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.

  • Breezy Boho Sheer Lace Asymmetric Maxi Skirt

    Channel an effortless boho vibe in this breezy sheer lace maxi skirt featuring a high-rise waist, ruched detailing with an adjustable drawstring, a high-cut side slit, and an asymmetric hem with a flowy silhouette. Perfect for pairing with a crop top and booties.

    Fit & Features

    • Sheer lace fabric with mini-length knit lining, plenty of stretch
    • High-rise waist
    • Ruching, adjustable drawstring
    • High side slit
    • Asymmetric maxi-length hem
    • Flowy fit
    • Runs true to size

    Style Number/Barcode: 06501-1065

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

  • Daytime Cheer Fit And Flare Ruffle Floral Dress

    Spread daytime cheer in this fit and flare floral dress! Made from soft chiffon fabric, this dress is adorned with a ditsy floral print for a whimsical touch.  This playful dress features a sweetheart neckline with ruffle trim, adjustable spaghetti straps, and a charming keyhole bust tie. The stretchy smocked waist and tiered ruffled hem create a flattering fit and flare silhouette. Complete the look with a cute purse and sandals!

    Fit & Features

    • Ditsy floral print, chiffon fabric, stretchy knit lining
    • Ruffle trim sweetheart neckline
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5447

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Duo Halter Polka Dot Crop Top

    Look and feel so delightful in this polka dot halter crop top for an effortlessly poised look for brunch or parties! Pair with the matching skirt.

    Fit & Features

    • Polka dot print, woven-lined fabric
    • Halter neckline, lace trim, spaghetti strap tie, metal insert
    • Padded bra cups
    • Back zipper and hook-eye closure
    • Flexible boning
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Skirt: Delightful Duo Polka Dot Ruffle Skirt

    Style Number/Barcode: 06003-2747

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Turn Heads Tie-Dye Open Back Maxi Dress

    Serving body, back, and bold energy! This mesh maxi turns heads with a sultry cowl halter, hoop details, and a tie-dye print that does the most in the best way.

    Fit & Features

    • Tie-dye print, mesh fabric, stretchy knit lining
    • Cowl halter neckline
    • Hoop inserts, tie-back straps
    • Open back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000115

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: PINK

    Available Size: XS, S, M

  • Casual Style Icon Cutout Bodycon Midi Dress

    This sultry-chic midi dress will level up your look and make you a casual style icon! It features a sleeveless asymmetric one-shoulder neckline with a tank strap, a bold asymmetric waist cutout for a hint of skin, a midi-length hem, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Pair with clear mules.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Tank strap
    • Asymmetric waist cutout
    • Midi-length hem
    • Bodycon silhouette
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5201

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Lovin' Crochet Knit Mini Dress

    You'll love the summer vibes this crochet knit mini dress brings to your happy hour look. Designed with a strapless neckline and sultry side slit, the bodycon fit will flaunt your stunning curves.

    Fit & Features

    • Sheer crochet knit fabric with knit lining, moderate stretch
    • Strapless straight-across neckline
    • Ruched side seam, adjustable drawstring, side slit
    • Mini-length asymmetric hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000046

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Elevated Trouser Shorts

    Refresh your wardrobe with these chic and elevated trouser shorts! They feature a high-rise waist, a front button closure, front pleated detailing, and a fitted silhouette. The smooth crepe fabric includes a woven lining. Style with the matching blazer.

    Shop Matching Ivory Blazer: Chic And Elevated Woven Blazer

    Shop Matching Pink Blazer: Bold Moves Woven Blazer

    Shop Matching Turquoise Blazer: Bold Moves Woven Blazer

    Fit & Features

    • High-rise waist
    • Front button, hidden button and zipper closure
    • Front pleating
    • Front pockets
    • Fitted
    • Crepe fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0263

    Category Name: Vacation Looks

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Mood Strapless Tropical Knit Jumpsuit

    This eye-catching tropical knit jumpsuit will put you in the mood for a beachy vacay! Designed with a stretchy knit fabric with a multi-colored tropical print pattern, this jumpsuit will bring the bold allure to your dreamy getaway. It features a strapless straight-across neckline, a fitted high waist for a snatched look, and a relaxed wide-leg silhouette. Style with chunky gold hoops and strappy sandals.

    Fit & Features

    • Stretchy knit fabric, bust lining
    • Tropical print
    • Strapless straight neckline
    • Fitted high waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2454

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Way She Moves Striped Bra Top

    This striped bra top has entered the girl's vacay chat! Boasting a sexy plunge neckline and cutout back, you'll be the hit of the trip. Pair with the matching skirt to complete the look!

    Shop Matching Bottoms: Way She Moves Striped Midi Skirt

    Fit & Features

    • Striped print, scalloped trim, stretchy knit fabric
    • Plunge V-neckline
    • Wide shoulder straps
    • Cutout back with tie closure
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2258

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Sweetheart Mesh Mini Dress

    You'll be such a stunning sweetheart in this gorgeous mesh mini dress! Featuring a flattering ruffled padded sweetheart neckline with an off-the-shoulder design and a curve-hugging fit with all-over ruched detailing, this dress is perf for your next date night with bae. Pair with some clear lucite heels for that it-girl look.

    Fit & Features

    • Off-the-shoulder neckline, short sleeve cuffs
    • Sweetheart neck, built-in padded bust
    • Ruffle trim detailing, all-over ruching
    • Back zipper and hook and eye closure
    • Short, form-hugging fit
    • Sheer mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1539

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coolest Look Aviator Metal Sunglasses

    Make any outfit cool in these aviator sunglasses! They feature a sleek metal frame, smoke-tinted lense to help protect your eyes, and rubber nose supports and arms for comfort. Complete the look in trendy sandals.

    Fit & Features

    • Aviator sunglasses
    • Sleek metal frames
    • Smoke-tinted lense
    • Rubber nose supports and arms

    Style Number/Barcode: 07008-1101

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Beauty Tropical Print Halter Top

    Show off your beauty on your next vacay in this sleek knit halter top with a trendy O-ring bust accent and an alluring tropical palm leaf print.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Tropical palm leaf print
    • Sleeveless V-neckline, bust O-ring accent
    • Halter strap
    • Partially open back
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000089

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S

  • Sweet And Spicy Scoop Neck Mini Dress

    Sweet and spicy, this mini dress is exactly what your next club night needs! It features a sleeveless scoop neckline, dual spaghetti straps, a strappy back design, and side ruched seams to accentuate your curves along the short bodycon silhouette. Complete the look in eye-catching stiletto heels.

    Fit & Features

    • Sleeveless scoop neckline
    • Dual spaghetti straps
    • Strappy back design
    • Side ruched seams, bodycon silhouette
    • Mini-length hem
    • Slinky knit fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4804

    Category Name: Vacation Looks

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Getaway Tropical Print Maxi Skirt

    This alluring tropical print maxi skirt will create a gorgeous getaway look! Designed with a trendy tropical print pattern on the airy mesh fabric, it features a high-rise waist, a maxi-length hem with a sultry high-cut side slit, and a slim-fit silhouette. Style with the matching crop top for your next destination vacay!

    Shop Matching Top: Gorgeous Getaway Tropical Print Crop Top

    Fit & Features

    • High-rise waist
    • Maxi-length hem
    • High-cut side slit
    • Slim-fit silhouette
    • Tropical print
    • Sheer mesh fabric, full-length knit lining
    • Runs true to size

    Style Number/Barcode: 06501-0956

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Perfectly Striped Shirt Skater Dress

    Step out in this perfectly striped shirt dress to look cute for picnics in the park, family gatherings, or graduations! It features long sleeves with buttoned cuffs, a collar v-neckline, a corset-seam illusion waist, a cutout lace-up back design, and a short skater silhouette. Complete the look with teardrop earrings.

    Fit & Features

    • Long sleeves, buttoned cuffs
    • Collar v-neckline
    • Corset-seam illusion waist
    • Cutout lace-up back design
    • Skater silhouette, short-length hem
    • Striped print, poplin non-stretch woven fabric
    • Runs true to size

    Style Number/Barcode: 05102-5048

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Sight Strapless Ruffled Eyelet Mini Dress

    You'll be the sweetest sight in this strapless eyelet mini dress as the lovely bride-to-be or birthday girl! The strapless neckline and flexible boning provide a comfortable and flattering fit, while the tiered ruffled mini-length hem adds a playful touch. Complete the look with earrings and strappy block heels.

