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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Taking The Plunge Floral Mesh Crop Top
Take the plunge to flaunt this floral mesh crop top this spring! With adjustable drawstring straps and ruched seams that accentuate your figure, this top will receive many compliments.
Fit & Features
- Floral print, mesh fabric, brushed knit lining
- Plunge neckline
- Adjustable drawstring shoulder straps
- Side ruched seams
- Fitted crop hem
- Runs true to size
Style Number/Barcode: 06001-000091
Category Name: Vacation Looks
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cinched And Chic Faux Leather Trench Coat
Create a chic cinched silhouette with this sleek faux leather trench coat. Featuring a lapel collar, long sleeves, an off-center zip-front, a belted waist, and a fitted silhouette, this jacket will amp up your winter 'fits. Layer over a sweater dress with knee-high boots.
Fit & Features
- Lapel collar, long sleeves
- Off-center zip-front
- Single chest pocket flap
- Belted waist, rectangular buckle
- Fitted silhouette
- Faux leather material, sewn-in woven lining
- Runs true to size
Style Number/Barcode: 06204-1520
Category Name: Vacation Looks
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Latest And Greatest Seamless Zip-Up Catsuit
Check out the latest seamless catsuit for the greatest vibe of all time! It features fitted long sleeves, a crew neckline with a zip-up closure, a form-hugging fit, and a skinny-leg design on seamless knit fabric with plenty of stretch. Complete the look in a trendy puffer jacket for a coffee run and errands!
Fit & Features
- Fitted long sleeves
- Crew neckline
- Zip-up closure
- Form-hugging fit
- Skinny-leg design
- Seamless knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 07109-0339
Category Name: Vacation Looks
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Western Chic Chain Trim Cowboy Hat
Top off your festival-ready outfits with this western chic cowboy hat! Made from a faux wool material, it features a structured top, upturned sides, and a textured metal accent trim to add that trendy touch. Includes adjustable ties hidden on the inside for a tighter fit. Style with a tank top, denim skirt, and booties!
Fit & Features
- Faux wool material
- Structured top
- Upturned sides
- Textured metal accent chain trim
- Adjustable ties for tighter fit
Style Number/Barcode: 07302-1548
Category Name: Vacation Looks
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easily Stunning Cutout Striped Midi Dress
This cutout striped midi dress was made for a laidback babe like you! With a bodycon fit and dual side slits for effortless allure, this dress is perfect for vacation or strolling the beach.
Fit & Features
- Striped print, stretchy knit fabric
- V-neckline with cutout
- Adjustable spaghetti straps
- Bodycon silhouette
- Dual side slits
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-2290
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Muse Mode Abstract Print Midi Tube Dress
Giving art gallery energy but make it flirty. This abstract print midi tube dress is stretchy, lined, and made to turn sidewalks into runways—perfect for girls’ night, date night, or that “just because” moment.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Abstract print
- Strapless straight-across neckline
- Midi-length hem
- Fitted silhouette
- Runs true to size
Style Number/Barcode: 05101-000404
Category Name: Vacation Looks
Price: $45.90
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Perfection Ribbed Knit Mini Dress
This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Square neckline
- Long fitted bell sleeves, flared hems
- Mini-length hem, form-hugging fit
- Ribbed knit fabric, knit lining, plenty of stretch
- Style runs small
Style Number/Barcode: 05102-5217
Category Name: Vacation Looks
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Girl Abstract Halter Slit Maxi Dress
Need an unforgettable look? This abstract maxi dress will be the perfect companion for rooftop cocktails and parties, boasting a sultry halter neckline, cutout bodice, and high slit giving major sultry energy.
Fit & Features
- Abstract print, stretchy knit fabric, short knit stretch lining
- Halter neckline with tie straps, hoop insert
- Cutout bodice
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000003
Category Name: Vacation Looks
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute In Crochet Long Sleeve Sweater
Perfect for any season, this crochet sweater can be styled as a coverup or worn with a cute bralette or fitted tank. It's designed with long bell sleeves and a relaxed fit, this sweater adds a boho charm to any look.
