Vacation Dresses & Outfits

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STYLE SPOTLIGHT

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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.

  • Sassy Style Ruched Knit Halter Skater Dress

    Show off your sassy style at weekend outings in this adorable halter skater dress. Made with stretchy smooth knit fabric, it features a sleeveless V-neckline, trendy tie-back halter straps leading to a partially open back, ruched seams at the waist to accentuate your curves, a short double-layered skater skirt for a flirty vibe, and a fit-and-flare silhouette. Complete the look with a charm necklace and strappy mules!

    Fit & Features

    • Stretchy smooth knit, top knit lining
    • V-neckline, tie-back halter straps
    • Partially open back
    • Ruched seams at the waist
    • Double-layered skater skirt
    • Fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5832

    Category Name: Vacation Dresses & Outfits

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • 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 Dresses & Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Dresses & Outfits

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

  • 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 Dresses & Outfits

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Dresses & Outfits

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Dresses & Outfits

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Dresses & Outfits

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    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 Dresses & Outfits

    Price: $16.97 $39.90

    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 Dresses & Outfits

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pop Star Rhinestone High-Rise Denim Shorts

    Put on a show arriving in these rhinestone denim shorts! They feature a flattering high-rise waist, and stunning rhinestone swag chains across the front for a touch of glamour. The distressed accents add a trendy edge, while the fitted hem ensures a perfect fit. Complete the look in a bodysuit and boots for a concert or music festival!

    Fit & Features

    • High-rise waist
    • Rhinestone swag chains across the front
    • Distressed accents, fitted hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0364

    Category Name: Vacation Dresses & Outfits

    Price: $54.90

    Availability: In Stock

    Available Color: MED, DENIM

    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 Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Social Girlie High Rise Slit Midi Skirt

    Your social calendar is filling up and this midi skirt is here to help! Featuring a high-rise waist, side adjustable drawstring, and bodycon fit, this skirt will accentuate your curves and flatter your figure. The high-side asymmetrical slit adds a touch of intrigue while the midi-length hem keeps it chic. Complete the look in sandals.

    Fit & Features

    • Smooth knit stretchy fabric
    • High rise waist
    • Bodycon fit
    • Adjustable drawstring
    • Asymmetrical high side slit
    • Runs true to size

    Style Number/Barcode: 06501-1039

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ocean Breeze Cowl Neck Low Back Tropical Maxi Dress

    Relax poolside with a drink in hand and this tropical mesh maxi dress on! Featuring a playful cowl neckline, adjustable spaghetti straps, and a low back with criss-cross straps for a touch of intrigue. Its curve-hugging silhouette and maxi-length hem will make you feel like a tropical goddess on vacation! Complete the look in sunnies and sandals!

    Fit & Features

    • Tropical palm print, mesh fabric lined with stretchy knit
    • Cowl neckline
    • Adjustable spaghetti straps
    • Low back with criss-cross straps
    • Curve-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5645

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sway With Me Halter V-Neck Paisley Skater Dress

    Sway all day in this cute paisley skater dress perfect for summer parties and backyard BBQs! This dress features a halter V-neckline with spaghetti strap ties and a stretchy smocked bust for a flattering fit. The tie-back design adds a touch of playfulness, while the skater silhouette and ruffled hem will have you twirling all day! Complete the look in sandals and hoop earrings. 

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline with spaghetti strap ties
    • Stretchy smocked bust
    • Tie back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5575

    Category Name: Vacation Dresses & Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: NAVY, OLIVE, RUST

    Available Size: XS, S, M, L

  • Cute Sight Cateye Metal Sunglasses

    This pair of sunglasses features a cateye design on a sleek metal frame, tinted lenses with 100% UV protection, and rubber nose supports. Perfect for everyday styling.

    Fit & Features

    • Cateye design, sleek metal frame
    • Tinted lenses
    • 100% UV protection
    • Rubber nose supports

    Style Number/Barcode: 07008-1105

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blissful View Halter Crochet Crop Top

    Enjoy stylish bliss in this crochet top on your next getaway or weekend outing! The top offers a flattering halter neckline with a spaghetti strap tie and a fitted crop hem. Complete the look with the matching midi skirt.