    Fit & Features

    • Eyelet woven fabric, sewn-in knit lining
    • Strapless neckline
    • Back zipper and hook-eye closure
    • Flexible boning inserts
    • Tiered ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3042

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Girl Halter Open Back Tropical Mini Dress

    Getaway to paradise in this tropical mini dress! Featuring a sultry cowl halter neckline and an open back with dual spaghetti strap ties, this dress will show plenty of skin on vacay while the bodycon silhouette and mini-length hem flatter your figure. Complete the look with doorknocker earrings and heels.

    Fit & Features

    • Tropical print, mesh fabric lined with stretchy knit
    • Halter cowl neckline
    • Open back with dual spaghetti strap ties
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5795

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Muse Lace-Up Embroidered Crop Top

    Channel that boho babe vibe in this lace embroidered crop top with a trendy lace-up front design. Style with the matching mini skirt for festival season!

    Shop Matching Bottoms: Boho Muse Lace Embroidered Mini Skirt

    Fit & Features

    • Lined sheer mesh fabric with lace embroidery
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Front lace-up design
    • Smocked back, zipper closure
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2746

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Like A Daydream Lace Ruffle Skater Dress

    Arrive on the scene like a daydream in this lace skater dress with flirty ruffles and mini-length hem that'll get you all the compliments!

    Fit & Features

    • Lace knit fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4156

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: M, L

  • Flutter Away Layered Skater Dress

    Flutter away in a twirl-worthy skater dress! The dress features a sleeveless wrap V-neckline, adjustable spaghetti straps, and a tiered skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with mules and dainty rings.

    Fit & Features

    • Sleeveless V-neckline, wrap-front design
    • Adjustable spaghetti straps
    • Back zipper, hook and eye closure
    • Tiered skater skirt
    • Chiffon fabric, knit lining, minimal stretch
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-1458

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Like Me Sleeveless Ruffled Maxi Dress

    An effortless woven maxi dress for shower celebrations, graduations, or meet-ups with the girls! It boasts a flowy ruffled silhouette and a floor-length hem perfect for styling with cute sandals.

    Fit & Features

    • Cotton fabric, woven lining
    • Square neckline
    • Adjustable spaghetti straps
    • Flowy ruffled silhouette
    • Maxi-length floor hem
    • Runs true to size

    Style Number/Barcode: 05102-6022

    Category Name: Vacation Looks

    Price: $54.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • Just One Night Ruched Midi Dress

    Make your night out a fab one with a dress that stuns! The dress features a sleeveless cowl neckline, spaghetti straps, curve-defining ruche detail, and a high-side slit for a display of leg along the midi-length hem. The dress is composed of a smooth knit fabric that offers a moderate stretch. Complete the look with mules. 

    Fit & Features

    • Sleeveless cowl neckline, sticky bra recommended
    • Spaghetti straps
    • Ruching, high side slit
    • Midi length hem
    • Form-hugging fit
    • Smooth knit fabric, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1107

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In My Feels Scoop Neck Bra Top

    Whether you're on vacay or sitting poolside, this scoop neck bra top will have you feeling yourself! Pair with the matching skirt.

    Fit & Features

    • Stretchy knit fabric
    • Spaghetti straps
    • Scoop neckline
    • Ultra-cropped hem
    • Runs true to size

     

    Shop The Matching Skirt: In My Feels High-Rise Midi Skirt

    Style Number/Barcode: 06005-2257

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

    Product Badge:
    • Sale
  • Fierce Summer Vibes Rhinestone Fishnet Mini Dress

    Layer on this fab rhinestone fishnet mini dress over short dresses, bodysuits, or swimsuits to give off fierce summer vibes! It features a crew neckline, short sleeves, a mini-length hem, a form-hugging fit, and all-over sparkling iridescent rhinestone embellishments on the sheer unlined fishnet fabric. Complete the look with sleek hoop earrings.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Mini-length hem
    • Form-hugging fit
    • Mini iridescent rhinestone embellishments
    • Sheer unlined fishnet fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4766

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale