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.

  • Pretty Taste Tie-Front Printed Satin Top

    Give your look a pretty style with this satin crop top designed with chic short sleeves and a tie-front that flaunts your figure!

    Fit & Features

    • Printed satin woven fabric
    • Short sleeves
    • Tie-front
    • Ultra cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1875

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: PEACH

    Available Size: S, M, L, XL

    Product Badge:
    • Sale
  • Sweetheart Vibes Strappy Back Floral Crop Top

    Get ready for those sweetheart vibes in this strappy floral crop top! This playful top features puff short sleeves and a plunge V-neckline for a flirty touch. The strappy open back with tie closure adds a unique and charming detail, while the cropped hem and rose print fabric make it perfect for any summer occasion. Complete the look with denim jeans.

    Fit & Features

    • Rose floral print
    • Double-lined stretchy knit fabric
    • Plunge V-neckline
    • Strappy back, tie closure
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5187

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendsetter Mid-Rise Belted Twill Skort

    Grab a cute top and this mid-rise skort for a trendsetting outfit of the day! This skort is designed to flatter with a belted mid-rise waist and a bodycon design that accentuates your curves along the mini-length hem.

    Fit & Features

    • Twill woven fabric
    • Mid-rise waist, adjustable belt with buckle closure
    • Bodycon fit
    • Mini-length hem, shorts lining
    • Four-pocket styling, belt loop accents
    • Front hidden hook-eye and zipper closures
    • Runs true to size

    Style Number/Barcode: 06303-000018

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

  • Fall For Me Patent Faux Leather Wedges

    Fall for these patent faux leather wedges perfect for any occasion! Designed with a sleek almond toe, a wedge heel for comfort and elevated style, and a closed ankle with an adjustable ankle strap allows for a perfect fit. Complete the look with a trending handbag.

    Fit & Features

    • 4" Wedge heel
    • Patent faux leather material
    • Adjustable ankle strap with buckle closure
    • Almond toe
    • Runs true to size

    Style Number/Barcode: 07406-0350

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Beauty High Rise Floral Mini Skirt

    Effortlessly embody beauty in this floral mini skirt perfect for spring or summer! The high-rise waist and bodycon fit hug your curves, while the ruched seam and slit add a touch of playfulness to the mini-length hem. Complete the look in a crop top.

    Fit & Features

    • Ditsy floral print, stretchy knit fabric
    • High-rise waist
    • Ruched seam and slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1012

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beauty So Unique Lace-Up Floral Chiffon Maxi Dress

    Give off undeniable grace and beauty in this floral chiffon maxi dress on vacation or at parties! Featuring delicate adjustable spaghetti straps, a V-neckline, and a stunning lace-up back, this dress will accentuate your curves and create a flattering silhouette with a front slit and maxi-length hem. Complete the look in heeled sandals and earrings!

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • Adjustable spaghetti straps
    • V-neckline
    • Lace-up back, zipper and hook-eye closure
    • Front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3389

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bringing The Heat Abstract Cutout Mini Dress

    You'll bring the sizzle to every party in this sexy abstract mini dress! The halter neckline with hoop insert adds a trendy touch while the cutout front and bodycon fit make a statement.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Halter neckline with tie straps, hoop insert
    • Front cutout
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000307

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: M, L

  • Flawless Floral Kimono Tie-Front Satin Crop Top

    You can't go wrong stepping out in this floral satin kimono tie-front top on a getaway or having a sunset dinner! Show off your fashion sense with this crop top with stunning three-quarter length kimono sleeves, tie-front detail, and a dainty floral print. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Flawless Floral High Rise Wide-Leg Satin Pants

    Fit & Features

    • Dainty floral print, satin fabric, no stretch
    • Tie-front
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06204-1751

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Button Up Darling Mid-Rise Denim Shorts

    Upgrade your summer wardrobe with these denim shorts for a darling look all season! These stylish shorts feature a flattering mid-rise waist and unique button trim pockets for added flair.

