- Fits true to size
Style Number/Barcode: 06201-0307
Category Name: Vacation Looks
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Knit Distress Crop Sweater
The perfect knit crop sweater to level up your autumn closet! The crew neck sweater features long sleeves and a hem with distressed accents on a purl knit fabric. Complete your trendy look in high-rise jeans and booties for everyday styling!
Fit & Features
- Long sleeves and hem with distressed accents
- Crew neck
- Cropped length
- Purl knit design
- Fits true to size
Style Number/Barcode: 06005-1548
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Femme Edge Platform Lug Booties
Play up your edgy female energy in these faux leather booties featuring a trendy utility design, a round toe, block heel, chunky platform lug sole, knit side panels, and inner zipper closure on an ankle-length shaft. Complete the look in a cool moto jacket!
Fit & Features
- Round toe
- Block heel
- Chunky platform lug sole
- Side knit panels and inner zipper closure
- Ankle-length shaft
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1559
Category Name: Vacation Looks
Price: $12.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cold Babe Plaid Blanket Scarf
You can still be a babe and brace for the cold thanks to this cozy plaid blanket scarf! It features a trendy fringe edge design on cozy and soft fabric. Complete the look in a trendy jacket for a coffee run.
Fit & Features
- Plaid pattern
- Fringe edge design
- Soft and cozy fabric
Style Number/Barcode: 07305-0431
Category Name: Vacation Looks
Price: $3.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Best Of Friends Color Block Sweater
You and this cozy sweater will be the best of friends! The sweater top features color block long sleeves, a crew neck, a ribbed-knit design, and a relaxed fit hem. Complete the look in skinny jeans.
Fit & Features
- Color block long sleeves
- Crew neck
- Relaxed silhouette
- Ribbed-knit design
- Comfortable and soft fabric
- Fits true to size
Style Number/Barcode: 06005-1521
Category Name: Vacation Looks
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The OG Rock Babe Slash Graphic Tee
Flaunt your original status as a rock babe in this edgy graphic tee featuring short sleeves, a crew neck with a V-cut notch, a slashed hem, and a front script that reads, "The Original Rock N Roll". Complete the look in sleek faux leather shorts for a concert!
Fit & Features
- Short sleeves
- Crew neck
- V-cut notch
- Slashed crop hem
- Front script that reads, "The Original Rock N Roll"
- Graphic detailing
- Cotton-blend fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1428
Category Name: Vacation Looks
Price: $6.97 $21.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Jay High-Rise Wide Leg Jeans By Windsor Denim
Easy, breezy, and effortlessly cool slip into the Jay jeans by Windsor denim designed to showcase your edgy-cute style! They feature a flattering high-rise waist, front distressed accents, and knee rips along the wide-leg silhouette. The jeans are crafted from a medium wash with vintage-inspired color fading for the perfect worn-in fit and feel. Complete the look in sleek pointed-toe booties.
Fit & Features
- High-rise waist
- Front distressed accents, knee rips
- Wide-leg silhouette
- Hidden front five-button fly
- Five-pocket styling, belt loop accents
- Medium wash denim, color fade effect
- Runs true to size
Style Number/Barcode: 06602-0380
Category Name: Vacation Looks
Price: $6.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Look Back At Me Cable Knit Top
Watch head-turn as you walk by in this fab cable knit sweater top featuring a sleeveless mock neck, a flirty open-back design, and a cropped hem. Pair with skinny jeans and booties for a fall festival!
Fit & Features
- Sleeveless mock neck
- Open-back design
- Cropped hem
- Cable knit sweater fabric
- Soft and comfortable
- Fits true to size
Style Number/Barcode: 06005-1673
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sultry Bloom Floral Mesh Tube Top
Serve a sultry vibe in this blooming floral printed mesh tube top! Designed with ruched side seams to show off your curves, style with the matching maxi skirt for a gorgeous look.
Shop Matching Bottoms: Sultry Bloom Floral Mesh Maxi Skirt
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Strapless straight neckline, no-slip strip
- Ruched side seams
- Mid-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06001-5714
Category Name: Vacation Looks
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Sheer mesh fabric with knit lining, high stretch
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Dreamy Date Vibes Satin Cropped Blouse
Get a dreamy-chic look for date night with this sleek satin cropped blouse! It features a deep V-neckline with a wrap-front, long peasant sleeves with smocked hems, a lace-up back design, and a cropped, form-hugging fit. The lightweight woven satin fabric has no stretch. Style with faux leather pants and heels.