Fit & Features
- Sheer crochet fabric
- Boat neckline
- Long bell sleeves
- Relaxed fit
- Runs true to size
Style Number/Barcode: 06005-000027
Category Name: Vacation Looks
Price: $26.90
Availability: Out of Stock
Product Badge:- Ships Free
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So Loved Tube Bodycon Midi Dress
Love at first wear...this tube midi dress elevates your everyday look with curve-accentuating side ruched seams, a bodycon fit, and a side slit for movement.
Fit & Features
- Stretchy rib knit fabric, knit lining
- Strapless tube neckline
- Side ruched seams
- Bodycon silhouette
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000309
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: BLACK, IVORY
Available Size: XS, S, M, L, XL
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Dancing Shoes Rhinestone Short Block Heels
Put on your dancing shoes aka these gorgeous block heels for a night of twirling! They feature an open almond-shaped toe, a strappy rhinestone-embellished foot strap with a knot accent, a short block heel, an adjustable rhinestone trim ankle strap with a buckle closure, and a metallic sheen. Complete the look with a sparkly clutch purse for a dressy or formal soiree!
Fit & Features
- Open almond toe
- Strappy rhinestone-embellished foot strap, knot accent
- Short block heel
- Adjustable rhinestone trim ankle strap, buckle closure
- Metallic sheen
- Faux leather luxe fit cushioned insole
- Runs true to size
Style Number/Barcode: 07401-4536
Category Name: Vacation Looks
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual And Cozy Off-The-Shoulder Sweater Dress
This on-trend sweater dress is the casual and cozy staple you need this fall and winter season. It features a chic off-the-shoulder neckline, long sleeves, a short-length hem, and a relaxed fit. The ribbed sweater knit fabric offers a moderate stretch. Pair this sweater dress with over-the-knee boots for a stylish and elevated look.
Fit & Features
- Off-the-shoulder neckline
- Long sleeves
- Short-length hem
- Relaxed silhouette
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1764
Category Name: Vacation Looks
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chill Days Ombre Striped Knit Cardigan
This adorable and cozy striped knit cardigan is perfect for those chill laidback days! It features a V-neckline, a complete button-down front, long balloon-style sleeves with tapered hems, a relaxed fit, and a trendy ombre striped pattern on the ribbed sweater knit fabric. Complete your cute and casual look with distressed jeans and ankle boots.
Fit & Features
- V-neckline
- Complete button-down front design
- Long balloon sleeves, tapered hems
- Relaxed fit
- Ombre striped pattern
- Ribbed sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1878
Category Name: Vacation Looks
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetheart Status Tube Midi Dress
She’s sculpted, strapless, and made to serve. This textured midi dress brings the heat with a sweetheart neckline, front cutout, and curve-hugging fit—perfect for date nights, rooftop vibes, or that one party everyone’s posting about.
Fit & Features
- Texture knit fabric, smooth knit stretchy lining
- Strapless sweetheart tube neckline with notch cutout
- Mini bust cutout
- Back zipper and hook-eye closure
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000047
Category Name: Vacation Looks
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Winter Beauty Wool Trench Coat
Hey beauty! Bundle up in this posh wool trench coat that will elevate your winter look. It features a collared neckline, long sleeves, a partial button-down front, and a long line silhouette. Layer this coat over a sweater dress and complete the outfit with over-the-knee boots.
Fit & Features
- Lapel collar
- Long sleeves
- Partial snap button-down front
- Faux front pockets
- Long line silhouette
- Wool exterior, woven lined interior, no stretch
- Runs true to size
Style Number/Barcode: 06201-0253
Category Name: Vacation Looks
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Going Places Lace-Up Knit Maxi Dress
A knit maxi dress to pack in your suitcase for vacations or weekend escapes! The dress is designed with a trendy lace-up back and a bodycon silhouette that hugs your curves.
Fit & Features
- Texture knit fabric, knit lining
- High crew neckline
- Spaghetti straps
- Lace-up back
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-2297
Category Name: Vacation Looks
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laid-Back Chic Collared Cropped Sweater
Give off a laid-back chic look for your weekend plans in this cute cropped sweater! Designed from a cozy ribbed sweater knit fabric, it features a fold-over collared neckline, a partial zip-front design, slouchy long sleeves with tapered hems, and a cropped hem. Style with the matching shorts for the perf lounge vibe!
Shop Matching Bottoms: Laid-Back Chic High Waist Shorts
Fit & Features
- Fold-over collared neckline
- Partial zip-front
- Slouchy long sleeves, tapered hems
- Cropped hem
- Ribbed sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1925
Category Name: Vacation Looks
Price: $15.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Fold-over collared neckline
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Giving Me Cozy Feels Eyelash Surplice Sweater
This cute surplice sweater will give you cozy feels! With its long sleeves and V-neckline, this top is designed for easy layering. The twisted surplice bodice adds a special touch, while the soft, eyelash knit fabric offers comfort. Complete the look in jeans and boots for a classic winter style!
Fit & Features
- Long sleeves
- V-neckline
- Surplice twisted bodice
- Cropped hem
- Soft eyelash knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1919
Category Name: Vacation Looks
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Want To Want Me Floral Crochet Tie Front Top
Wrap yourself in the bohemian charm of this floral crochet top! With kimono half sleeves and a tie-front design, this top is perfect for adding a touch of boho vibes to any outfit.
Fit & Features
- Sheer floral crochet knit fabric
- Kimono half sleeves
- Tie-front
- Crop hem
- Runs true to size
Style Number/Barcode: 06204-000010
Category Name: Vacation Looks
Price: $39.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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All Things Cute Cable Knit Sweater Dress
Wrap yourself up in this cute and casual cable knit sweater dress perfect for pumpkin patches or festivals! It features long sleeves with banded cuffs, a plunge surplice V-neckline and V-cut back, a tie-waist belt, and a short form-hugging fit. Complete the look in trendy knee-high boots.
Fit & Features
- Long sleeves, banded cuffs
- Plunge surplice V-neckline, V-cut back
- Tie-waist belt
- Form-hugging fit
- Short-length hem
- Cable knit design, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5370
Category Name: Vacation Looks
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Full Of Trendiness High-Rise Fray A-Line Maxi Skirt
Your summer is sure to be full of trendiness with this high-rise maxi skirt perfect for weekend plans! Featuring a high-rise waist and unique A-line silhouette with frayed trim, this skirt is made from soft and comfortable cotton woven fabric. Complete the look in an off-the-shoulder blouse and booties!
Fit & Features
- Cotton woven fabric, slight stretch
- High-rise waist
- Hidden side zipper and hook-eye closure
- Frayed A-Line silhouette
- Maxi-length
- Runs true to size
Style Number/Barcode: 06301-0192
Category Name: Vacation Looks
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Treat Chenille Crop Sweater
Your new go-to chenille sweater for the fall to winter months is here! It features slouchy long sleeves, ribbed cuffs and crew neck, a relaxed silhouette, and cropped hem with dual asymmetrical slit accents. Complete the look in high-rise jeans for looking at Christmas lights!
Fit & Features
- Slouchy long sleeves
- Ribbed cuffs and crew neckline
- Relaxed silhouette
- Cropped hem, asymmetrical slit accents
- Chenille knit fabric
- Soft and comfortable
- Fits true to size
Style Number/Barcode: 06005-1574
Category Name: Vacation Looks
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Attraction Ditsy Floral Mini Dress
You're sure to have a natural attraction to this ditsy floral mini dress - perfect for a casual birthday or afternoon tea! It features a sleeveless scoop neck, spaghetti straps, a flirty tie front, and ruched bust, and a bodycon silhouette. Style with lace-up heels for a statement finish!
Fit & Features
- Sleeveless scoop neck
- Spaghetti straps
- Tie front and ruched bust
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4938
Category Name: Vacation Looks
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Edge It Up Faux Leather Biker Boots
Edge up your fall 'fits with this pair of trendy faux leather biker boots. They feature an above-the-ankle height with a square toe, dual straps with buckle accents, a low block heel for comfortable wear, and are made from a smooth faux leather material. Style these biker boots with a bomber jacket and hoop earrings.
Fit & Features
- Above-the-ankle height
- Square toe
- Dual buckled straps
- Low block heel
- Faux leather material
- Runs true to size
Style Number/Barcode: 07403-1718
Category Name: Vacation Looks
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance