Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • 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: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • 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
  • Sun Coast Dream Paisley Bodycon Slit Maxi Dress

    Enjoy a vacay or day out by the sunshine coast in this paisley maxi dress with a flattering bodycon fit and side slit for effortless movement!

    Fit & Features

    • Paisley boho print, mesh fabric, sewn-in brushed knit lining
    • Square neckline
    • Spaghetti straps, criss cross back
    • Bodycon silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5928

    Category Name: Vacation Looks

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    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: In Stock

    Available Color: IVORY

    Available Size: L

  • Own the Bloom Floral Strappy Halter Maxi

    Bloom like you mean it. This floral maxi dress turns heads with a plunge strappy neckline, open back, and form-hugging fit that was made to steal the spotlight.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Strappy plunge halter neckline, tie straps
    • Open back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000034

    Category Name: Vacation Looks

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Hot In The Tropics Tropical Bodycon Mini Dress

    Walk around looking hot in this tropical bodycon mini dress while on a resort vacation or island destination! 

    Fit & Features

    • Tropical palm print, knit fabric, stretchy knit lining
    • Scoop neckline
    • Spagehtti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000101

    Category Name: Vacation Looks

    Price: $19.97 $28.90

    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: $20.97 $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
  • 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
  • Cute Direction Pointelle Skater Mini Dress

    With a cute pair of sandals and this pointelle skater mini dress, everyone will be talking about what a cutie you are! 

    Fit & Features

    • Pointelle knit fabric
    • Scoop neckline, wide shoulder straps
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2267

    Category Name: Vacation Looks

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

  • 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
  • Blossomed Babe Floral Halter Midi Dress

    You'll blossom looking like a babe in this floral chiffon midi dress at every dressy soiree! . The stunning halter neckline features an eye-catching stone insert that draws attention, while the flowy midi-length hem creates a graceful silhouette.

    Fit & Features

    • Floral print, chiffon lined fabric
    • Halter neckline, stone insert, spaghetti strap tie-back closure
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4040

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: TAUPE

    Available Size: S, M

    Product Badge:
    • Sale
  • 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: $19.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S

    Product Badge:
    • Sale
  • 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: $19.97 $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
  • Cutest Ever Flutter Sleeve Mini Dress

    This airy chiffon mini dress designed with short flutter sleeves and a flowy A-line silhouette would be the cutest brunch style! You'll adore the subtle swiss dot pattern and dainty lace trim hem.

    Fit & Features

    • Sheer chiffon fabric, swiss dot pattern, woven lining, lace trim
    • Sleeveless scoop neckline, ruched bust
    • Adjustable spaghetti straps, flutter sleeve accent
    • Back zipper closure, tie-back design
    • Mini-length A-line silhouette, pleating
    • Runs true to size

    Style Number/Barcode: 05101-000078

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • 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
  • Sweet Look Eyelet Knit Skater Dress

    Capture hearts with your sweet look in this airy eyelet knit skater dress. You'll adore the flowy feel of the fit-and-flare silhouette.

    Fit & Features

    • Eyelet knit fabric with knit lining
    • Sleeveless square neckline, underbust seam
    • Adjustable spaghetti straps
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6001

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: 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