Fit & Features
- V-neckline, wrap-front
- Long peasant sleeves, tapered smocked hems
- Lace-up back design, tie closure
- Cropped hem, form-hugging fit
- Woven satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1831
Category Name: Vacation Looks
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Press Pause Faux Leather Corset Bodysuit
You'll wanna press pause cause you'll be obsessed with how you slay in this faux leather corset bodysuit perfect for a night out. It features a sleeveless sweetheart neckline, adjustable and detachable spaghetti straps, ruched bust, fitted bodice, and mesh thong bottom with dual snap-button closures. Complete the look in straight-leg jeans.
Fit & Features
- Sleeveless sweetheart neck
- Adjustable and detachable spaghetti straps
- Ruched bust, back zipper closure
- Corset-style fitted bodice
- Mesh thong bottom, dual snap-button closure
- Faux leather non-stretch lined fabric
- Runs true to size
Style Number/Barcode: 06003-1972
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rock Babe Lace-Up Graphic Dress
If you're a rock babe this graphic short dress is the one for you! It features short sleeves, a crew neck, a front lace-up placket, and graphic detail with a script that reads, "Rock N Roll World Tour" along the fitted hem. Complete the look in over-the-knee boots.
Fit & Features
- Short sleeves
- Crew neck
- Front lace-up placket
- Graphic detail/ front reads, "Rock N Roll World Tour"
- Short and fitted hem
- Jersey knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1459
Category Name: Vacation Looks
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Cropped Denim Trucker Jacket
Layer on the casual vibes with this vintage-inspired cropped denim trucker jacket. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, side pockets, and a cropped fit. Style over a basic tee with distressed jeans.
Fit & Features
- Collared neckline
- Drop shoulder design, long sleeves, single button detailing
- Button-down front
- Buttoned chest pockets, side pockets
- Cropped
- Denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 06203-0473
Category Name: Vacation Looks
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Winter Strolls Fringe Scarf
This ultra-soft lightweight scarf is perfect for staying cozy on outdoor strolls this winter season. It features an oblong design with fringe detailing at the hems. The faux wool material has no stretch. Style with lace-up boots.
Fit & Features
- Oblong design
- Fringe detailing
- Soft faux wool material, no stretch
Style Number/Barcode: 07305-0425
Category Name: Vacation Looks
Price: $4.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wrap Me In Plaid Fringe Scarf
Layer on this plaid scarf to brace for the cold weather ahead! It features a fringe edge design on super soft and cozy fabric. Complete the look in a cute shacket and jeans.
Fit & Features
- Plaid pattern
- Fringe edge design
- Soft and cozy fabric
Style Number/Barcode: 07305-0432
Category Name: Vacation Looks
Price: $1.97 $15.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Strut In Style Over-The-Knee Boots
Strut in style in these sleek faux leather over-the-knee boots. They feature an almond-shaped toe, a tall block heel, an inner zipper closure, and a tie-back detail at the top. Pair with a bodycon dress and a moto jacket.
Fit & Features
- Over-the-knee design
- Almond-shaped toe
- Block heel
- Partial inner zipper closure
- Tie-back detail
- Faux leather material
- Runs true to size
Style Number/Barcode: 07402-0811
Category Name: Vacation Looks
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Safari Babe Zebra Cowl Midi Dress
Go on safari looking like a total babe in this zebra midi dress sure to make you in charge of the animal kingdom! It features a sleeveless cowl neckline, dual spaghetti straps, and a form-hugging silhouette. Complete the look in strappy mules for brunch!
Fit & Features
- Sleeveless cowl neckline
- Dual spaghetti straps
- Form-hugging silhouette
- Midi-length hem
- Zebra print
- Knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05101-2026
Category Name: Vacation Looks
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knit Girl Cold Shoulder Sweater
If you're a girl who loves her knit sweaters this one is for you! The cold shoulder sweater features cozy long sleeves with ribbed cuffs, a turtle neckline, a relaxed fit, and a cropped hem ribbed knit fabric. Complete the look in a skirt and knee-high boots.
Fit & Features
- Long sleeves, ribbed cuffs
- Turtle neckline
- Cold shoulder accents
- Relaxed fit
- Cropped hem
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 06005-1588
Category Name: Vacation Looks
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance