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.

  • Under The Sun Long Sleeve Tie-Front Crop Top

    A crochet crop top perfect for fun under the sun! The top boasts trendy flare long sleeves and a tie-front design that flaunts your figure.

    Fit & Features

    • Crochet knit fabric
    • Flare long sleeves
    • Tie-front design
    • Ultra cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-000081

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Flutter Some Hearts Butterfly Charm Earrings

    You'll def flutter some hearts in these adorable butterfly charm earrings! Featuring a cascading drop design with rhinestone embellishments, these earrings couldn't get any more whimsical. Pair with a flirty skater dress and some sleek stilettos for your next party.

    Fit & Features

    • Linear dainty drop design
    • Rhinestone embellished butterfly charm
    • Post back closures



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

     

    Style Number/Barcode: 07001-0435

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wanderlust Mode Cutout Tube Top

    Shop Matching Pants: Wanderlust Mode Wide-Leg Pants

    Fit & Features

    • Smooth knit fabrication, double-lined 
    • Sleeveless square neckline
    • Cutout design from bust through hem
    • Beaded accents
    • Mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000188

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: BURGUNDY, RUST

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Fashionable Good Time Espadrille Flat Sandals

    Make sure to pack these espadrille flat sandals to ensure you have a fashionable good time on your next getaway! Featuring a closed round toe and adjustable ankle strap, these sandals offer a comfortable fit. The flat sole and cushioned faux leather insole make these shoes perfect for all-day wear. Complete the look with a trendy crossbody bag.

    Fit & Features

    • Closed round toe
    • Adjustable ankle strap, buckle closure
    • Flat sole
    • Faux leather cushioned insole
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07405-0076

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Infinite Possibilities Tie Front Crop Top

    Take the stress out of styling an outfit with this breezy crop top! Designed from a woven fabric, this top features adorable ruffled short sleeves and a flirty tie-front design that flaunts your figure along with the cropped hem. Complete the look with denim shorts and cute sandals!

    Fit & Features

    • Airy woven fabric, no stretch
    • Ruffled short sleeves
    • Tie-front closure
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06204-1853

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Muse Floral Print Maxi Skirt

    Serve fab vibes on vacay in this maxi skirt featuring a bold floral print pattern. Style with the matching tube top for an iconic 'fit.

    Shop Matching Top: Bold Muse Floral Print Tube Top

    Fit & Features

    • Smooth knit fabric, high stretch
    • Large floral print
    • Mid-rise waist
    • Hip-hugging fit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000047

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: M, L

    Product Badge:
    • Part of a Set
  • Living My Best Life Satin Tie-Dye Tube Top

    Ideal for sunny days, living your best life. This satin tie-dye tube top elevates your look with a sleek strapless neckline and pointed crop hem that flaunts your figure.

    Fit & Features

    • Tie-dye print, satin fabric, stretchy smocked back
    • Strapless tube neckline
    • Pointed crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000042

    Category Name: Vacation Looks

    Price: $26.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Day Dream High-Rise Wide Leg Pants

    Look like a tropical day dream in these high-rise pants while on vacation! The elasticized waistband ensures a comfortable fit, while the wide-leg silhouette and vibrant tropical print add a touch of paradise to your outfit. Complete the look with the matching top and skirt.

    Shop Matching Top: Tropical Day Dream Tie-Front Crop Top
    Shop Matching Skirt: Tropical Day Dream High-Rise Wrap Mini Skirt

    Fit & Features

    • Tropical print, stretchy knit fabric
    • High-rise elasticized waistband
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2469

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Home Lace-Up Gingham Corset Top

    Perfect for a day out, this sweet gingham corset top is designed to charm! With a lace-up back and gingham pattern, this top will give you a flattering silhouette while adding a touch of vintage flair to any outfit.

    Fit & Features

    • Gingham print, woven fabric, no stretch
    • Square neckline
    • Adjustable spaghetti straps, halter tie strap
    • Flexible boning
    • Bungee cord lace-up back, smocked panel
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000019

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic High-Rise Destructed Cut-Off Denim Shorts

    Create the cutest summer 'fits with this classic pair of destructed cut-off denim shorts! Detailed with trendy distressed detailing on the medium-wash denim fabric, these jean shorts are the perfect casual staple. They feature a flattering high-rise waist, a fitted cut-off hem, a traditional five-pocket and belt loop design, and a secure front button and hidden zipper closure. Style with a crop top and strappy sandals.