    Fit & Features

    • Dark wash denim fabric
    • Mid-rise waist
    • Button trim front pockets, belt loops
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-000054

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: M, L, XL

    Product Badge:
    • Sale
  • Gorgeous Allure Ruched Chiffon Bra Top

    Radiate your gorgeous allure in this sultry ruched chiffon bra top! Designed with an airy sheer chiffon fabric with a front knit lining for coverage, this bra top is perfect for looking sunkissed this season. It features a sleeveless subtle sweetheart neckline, ruching at the bust with padding for support, and adjustable spaghetti straps for a customized fit. The smocked back design offers added stretch, while the ultra-cropped fitted hem creates a snatched silhouette. Complete the look with the matching palazzo pants!

    Shop Matching Bottoms: Gorgeous Allure Chiffon Palazzo Pants

    Fit & Features

    • Sheer chiffon fabric, front knit lining
    • Sweetheart neckline
    • Ruched bust, padding
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Ultra-cropped hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2537

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Mode Espadrille Platform Wedge Heels

    Capture the effortlessly chic vibe of the summer season with these espadrille platform wedge heels! They feature an open almond-shaped toe with a wide toe strap, a thin adjustable ankle strap with a buckle closure, a closed back with a woven design, and a tall platform wedge heel for a beachy boho look. Style with a pearl necklace and hoop earrings.

    Fit & Features

    • 5" Platform wedge heel
    • Espadrille material
    • Open almond toe, wide toe strap
    • Thin adjustable ankle strap with buckle
    • Closed back with woven design
    • Faux leather luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07406-0347

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek And Sultry Tie Front Crop Top

    Sleek and sultry, this tie front crop top makes the perfect instant outfit with the matching skirt! 

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • V-neckline
    • Tie front
    • Cropped hem
    • Runs true to size

     

    Shop The Matching Skirt: Sleek And Sultry Bodycon Ruffle Mini Skirt

    Style Number/Barcode: 06202-000031

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: OFF, WHITE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Sunny Vibes Woven Wide-Leg Pants

    These airy woven wide-leg pants will bring the sunny vibes to your weekend plans! Designed with a lightweight woven fabric, they feature a flattering high-rise elasticized waist, front pockets, and a flowy wide-leg silhouette. Style with the matching crop top for a fabulous 'fit!

    Shop Matching Top: Sunny Vibes Bow Back Woven Crop Top

    Fit & Features

    • Woven fabric with minimal stretch
    • High-rise elasticized waistband
    • Wide-leg fit
    • Dual front pockets
    • Runs true to size

    Style Number/Barcode: 06402-1365

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cascading Romance Ruffle Floral Skater Dress

    Get swept away into a world of romance in this floral skater dress perfect for a shower or date! The square neckline and tie-shoulder spaghetti straps add a touch of sweetness, while the stretchy smocked bodice ensures a comfortable fit. The skater silhouette and tiered ruffled hem make this dress perfect for twirling the night away. Complete the look with earrings.

    Fit & Features

    • Floral print, chiffon fabric with woven skirt lining
    • Square neckline
    • Tie-shoulder spaghetti straps
    • Stretchy smocked bodice
    • Skater silhouette with ruffles
    • Runs true to size

    Style Number/Barcode: 05101-2994

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Adorable Allure Puff Sleeve Tie-Back Crop Top

    Showcase an adorable allure in the cutest puff sleeve crop top for casual summer parties! Designed with a stretchy knit fabric, it features a plunging V-neckline and short puff sleeves with elastic cinched hems. The trendy open back is accented with scrunched cross-back straps and lower tie-back straps for a customized fit, leading to a fitted cropped hem. Style with high-rise jeans and sneakers.