    Shop Matching Bottoms: Blissful View Crochet Knit Midi Skirt

    Fit & Features

    • Crochet knit fabric, geometric pattern, knit lining
    • Halter neckline with spaghetti strap tie
    • Cropped length
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2271

    Category Name: Vacation Dresses & Outfits

    Price: $22.90

    Availability: In Stock

    Available Color: LIGHT, BLUE, NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Flirty Moves Ruffled Tie-Front Knit Crop Top

    Make major flirty moves and create an enticing aura in this ruffled tie-front crop top! Designed with a stretchy smooth knit fabric, it features a sultry V-neckline with a tie-front design, ruffled hems for that girly flair, spaghetti straps, and an asymmetric cropped hem. Style with the matching midi skirt for a girl's night out!

    Shop Matching Bottoms: Flirty Moves Ruffled Slit Knit Midi Skirt

    Fit & Features

    • Double-lined stretchy smooth knit fabric
    • V-neckline, tie-front design
    • Ruffled hems
    • Spaghetti straps
    • Asymmetric cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5451

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seamless Sculpt Bandeau Bra

    A bandeau bra designed to stretch with your body while offering a seamless and sculpting fit. This bra features a strapless neckline for no-fuss wear, removable padded bra cups that shape and support, and a seamless design on buttery smooth knit fabric. Style this bandeau with smooth shapewear shorts for a sleek silhouette.

    Fit & Features

    • Seamless, buttery smooth knit fabric
    • Strapless neckline
    • Removable padded bra cups
    • Runs true to size 

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07102-0327

    Category Name: Vacation Dresses & Outfits

    Price: $7.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

  • Pretty Style Beaded Stretch Bracelet Set

    Adorn your wrist with this pretty and stylish bracelet set! It features three stretchy bracelets with varying sleek beaded designs. Complete the look with trendy sandals for any occasion or plan!

    Fit & Features

    • Three stretchy bracelets
    • Varying beaded designs

    Style Number/Barcode: 07003-0572

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

  • Pretty Bold One-Shoulder Floral Mesh Crop Top

    Pretty and bold, this sleeveless crop top features a one-shoulder neckline, an adjustable side drawstring, and an asymmetrical-cut hem. The mesh fabric showcases a bold floral print.

    Fit & Features

    • Floral print, mesh fabric lined with mesh, stretchy
    • One-shoulder neckline
    • Adjustable side drawstring
    • Asymmetrical-cut cropped length hem
    • Runs true to size

    Style Number/Barcode: 06001-5482

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Match Sleeveless Striped Ribbed Knit Mini Dress

    You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

    Fit & Features

    • Striped pattern
    • Ribbed knit fabric with moderate stretch
    • Scoop neckline
    • Tank shoulder straps
    • Cutout back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1940

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Vacay High Rise Wide-Leg Trouser Pants

    Get ready for vacay packing these trouser pants for endless fun under the sun! Whether you're island hopping in Greece or sipping a mai tai on the beach, these pants will keep you so trendy. It boasts a flattering high-rise waist with side pockets for keeping your hands warm, a breeze wide-leg silhouette, plus a button front and hidden zipper closure to secure the style. Complete the look with the matching top.

    Shop Matching Top: Endless Vacay Strapless Tube Crop Top

    Fit & Features

    • Texture woven fabric
    • High-rise waist
    • Wide-leg silhouette
    • Side pockets
    • Front button and hidden zipper closure
    • Runs true to size

    Style Number/Barcode: 06402-1405

    Category Name: Vacation Dresses & Outfits

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress

    Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.

    Fit & Features

    • Polka dot print, satin fabric, no stretch
    • Butterfly lace trim sweetheart neckline
    • Button-down back and zipper hook-eye closures
    • Cutout back accent
    • Maxi length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3555

    Category Name: Vacation Dresses & Outfits

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale