Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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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.

  • What You Want Strappy Cutout Slit Midi Dress

    This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!

    Fit & Features

    • Double-lined rib knit fabric, moderate stretch
    • Spaghetti straps
    • Square neckline
    • Strappy cutout twist back
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5663

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Petals and Plans Floral Lace-Up Maxi Dress

    For date nights, rooftop drinks, or weddings, this floral maxi dress is perfect for every event! The curve-hugging fit, flirty slit, and open lace-up back effortlessly flatters your figure and makes heads turn.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Lace-up open back
    • High front slit
    • Curve-hugging fit, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4160

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L, XL

  • Special Stunner One-Shoulder Cutout Ombre Maxi Dress

    Leave everyone in awe when you're in this ombre maxi dress for sunset cocktails! Featuring a unique one-shoulder neckline with an adjustable spaghetti strap and flirty side cutout, this dress hugs your curves and shows off your legs with a high-side slit along the maxi-length hem and form-hugging silhouette. Complete the look with sparkly bracelets.

    Fit & Features

    • Ombre mesh fabric, stretchy knit lining
    • One-shoulder neckline, adjustable spaghetti strap
    • Side cutout
    • High side slit
    • Form-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5708

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Have It All V-Neck Halter Crop Top

    Care to have it all with this sultry crop top? It boasts a halter V-neckline with a spaghetti strap tie, a low back cut to flaunt some skin, and adjustable side drawstrings let you customize the fit along the cropped hem. Complete the look in women's best-selling bottoms for any casual occasion!

    Fit & Features

    • Knit fabric
    • Halter V-neckline, spaghetti strap tie
    • Low cut back
    • Adjustable side drawstrings
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5353

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Think About Me Lace-Up Floral Skater Dress

    Captivate everyone's thoughts in this floral skater dress sure to be the prettiest pick anyone has ever seen! With a square neckline and spaghetti straps, it's perfect for warmer days. The lace-up back and bow tie adds a playful touch, while the skater silhouette and mini-length hem flatter any figure. Complete the look with an adorable hair bow and sunglasses!

    Fit & Features

    • Floral print, woven fabric lined, no stretch
    • Spaghetti straps
    • Square neckline, bow tie
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5490

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Attraction Toe Ring Strappy Block Heels

    A pair of strappy block heels with a trendy toe ring trim that gives every outfit a sweet look!

    Fit & Features

    • 2.5" Block heel
    • Square toe
    • Strappy design
    • Toe ring trim
    • Luxe fit cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-5260

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: TAN, WHITE, BLACK

    Available Size: 5.5, 6.5, 7, 7.5, 8.5, 10, 6, 9

  • Vacay Mode Tropical Floral Mesh Maxi Dress

    Activate vacay mode and radiate dreamy vibes in this alluring tropical maxi dress! Designed with an airy sheer mesh fabric with a mini-length knit lining, this maxi-length dress is accented with a blooming tropical floral print for a stunning look. It features a sleeveless square neckline, spaghetti straps, ruched detailing at the waist to accentuate your curves, and a bodycon silhouette with a thigh-high side slit to showcase some leg. Style with stiletto heels for a sunset dinner!

    Fit & Features

    • Tropical floral print
    • Sheer mesh fabric with mini-length knit lining, plenty of stretch
    • Square neckline
    • Spaghetti straps
    • Ruched waist, side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5543

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunkissed and Stunned Halter Striped Maxi Dress

    This striped knit maxi brings the heat with a flirty open back, high front slit, and sheer vibes made for beach strolls or rooftop sips.

    Fit & Features

    • Striped texture knit design, sheer fabric
    • Halter plunge neckline, tie straps
    • Open back with tie strap
    • High front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000137

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: L

  • Charming Allure Tie-Front Ruffled Skater Dress

    Captivate with your charming allure in this pretty tie-front ruffled skater dress! Designed with a breezy gauze woven fabric, this short dress is the perfect lightweight style for weekend dates. It features a sleeveless V-neckline with the cutest tie-front bow design, a built-in padded bust, adjustable spaghetti straps so you can find your perfect fit, and a smocked back for added stretch. The high waist flows out to a tiered ruffled skater skirt with an adorable fit-and-flare silhouette. Complete your look with hoop earrings and heeled sandals.

    Fit & Features

    • Gauze woven fabric with woven lining, no stretch
    • V-neckline with tie-front, padded bust
    • Adjustable spaghetti straps
    • High waist, smocked back
    • Tiered ruffled design
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5720

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vibes Tie-Front Crop Top

    This breezy woven crop top will give off those effortless weekend vibes with its flowy short sleeves and tie-front design. Style with the matching wide-leg palazzo pants for a chic look.

    Shop Matching Bottoms: Weekend Vibes Wide-Leg Palazzo Pants

    Fit & Features

    • Woven fabric
    • Plunging V-neckline
    • Tie-front design
    • Short flowy sleeves
    • Cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-000007

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: ORANGE, IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Favorite Fleur V-Neck Floral Chiffon Skater Dress

    Give them a twirl in this adorable floral chiffon skater dress at birthdays or graduation parties! Featuring puff short sleeves, a tie front bust, and a stretch smocked empire waist, this dress will hug your curves in all the right places. The skater silhouette and ruffled hem add a playful touch to this flowy chiffon dress. Complete the look with teardrop earrings.