    Fit & Features

    • Stretchy double-lined knit fabric
    • Plunge V-neckline
    • Short puff sleeves
    • Open back, cross-back straps, lower tie-back straps
    • Fitted elasticized cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5186

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Breeze Strapless Wide-Leg Jumpsuit

    Feel the breeze in this cute tropical jumpsuit while on vacation! It showcases a sleek strapless neckline and flattering wide-leg silhouette perfect for layering over a swimsuit.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Strapless neckline
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-000002

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

  • Country Babe Colored Stone Straw Cowboy Hat

    A distressed cowboy hat featuring trendy colored stones along a string tie, perforated design, and a wide brim to help shade from the sun. Perfect for styling with cowboy boots.

    Fit & Features

    • Colored stones along the string tie
    • Perforated design
    • Wide brim
    • Adjustable inner strings
    • Distressed straw material

    Style Number/Barcode: 07302-1641

    Category Name: Vacation Looks

    Price: $12.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Splashin' Around Eyelet Ruffle Swim Shorts

    Splish-splash-looking flirty in these eyelet ruffle swim shorts perfect for pool parties, beach days, and vacations!

    Fit & Features

    • Eyelet fabric
    • High-rise elasticized waist
    • Ruffle trim
    • Runs true to size

    Style Number/Barcode: 07105-000001

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Here To Play Halter Skater Romper

    Perfect for day or night play, this cute romper combines comfort with head-turning appeal. This flirty, figure-flattering piece features a daring plunge neckline and playful skater silhouette that moves with you.

    Fit & Features

    • Smooth knit, stretchy fabric
    • Plunge halter neckline, tie closure
    • Flowy skater silhouette
    • Short hem
    • Runs true to size

    Style Number/Barcode: 06503-000060

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: S, M, L

  • Sunny Daze Straw Crossbody Bag

    Embrace sunnier days in this summer-ready straw crossbody bag featuring an adjustable chain-link strap, a top flap with snap closure, and a spacious lined interior with a single pocket. Complete the look in a cute bikini set for strolling the beaches.

    Fit & Features

    • Adjustable chain-link strap
    • Straw material 
    • Top flap with snap closure
    • Spacious lined interior with a pocket

    Style Number/Barcode: 07203-1069

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Vibe Cutout Strappy Slide Sandals

    The perfect cutout strappy slide sandal for sun-soaked days! 

    Fit & Features

    • Round toe
    • Strappy cutout design
    • Adjustable strap
    • Flat sole
    • Slide on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1276

    Category Name: Vacation Looks

    Price: $25.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: 7.5

  • Leafy Greens Charm Hoop Earrings

    Eat your greens. Dress up your look in these dangle leaf charm earrings featuring a large sleek hoop and a fish hook with a rubber-back stopper for a secure fit. Style with a boho-inspired dress for the music festival season!

    Fit & Features

    • Dangling leaf charms
    • Large sleek hoop
    • Fishhook, rubber-back stopper

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-1281

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Out Of Office Gradient Oversized Sunglasses

    These sunnies say “catch me on a yacht”—even if it’s just brunch. With oversized gradient lenses and glam hardware, these sunglasses are made for low-effort luxe and spontaneous selfies.

    Fit & Features

    • Rimless square-shaped oversized design
    • Metal chain-link detail on the arms
    • Flexible nose pads
    • Gradient-tinted lenses

    Style Number/Barcode: 07008-000058

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

  • Summer Muse Linen Thong Wedges

    These chic linen thong wedges will radiate bold summer vibes! Designed with a woven linen material, these heels are perfect for your getaway vacays. They feature a tall wedge heel for comfortable wear, a trendy square-shaped toe, a criss-cross thong strap design, and an open back for easy on-and-off styling. Pair with a flowy maxi dress and your fave shades.

    Fit & Features

    • 4.5" Wedge heel
    • Open square toe
    • Criss-cross thong strap design
    • Open back
    • Linen material, faux leather insole
    • Runs true to size

    Style Number/Barcode: 07406-0345

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale