Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

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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.

  • Style Quotient Platform Denim Block Heels

    Amp your style quotient in these sassy denim block heels perfect for any plans! The round toe and platform sole provide an elevated look, while the adjustable ankle strap with buckle closure secures the style. Complete the look in a mini dress and jacket.

    Fit & Features

    • 5" Block heel
    • Round toe
    • Platform sole
    • Contrast straps
    • Adjustable ankle strap, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4724

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Link Up Luxe Chain Necklace

    Bold neck, big flex. This chunky chain is your shortcut to instant cool-girl status. Layer it up or let it shine solo—it’s that versatile power piece every jewelry box needs.

    Fit & Features

    • High-shine metal with luxe finish
    • Chunky link chain silhouette
    • Lobster clasp closure for a secure fit

    Style Number/Barcode: 07002-000037

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Animal Instinct Leopard Oversized Sunglasses

    These trendy sunglasses feature oversized square frames with a fierce leopard pattern. Perfect for everyday styling.

    Fit & Features

    • Oversized square frame
    • Leopard pattern
    • 100% UV protection
    • Tinted lenses

    Style Number/Barcode: 07008-1109

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Living By The Sea Canvas Tote Bag

    Escape to the beach with this tote bag, featuring charming seashell and starfish prints that capture coastal beauty and a spacious interior perfect for any essentials.

    Fit & Features

    • Top handles
    • Seashell and starfish print design
    • Spacious interior
    • Canvas material

    Style Number/Barcode: 07203-000027

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Cowgirl Shell Trim Straw Cowboy Hat

    A straw cowboy hat perfect for a day at the beach or festival. This hat features a wide brim to help shade, a string trim with shell and stone decoration, and adjustable inner strings for a snug fit.

    Fit & Features

    • Straw material
    • Wide brim
    • String trim with shells and stone decoration
    • Adjustable inner strings

    Style Number/Barcode: 07302-1643

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kellie Strapless Ruffled Slit Lace Formal Dress

    Special Occasion

    A showstopping lace formal dress that exudes romance and modern elegance. Designed with a high strapless neckline, this long dress boasts a bodycon silhouette with flirty cascading ruffles and a sultry high-side slit. Complete the look with earrings and heels.

    Unapologetically bold, this dress is all about confidence. Keep the luxe look going with our stunning strapless prom dresses or discover the perfect fit among our stylish wedding guest dresses.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • High strapless neckline, non-slip grip lining
    • Side zipper and hook-eye closure
    • High-side slit
    • Bodycon silhouette
    • Long-length hem
    • Runs true to size

    Style Number/Barcode: 05002-8961

    Category Name: Vacation Looks

    Price: $64.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Born To Be Coveted Mid-Rise Lace-Up Denim Skort

    A coveted summer style starts with this mid-rise denim skort perfect for casual plans! Made from denim fabric, this skort is perfect for showing off your legs in a flirty mini-length hem. Its mid-rise waist and form-hugging fit will accentuate your curves, while the playful skirt overlay with lace-up detailing and a slit adds a touch of edginess. Complete the look in a flirty crop top and sneakers.

    Fit & Features

    • Denim medium wash fabric, no stretch
    • Mid-rise waist
    • Back zipper hook-eye closure
    • Lace-up, slit accent
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0379

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Golden Hour Seashell Sandals

    Vacay vibes in every step. These shell-accented sandals are your new go-to for beach walks, brunch looks, and everything in between—comfy, cute, and made for your golden hour moments.

    Fit & Features

    • Faux leather material
    • Open square-shaped toe
    • Thong strap design
    • Metal shell accent
    • Open back, on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-000020

    Category Name: Vacation Looks

    Price: $16.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Radiant Accent Floral Boho Satin Scarf

    The perfect satin scarf to give your outfit a radiant accent! The silky satin woven material is designed with a vibrant floral bohemian-inspired print for a trendy allure. Style this scarf as a pretty headwrap, around your neck, or tied on your bag as a chic accent! Complete the look with a sleek choker necklace.

    Fit & Features

    • Silky satin woven material
    • Floral bohemian print
    • Multiple ways to style and wear

    Style Number/Barcode: 07305-0495

    Category Name: Vacation Looks

    Price: $12.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: NS

  • City Of Love V-Neck Ruffle Babydoll Dress

    Grab your baguette, passport, and this babydoll dress cause the city of love is calling your name! The playful ruffled shoulder straps and convenient side pockets add a touch of whimsy to this flirty dress. The babydoll silhouette and ruffled tiered hem make it perfect to sweep through Paris looking adorable! Complete the look in strappy sandals and a purse.

    Fit & Features

    • Woven fabric
    • Ruffled shoulder straps
    • Side pockets
    • Babydoll silhouette
    • Ruffled tiered short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5423

    Category Name: Vacation Looks

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl On The Go Square Sunglasses

    Made for the girl on the go. These square-frame sunglasses bring effortless cool to every outfit, whether you're brunch-bound or dodging exes at the beach party.

    Fit & Features

    • Square frames
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000047

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Retro Mood Tortoiseshell Oval Sunglasses

    Lowkey iconic, highkey essential. These tortoiseshell oval sunglasses give your everyday 'fits that effortless vintage vibe—perfect for rooftop brunches, market strolls, or literally anytime you want to look cool.

    Fit & Features

    • Small oval-shaped design
    • Tortoiseshell plastic frame
    • Built-in nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000048

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Me Away Tube Midi Dress

    Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!

    Fit & Features

    • Texture knit cotton-blend fabric, moderate stretch
    • Sweetheart strapless tube neckline
    • Twist bust
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000018

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, S, M, L

  • Blooming Chic Flower Detail Faux Leather Block Heels

    Create a blooming chic 'fit perfect for the season with these cute block heels! Made with smooth faux leather, they feature an open square-shaped toe, a detailed toe strap with faux leather flower accents and faux pearl center beading, thin adjustable ankle and heel straps, and a sleek thin block heel. Style with the matching crossbody bag for an adorable look!

    Shop Matching Bag: Blooming Chic Flower Detail Clear Crossbody Bag

    Fit & Features

    • 3" Thin block heel
    • Faux leather upper
    • Open square toe
    • Toe strap, faux leather flower accents, faux pearl beading
    • Adjustable ankle and heel straps, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4702

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Poolside Paradise Floral Scrunch Bikini Bottoms

    So pretty and made for tanning, these floral bikini bottoms offer a flattering V-shaped low-rise waist and a scrunched thong back that flaunts your curves! Pair with the matching bikini top.

    Shop Matching Top: Poolside Paradise Floral Triangle Bikini Top

    Fit & Features

    • Floral print, stretchy knit fabric
    • V-shaped low-rise waist
    • Scrunched thong back coverage
    • Runs true to size
    • Returns are not accepted without the hygienic liner

    Style Number/Barcode: 07105-000010

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: L

    Product Badge:
    • Sale
  • Blissful View High Rise Crochet Midi Skirt

    Enjoy stylish bliss in this crochet midi skirt on your next getaway or weekend outing! The skirt offers a flattering high-rise elasticized waist, a bodycon silhouette, and a midi-length hem. Complete the look with the matching top.

    Shop Matching Top: Blissful View Halter Crochet Crop Top

    Fit & Features

    • Crochet fabric lined with knit
    • High-rise elasticized waist
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06501-1048

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Mode Ruched Bikini Top

    Activate sunny mode with this hot bikini top featuring a ruched bust, curved underwire for structure, and adjustable spaghetti straps. Style with the matching bikini bottoms to be sitting pretty poolside!

    Shop Matching Bottoms: Sunny Mode V-Cut Bikini Bottoms

    Fit & Features

    • Nylon-blend fabric, high stretch
    • Lined cups, curved underwire, no padding
    • Ruched bust
    • Adjustable spaghetti straps
    • Back strap with hook and bar closure
    • Runs true to size

    Style Number/Barcode: 07104-000005

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Exceptional Taste Large Hoop Earrings

    Your exceptional taste will show in these large hoop earrings that perfectly accessorize every outfit! Complete the look in a cocktail dress for a rehearsal dinner or dressy party.

    Fit & Features

    • Large hoops
    • Omega closure, rubber stopper

     

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

    Style Number/Barcode: 07001-2018

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Raise The Heat Floral Mesh Off-Shoulder Top

    Raise the heat with your bold allure in this floral mesh off-shoulder top! The asymmetric neckline and twisted straps add that trendy vibe to the fitted silhouette.

    Fit & Features

    • Mesh fabric, high stretch, sewn-in lining
    • Large floral print
    • Asymmetric off-shoulder neckline, twisted straps
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-000062

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: ORANGE

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Cutest Vibe Ruched Knit Tube Top

    Show off the cutest vibe in this trendy tube top with ruching down the sides for a flattering silhouette. Perf for styling with your fave pair of denim!

    Fit & Features

    • Cotton knit fabric, moderate stretch
    • Strapless straight neckline
    • Ruched side seams
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-000349

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: HEATHERGRAY, BROWN, DARK, DENIM, RED, WHITE, BLACK, OLIVE

    Available Size: XS, S, M, L

  • Sultry Style Halter Cutout Wide-Leg Jumpsuit

    Show off a sultry style on vacay or a weekend getaway in this cutout wide-leg jumpsuit! Designed with a stretchy smooth knit fabric with a full-length lining, it features a sleeveless plunging halter neckline, spaghetti straps with a tie-back design, and an alluring cutout bodice for a bold babe vibe. The fitted high waist leads to a hip-hugging fit and a trendy wide-leg silhouette. Complete the look with platform wedges.

    Fit & Features

    • Smooth knit fabric with knit lining, plenty of stretch
    • Plunging halter neckline with tie closure, partial open back
    • Cut out bodice
    • Hip-hugging fit
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2515

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chase The Sun Lace-Up Espadrille Wedges

    Flaunt a sunny day style in these lace-up espadrille wedges perfect for a beach day, backyard bbq, or vacation!

    Fit & Features

    • 4" wedge heel
    • Almond toe, curved band
    • Lace-up ankle straps
    • Platform wedge heel
    • Runs true to size

    Style Number/Barcode: 07406-0364

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: 7, 7.5, 8, 8.5, 9, 10

  • Unfazed Babe Oversized Square Sunglasses

    A pair of sunglasses featuring an oversized design, tortoise pattern, tinted lenses with 100% UV protection, and nose supports. Perfect for everyday wear.

    Fit & Features

    • Oversized design
    • Tortoise pattern
    • Tinted lenses
    • 100% UV protection
    • Nose supports

    Style Number/Barcode: 07008-1102

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serving Vibes Halter Crop Top

    This halter crop top will serve major stunning vibes for cocktails and dinner! It is designed with ruched side seams and a fitted crop hem that accentuates your figure.

    Fit & Features

    • Sheen knit fabric, sewn-in knit lining, high stretch
    • Halter plunge neckline with tie closure
    • Side ruched seams
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06001-000174

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: ORANGE, IVORY, MOCHA, WINE

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock