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.

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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

  • 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
  • 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
  • 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
  • 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
  • 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