    Fit & Features

    • Distressed denim fabric, moderate stretch
    • High waist
    • Fitted cut-off hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Runs true to size

    Style Number/Barcode: 06603-0389

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Flutter Sleeve Tie-Front Eyelet Crop Top

    Capture hearts with this flirty flutter sleeve tie-front crop top! Designed with a lightweight woven fabric, it features a ruffled V-neckline with short flutter sleeves, a tie-front design for a stylishly cinched silhouette, a partial low back, and a cropped hem with an adorable eyelet trim. Complete the look with denim shorts and sandals.

    Fit & Features

    • Textured woven fabric, sewn-in knit lining
    • Ruffled V-neckline
    • Short flutter sleeves
    • Tie-front cinched silhouette
    • Partial low back
    • Cropped hem with eyelet trim
    • Runs true to size

    Style Number/Barcode: 06003-2581

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Sun Lace Ruffle Mini Dress

    Sway to the beat of your fave artist in this lace ruffle mini dress boasting a form-hugging fit and shark bite hem that pairs perfectly with boots!

    Fit & Features

    • Lace lined fabric
    • Square neckline, bust tie
    • Wide shoulder straps
    • Form-hugging fit
    • Shark bite ruffle mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4006

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY, BLACK

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

  • Exotic Vibes Strapless Tie-Front Tropical Romper

    You'll be looking exotic and beautiful in this tropical romper on vacation or by the pool! Featuring a flattering strapless sweetheart neckline and tie-front bust, this romper also offers a comfortable and stylish fit with its stretchy smocked back with cutout and a flowy short-length hem. Complete the look with a layered necklace and strappy sandals.

    Fit & Features

    • Tropical print, woven fabric lined with stretchy knit
    • Strapless sweetheart neckline
    • Tie-front bust
    • Smocked back with cutout
    • Flowy short-length hem
    • Runs true to size

    Style Number/Barcode: 06403-0427

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Talker Strappy Back Halter Skater Mini Dress

    Sweeten any room with your vibe in this halter skater dress, which flaunts a strappy open back that turns heads with every wear! 

    Fit & Features

    • Woven fabric, stretchy knit lining
    • Halter V-neckline with spaghetti strap tie
    • Open back with tie-back detail
    • Skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6029

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sway With The Palm Print Mesh Duster

    Sway with the breeze in this palm print mesh duster to layer over your chic vacation or pool party look! The duster has fitted long sleeves and an open front design giving everyone a peek at your cute self, and a flowy longline hem. Complete the look in flat sandals and sunnies!

    Fit & Features

    • Palm print
    • Stretchy sheer mesh fabric
    • Long fitted sleeves
    • Flowy longline hem
    • Runs true to size

    Style Number/Barcode: 06202-0445

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sky Gazing Moon Star Chain Belt

    Adorn yourself with celestial style with this moon star chain belt perfect for skygazers and dreamers! Featuring charming moon and star charms and a secure lobster clasp closure, this chain belt adds a touch of magic to any outfit. Complete the look in a trendy denim romper for a festival, concert, or night at the fair!

    Fit & Features

    • Moon and star charms
    • Chain belt
    • Lobster clasp closure

    Style Number/Barcode: 07301-1109

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Safari Babe Zebra Rhinestone Faux Suede Cowboy Hat

    Look and feel like a total safari babe in this zebra cowboy hat! This hat is made from soft faux suede and features a curved wide brim to help protect from the sun and an inner adjustable string for a snug fit. The rhinestone embellished trim and cord with adjustable toggle add a touch of glamorous detail. Complete the look in a flirty romper and boots for a jungle adventure!

    Fit & Features

    • Zebra print
    • Curved wide brim
    • Rhinestone embellished trim and cord with adjustable toggle
    • Inner adjustable strings
    • Faux suede material

    Style Number/Barcode: 07302-1638

    Category Name: Vacation Looks

    Price: $4.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Want To Want Me Floral Crochet Tie Front Top

    Wrap yourself in the bohemian charm of this floral crochet top! With kimono half sleeves and a tie-front design, this top is perfect for adding a touch of boho vibes to any outfit.

    Fit & Features

    • Sheer floral crochet knit fabric
    • Kimono half sleeves
    • Tie-front
    • Crop hem
    • Runs true to size

    Style Number/Barcode: 06204-000010

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Playfully Perfect High Rise Slit Mini Denim Skirt

    This mini denim skirt is playfully perfect for every casual social plan on your radar! With a high-rise waist and curve-enhancing seams along the bodycon silhouette, this skirt flatters your figure. Plus, the dual front slits add a flirty touch while the mini-length hem keeps things playful. Complete the look in a cute tee and sneakers.

    Fit & Features

    • Medium-wash denim fabric, no stretch
    • High-rise waist
    • Bodycon silhouette
    • Five-pocket styling, front button closure
    • Hidden zipper closure
    • Runs true to size

    Style Number/Barcode: 06601-0197

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Under The Sun Tropical Flower Hair Comb

    Enjoy the island under the sun adorning your tresses with this beautiful tropical flower hair comb! Complete the look in a matching set and sandals.

    Fit & Features

    • Tropical flower hair comb

    Style Number/Barcode: 07006-0469

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fun Favorite High Rise Distressed Denim Shorts

    Grab your bestie and throw on these denim shorts for a fun summer adventure! Made from a medium wash fabric with a cool vintage-inspired color fading, these jean shorts will be essential all season. They feature a flattering high-rise waist, distressed accents for a major trend factor, and an edgy cut-off hem. Complete the look in a cute crop top and sandals!

    Fit & Features

    • Medium wash denim, color fading effect
    • High rise waist
    • Distressed accents, cut off hem
    • Front button and hidden zipper closure
    • Five-pocket styling
    • Runs true to size

    Style Number/Barcode: 06603-0395

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Mode High-Rise Cotton Shorts

    Activate summer mode with these lightweight cotton shorts featuring a high-rise elasticized waist, dual front pockets, and a fitted silhouette. Style with the matching bra top and button-down top for an effortlessly chic look.

    Shop Matching Set: Summer Mode Cotton Bra Top, Summer Mode Button-Down Cotton Top

    Fit & Features

    • Textured cotton fabric, no stretch
    • High-rise elasticized waist
    • Dual front pockets
    • Fitted silhouette
    • Shorts in size small have a 9" front rise with a 1.5" inseam
    • Runs true to size

    Style Number/Barcode: 06303-000030

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: CHARTREUSE

    Available Size: S, M, L

    Product Badge:
    • Part of a Set
  • Sweet Flirt Flutter-Sleeve Ditsy Floral Tie-Front Top

    Sweet and flirty, this flutter-sleeve floral tie-front top will capture the soft girl trend! The lightweight knit fabric is detailed with an adorable ditsy floral print for the cutest vibes. The top features a V-neckline with a tie-front design, short flutter sleeves for a feminine touch, and a cropped hem with a relaxed fit. Style with the matching mini skirt for a day date!

    Shop Matching Bottoms: Sweet Flirt High Waist Ditsy Floral Ruched Mini Skirt

    Fit & Features

    • Ditsy floral printed knit fabric, moderate stretch
    • V-neckline with tie-front design
    • Short flutter sleeves
    • Cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06202-0464

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breezy Look Ruffled Cutout Woven Maxi Dress

    Create a breezy-chic look with this woven maxi dress that will prove to be a summer staple! Designed with a lightweight woven fabric accented with ruffled trims, the long dress features a sleeveless square neckline with a keyhole cutout and tie-front detail, adjustable spaghetti straps for a customized fit, and dual cutouts at the stretchy smocked waist that lead to an open lower back. The tiered flowy A-line silhouette will give you an effortlessly pretty look. Style with strappy sandals.

    Fit & Features

    • Woven fabric, ruffled trims, short knit stretchy lining
    • Square neckline, keyhole cutout with tie-front
    • Adjustable spaghetti straps
    • Stretchy smocked waist
    • Dual cutouts leading to open lower back
    • Tiered flowy A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5729

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free