    Fit & Features

    • Floral print, chiffon fabric lined with stretchy knit
    • V-Neckline, tie front
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3135

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cut to the Chase Halter Jumpsuit

    Serving drama in all the right places. This halter jumpsuit brings the heat with a cutout bodice and a breezy wide-leg fit that’s perf for rooftop parties, sunset dates, or vacay nights out.

    Fit & Features

    • Linen-like woven fabric
    • Halter neckline, spaghetti strap ties
    • Cutout bodice with open tie-back
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000006

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: CORAL

    Available Size: XS, S, M, L

  • Sunny Energy Halter Cut Out Wide Leg Jumpsuit

    Bring the sunny energy in this halter cut-out wide leg jumpsuit wherever you go! This sultry texture knit jumpsuit features a halter spaghetti strap with tie closure for a perfect fit, along with a cutout bust design to show some skin, and a flattering wide-leg silhouette for an easy, breezy style. Complete the look with sunnies and sandals!

    Fit & Features

    • Texture knit stretchy fabric
    • Halter spaghetti strap
    • Cut out bust
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2472

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Chic Mid-Rise Ruffled Shorts

    Effortless for vacay or weekend fun, these chic shorts are designed with a smocked drawstring high-rise waist and a ruffled hem!

    Fit & Features

    • Cotton woven fabric
    • Flowy short sleeves
    • V-neckline
    • Tie-front 
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06303-000008

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK, LIGHT, BLUE, RED, OFF, WHITE

    Available Size: XS, S, M, L

  • Breezy Chic Floral Embroidered Chiffon Skater Dress

    This breezy chic floral chiffon skater dress is perfect for your summer parties! The airy sheer embroidered chiffon fabric is detailed with a dainty floral print and includes a stretchy full-length knit lining. The short dress features a sleeveless sweetheart neckline, a bustier-style bodice with a padded bust and structured underwire, and ruched cups. The adjustable spaghetti straps lead to a partially smocked back design for added stretch with a secure back zipper closure. The front faux buttons lead to a high waist seam flowing out to a short skater skirt with a flirty fit and flare A-line silhouette. Complete your look with strappy sandals.

    Fit & Features

    • Sheer embroidered chiffon fabric, floral print, stretchy knit lining
    • Sweetheart neckline, bustier bodice, padded bust with underwire, ruching
    • Adjustable spaghetti straps
    • Partial stretchy smocked back, zipper with hook and eye closure
    • Front faux buttons, high waist seam
    • Fit and flare A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3009

    Category Name: Vacation Looks

    Price: $49.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready High Rise Crochet Maxi Skirt

    Heading on vacation? Don't forget to grab this vacay ready high-rise crochet maxi skirt with a sultry high front slit that flaunts some leg. Pair with the matching top and your fave shades!

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • High-rise elasticized waist
    • High front slit
    • Flowy maxi-length silhouette
    • Runs true to size 

     

    Shop The Matching Top: Vacay Ready Tie-Front Bandea Crochet Crop Top

    Style Number/Barcode: 06301-0214

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L, XL

  • Romance That Wows Large Blossom Floral Maxi Dress

    Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!

    Fit & Features

    • Large blossoming floral print
    • Mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3343

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be My Forever Ribbon Bow Bodycon Mini Dress

    Flattery will get you everywhere in this sleeveless mini dress perfect for boasting an adorable look! The scoop neckline is adorned with delicate lace and charming bow detail, while the tank shoulder straps give a flirty touch. The bodycon silhouette and mini-length hem finish this flawless dress. Complete the look in platform high heels for a party.

    Fit & Features

    • Woven fabric with minimal stretch
    • Scoop neckline, lace and ribbon trim, bow
    • Back zipper and hook-eye closure
    • Tank shoulder straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5817

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Presence Abstract Floral Mini Dress

    Make a sultry impression in this abstract floral mini dress with an alluring cutout and a ruffled slit design perfect for grabbing cocktails on vacation!

    Fit & Features

    • Abstract floral print, mesh-lined fabric
    • Cowl halter neckline
    • Cutout bodice with hoop insert
    • Bodycon silhouette
    • Ruffled slit design, mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000038

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: L

  • Artsy Flair Strapless Cutout Abstract Mini Dress

    Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Side cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5693

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sure To Love Floral Woven Puff-Sleeve Skater Dress

    You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.

    Fit & Features

    • Floral print
    • Woven fabric with smooth woven lining
    • Ruched scoop neckline with tie-front detail
    • Short puff sleeves with elastic cinched hems
    • Stretchy smocked high waist
    • Fit-and-flare silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5716

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Addiction Mid-Rise Fray Denim Shorts

    Upgrade your denim collection with these mid-rise denim shorts with a trendy frayed hem and perfect vintage-inspired look and feel!

    Fit & Features

    • Medium wash denim
    • Front button and zipper closure, belt loops
    • Five-pocket styling
    • Frayed hem
    • Runs true to size

    Style Number/Barcode: 06603-0508

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: MED, DENIM

    Available Size: S, XL

  • Garden Of Romance Tie Back Rose Floral A-Line Dress

    Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.

    Fit & Features

    • Rose floral print, chiffon fabric lined with stretchy knit
    • Square neckline
    • Adjustable spaghetti straps
    • A-Line silhouette
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3257

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Signature Stripes Strapless A-Line Maxi Dress

    Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.

    Fit & Features

    • Striped pattern, cotton woven fabric, no stretch
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5802

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale