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.

  • Keep It Lowkey Hoops

    Downplay the drama with some simple lowkey hoop earrings. With their thin etched design and easy latch closure, they provide comfortable wear. A definite must-have for happy hour with your girls! Wear them with a flirty midi dress and some trendy clear mules.

    Fit & Features

    • Dainty textured shimmer design
    • Latch closure

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-0113

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Night Moves Sequin Mini Skirt

    Own the night in this dazzling sequin mini skirt for a chic shimmer!

    Fit & Features

    • Sequin embellished
    • Low-rise waist
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06401-0749

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild Style Zebra Print Crop Top

    Show off a wild style in this trendy zebra print crop top! It features a sleeveless halter neckline with tie-back spaghetti straps, an angled cropped hem, and a form-hugging fit. Complete the look with the matching mini skirt and pair of clear heels.

    Shop Matching Bottoms: Wild Style Zebra Print Mini Skirt

    Fit & Features

    • Sleeveless halter neckline
    • Tie-back spaghetti straps
    • Angled cropped hem
    • Form-hugging fit
    • Zebra print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4697

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Floral Knit Maxi Dress

    Showcase your beauty as the best-dressed wedding guest in this blooming floral knit maxi dress! Designed with a gorgeous floral print design, it features a sleeveless V-neckline, spaghetti straps that lead to a bold open back with a lace-up strappy design, a thigh-high front slit to show off your heels, and a slim-fit silhouette. Complete your look with sleek hoop earrings.

    Fit & Features

    • Floral printed knit fabric
    • V-neckline, spaghetti straps
    • Open back, cross-back lace-up straps
    • Fitted floor-length skirt
    • High front slit
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05101-0851

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Resort Paradise Crochet Open Back Maxi Dress

    Escaping to a resort paradise? You're going to need this crochet maxi dress to give you the perfect getaway vibes! It features a sleeveless crew neckline, an open back design that turns heads, and a form-hugging maxi silhouette with dual side slit accents. Complete the look with sandals and your favorite sunnies!

    Fit & Features

    • Sleeveless crew neckline
    • Open back design
    • Form-hugging silhouette
    • Maxi-length, dual side slit accents
    • Sheer crochet fabric
    • Runs true to size

    Style Number/Barcode: 06005-1829

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On Island Time Strapless Floral Romper

    This strapless romper exudes carefree vibes, perfect for vacations! The strapless neckline and form-hugging fit accentuate your curves, while the statement floral print adds a touch of tropical essence.

    Fit & Features

    • Stretchy knit fabric, statement floral print
    • Strapless neckline
    • Form-hugging fit
    • Ruffled hem, fitted knit shorts
    • Runs true to size

    Style Number/Barcode: 06503-000053

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Iconic Basic Cap Sleeve Midi Dress

    An iconic basic midi dress your closet needs! Create effortlessly chic looks with this knit dress featuring cap sleeves, a V-neck, and a bodycon silhouette with a curved hemline on brushed stretchy fabric. Style with slide sandals and sunglasses for hanging downtown with friends!

    Fit & Features

    • Cap sleeves
    • V-neck
    • Bodycon silhouette
    • Curved midi-length hemline
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-2530

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wild Card Leopard Floral Print Maxi Skirt

    This skirt’s got plot twist energy—sweet florals meet fierce leopard in a ruffled maxi made for your wild side. Let the bold print and thigh-high slit steal the spotlight from brunch to beach nights.

    Fit & Features

    • Sheer mesh fabric with mini-length knit lining, high stretch
    • Leopard and floral multi-print pattern
    • High-rise waist
    • Ruching, hip-hugging fit
    • Thigh-high side slit, ruffled hem
    • Maxi-length hem, flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06501-000061

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: LEOPARD

    Available Size: XS, S, M, L

  • Summer Fling Heart-Shaped Sunglasses

    Flirt up a storm in these adorable heart-shaped sunglasses perf for the summer season. They feature a heart-shaped design with no frame, pink gradient-tinted lenses, sleek metal arms, and rubber nose pads for support. Style with rhinestone hoops.

    Fit & Features

    • Heart-shaped design, no frame
    • Pink gradient-tinted lenses
    • Thin metal arms
    • Rubber nose pads
    • 100% UV protection

    Style Number/Barcode: 07008-1036

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Big Mood Tortoiseshell Oversized Sunglasses

    Giving off that “who is she?” energy in the best way. These oversized sunglasses bring effortless cool to your sunny day 'fits, from pool hangs to city strolls.

    Fit & Features

    • Oversized square-shaped design
    • Tortoiseshell thin metal frame
    • Thin arms
    • Flexible rubber nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000051

    Category Name: Vacation Looks

    Price: $2.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Cute Energy Strapless Paisley Satin Crop Top

    This paisley satin crop top is the easiest way to add a cute boho vibe to your look! The strapless neckline and tie-back closure provide a flattering fit, while the stretchy smocked lining offers comfort and the crop hem flaunts your figure. Complete the look in cute jean shorts and sandals.

    Fit & Features

    • Paisley print, satin fabric, stretchy smocked lining
    • Strapless neckline
    • Tie-back closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2550

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Sensational Smooth Knit Maxi Dress

    Rise to the occasion looking sensational in this basic smooth knit maxi dress perfect for dressing up or down! It features a sleeveless scoop neck, sleek spaghetti straps, a bodycon silhouette, and a flirty back-slit accent composed of double-lined smooth knit fabric. Complete the look in lucite mules for a bridal shower or casual party!

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Bodycon silhouette
    • Back slit accent
    • Maxi-length hem
    • Double-lined smooth knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5158

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Sun Tropical Tie Front Crop Top

    The perfect tropical crop top to enjoy the island sun on vacation! Featuring a V-neckline, adjustable spaghetti straps, and a trendy tie-front design, this top is perfect for warm weather while the cropped hem and tropical print add a touch of flirty fun! Complete the look with the matching bottoms.

    Shop Matching Bottoms: Island Sun Tropical High Rise Palazzo Pants

    Fit & Features

    • Tropical print, knit fabric
    • Adjustable spaghetti straps
    • V-neckline
    • Tie front design
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5160

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Refresh Flocked Mesh Mini Dress

    This chic mini dress will refresh your wardrobe for the season! It features a sleeveless V-neckline, adjustable spaghetti straps for a customized fit, all-over ruching for a flattering look, a mini-length hem, a bodycon silhouette that will hug your curves, and a flocked velvet design in a pretty scroll pattern on mesh fabric. Style this mini-length dress with rhinestone fringe earrings and platform heels.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • All-over ruching
    • Mini-length hem, bodycon fit
    • Flocked velvet design, scroll pattern
    • Sheer mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2384

    Category Name: Vacation Looks

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Era Oversized Square Sunglasses

    Enter your trendy era with these fabulous oversized shades! The sunglasses feature an angled square-shaped design with a plastic frame, built-in nose pads, a sleek gold metal nose bridge, small studded accents on each side, and ombre-tinted lenses. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Oversized angled square-shaped design
    • Plastic frame
    • Built-in nose pads
    • Gold metal nose bridge
    • Small studded accents
    • Ombre-tinted lenses

    Style Number/Barcode: 07008-1092

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Forward Chiffon Puff Sleeve Skater Dress

    Spring forward and add this adorable skater dress to your wardrobe! The short dress features a square neckline with ruching at the bust, short puff sleeves, an empire waist seam, an open back with a tie-back accent, and a short skater skirt with a flirty fit and flare silhouette. The airy chiffon fabric provides a lightweight feel. Style with strappy mules.

    Fit & Features

    • Square neckline, ruched bust
    • Short puff sleeves, elastic cinched hems
    • Empire waist seam
    • Open back, tie-back accent
    • Short skater skirt, fit and flare silhouette
    • Sheer chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2024

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stun And Only Mock Neck Floral Mesh Mini Dress

    Leaving people speechless is easy with this floral mesh mini dress! Crafted from a mesh fabric showcasing a cute floral print perfect for mixing it up this season. This dress features sheer fitted long sleeves with slit flare cuffs, a stylish mock neck, and a flattering bodycon fit. The mini-length hem adds a touch of sass to this stunning dress. Complete the look in stiletto heels.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Mock neck
    • Sheer long sleeves with slit flare cuffs
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5698

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Vine Lace Trim Rose Print Bustier

    Stop and smell this romantic rose print bustier to dress up your favorite bottoms. The delicate lace trim neckline and straps create a stunning silhouette, while the fitted crop hem gives you a flattering look.

    Fit & Features

    • Rose print, eyelet woven fabric, sewn-in woven lining
    • Lace trim sweetheart neckline
    • Lace trim adjustable shoulder straps
    • Hidden front hook and eye closures
    • Stretchy smocked back panel
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000014

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Ditsy Floral Eyelet Strapless Mini Dress

    Keep your summer brunch vibe sweet and stylish in this floral eyelet strapless mini dress! The airy lightweight eyelet knit fabric is detailed with a flirty ditsy floral print and features a brushed knit lining for coverage. The mini-length dress is shaped with a strapless straight-across elasticized neckline for added stretch and a bodycon silhouette to highlight your curves. Pair with espadrille wedges and a mini handbag.

    Fit & Features

    • Ditsy floral print
    • Stretchy eyelet knit fabric with knit lining
    • Strapless straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5800

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Party Scene Sweetheart Mini Dress

    Steal the scene at every party in this sweetheart mini dress! It features a sleeveless sweetheart neckline, a padded underwire bust tie-shoulder straps, a bodycon silhouette, and side and back ruched seams to accentuate your curves. The smooth knit fabric offers plenty of stretch. Style this mini-length dress with chic earrings.

    Fit & Features

    • Sleeveless sweetheart neckline, padded underwire bust
    • Tie-shoulder straps
    • Back zipper and hook-eye closure
    • Short, bodycon silhouette
    • Side and back ruched seam
    • Knit fabric, lined bodice, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-5259

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stroll The Beach V-Neck Floral Paisley Maxi Dress

    Wherever your summer travels take you, always be in style with this casual floral paisley maxi dress! Featuring adjustable spaghetti straps and a stretchy smocked V-neckline, you'll have the perfect fit for a day in the sun. The crisscross back adds a playful touch, while the ruffled hem gives a flirty flair to the flowy silhouette. Complete the look with a cute hair accessory and sandals!

    Fit & Features

    • Floral paisley print, woven fabric, stretchy knit lining
    • Adjustable spaghetti straps, crisscross back
    • Stretchy smocked V-neckline
    • Flowy silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5566

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girly Twirl Bow Short Sleeve Tee

    Twirl your hair and bring the aesthetic with this adorable short sleeve tee perfect for coquette girlies! This tee features short sleeves and a crew neckline, embroidered bow adds a touch of sass, while the fitted crop hem and stretchy rib knit fabric create a flattering silhouette. Complete the look in a lace trim mini skirt.

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Embroidered bow
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1836

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sparkly Flirt Satin Heatstone Corset

    Sparkly and flirty, add this femme satin corset for a stunningly sultry vibe! It features a sleeveless, sweetheart neck, adjustable spaghetti straps, underbust support, and flexible boning inserts along the bodice with all-over heatstone embellishments. Complete the look in wide-leg pants and heels.

    Fit & Features

    • Sleeveless, sweetheart neck, adjustable spaghetti straps
    • Underbust support
    • Flexible boning inserts
    • All-over heatstone embellishments
    • Cropped hem
    • Back hook-eye closures
    • Sleek satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-2059

    Category Name: Vacation Looks

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Shadow Blooms Floral Skater Dress

    Delicate and dainty, unveil this skater dress for every soiree this season! The short dress features breezy peasant long sleeves, a sweetheart neckline, a padded bust, a smocked back, and a fit and flare silhouette with a ruffled short hem. The dress is designed with a floral jacquard pattern on an airy fabric with a smooth woven lining and no stretch. Complete the look with espadrille wedges for a baby or wedding shower!

    Fit & Features

    • Peasant long sleeves, elastic cinched hems
    • Sweetheart neckline, padded bust, smocked back
    • High waist seam, fit and flare, skater silhouette
    • Short-length hem
    • Floral jacquard pattern
    • Airy fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2604

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance