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.

  • Boho Dreams Printed Cross Waist Flare Pants

    Daydream in these boho-printed pants perfect for festivals, concerts, and backyard parties! They feature a flattering cross-high waist, a hip-hugging fit, and a flared hem on stretchy brushed knit fabric. Complete the look in a lace-up crop top.

    Fit & Features

    • Cross high waist
    • Hip-hugging fit
    • Flared hem
    • Boho print
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06502-2318

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Fun Pleated Micro Mini Skirt

    Create trendy fits' with this micro mini skirt for tons of fun under the sun! It features a wide low-rise frayed waist, front pleating, and a frayed mini-length hem on twill denim fabric with a slight stretch. Complete the look in a cute graphic tee and platform sandals!

    Fit & Features

    • Low-rise wide frayed waist
    • Front pleating
    • Frayed mini-length hem
    • Dual front buttons and hidden zipper closure
    • Belt loop accents, two pocket styling
    • Twill denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06301-0154

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Adventure Twill Cargo Joggers

    Adventure in style around town in these twill cargo joggers perfect for giving your closet a streetwear vibe! They feature a high-rise elasticized drawstring waist, side pockets, a loose-fit leg silhouette, and lower-side flap pockets, elasticized hem, and are crafted from a woven on-stretch fabric with a cool washed effect. Complete the look with a basic tank top and sneakers.

    Fit & Features

    • High-rise elasticized drawstring waist
    • Side pockets, lower side flap pockets
    • Loose-fit leg silhouette
    • Elasticized hem
    • Woven twill fabric, washed effect, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0758

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Luxe Rhinestone Espadrille Wedges

    Take luxurious steps on vacation in these glitzy espadrille wedges featuring an almond toe, wide rhinestone straps, a platform sole, and a slingback ankle strap with buckle closure. Style with a chic crossbody purse to complete the look!

    Fit & Features

    • Almond toe
    • Wide rhinestone straps
    • Platform sole
    • Slingback ankle strap, buckle closure
    • Espadrille trim
    • Runs true to size

    Style Number/Barcode: 07406-0331

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Real Style Faux Leather Platform Heels

    These faux leather heels have got real style! They feature a square toe, wide toe strap, a thin block heel, a platform, an ankle strap with buckle closure, and a slightly cushioned insole. Complete the look with a trendy crossbody bag for a daytime soiree!

    Fit & Features

    • Square toe, wide toe strap
    • Thin block heel, platform
    • Ankle strap with buckle closure
    • Slightly cushioned insole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07401-4406

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Away This Weekend Buckle Platform Wedges

    These platform wedges are ready for your weekend away! They feature a square toe, a faux leather strap with studs and a buckle detail, a wooden-like sole, and a wrap-style ankle strap with a buckle closure and stud accents. Complete the look in a wide-leg jumpsuit for a dinner with a view!

    Fit & Features

    • Square toe
    • Faux leather strap, studs, buckle detail
    • Wooden-like platform sole
    • Wrap-style ankle strap, buckle closure
    • Runs true to size

    Style Number/Barcode: 07406-0335

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Looks Mesh V-Neck Babydoll Dress

    Showcase a dreamy look in this mesh babydoll dress perfect for date nights or parties! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched bust seams, and a flattering babydoll style silhouette with a mini-length hem. Complete the look in sleek hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Ruched bust seams
    • Babydoll style silhouette
    • Mini-length hem
    • Airy mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4971

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paint Me In Floral V-Neck Maxi Dress

    This floral maxi dress will fit like a dream and give off major artsy vibes! It features a sleeveless V-neckline, spaghetti straps, a hip-hugging fit, and a sultry front slit along the flowy hem. Complete the look in dainty earrings for a daytime soiree!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Hip-hugging fit
    • Front slit, flowy maxi-length hem
    • Floral watercolor print
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5018

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay In Bali One-Shoulder Maxi Dress

    Vacation in sultry style wearing this maxi dress! Serve major looks on the island in this dress featuring a sleeveless one-shoulder neckline, a tank strap with a hoop insert, and a form-hugging slim silhouette with a high side slit and ruched seam on textured knit fabric. Complete the look in chic sandals.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Tank strap, hoop insert
    • Form-hugging, slim silhouette
    • High side slit, side ruched seam
    • Maxi-length hem
    • Textured knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4970

    Category Name: Vacation Looks

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Modern Marvel One-Shoulder Mini Dress

    Strut looking like a modern work of art in this marble-printed mini dress all over town! It features a sleeveless one-shoulder neck, an adjustable spaghetti strap, a side adjustable ruched string, and a bodycon silhouette. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless one-shoulder neck
    • Adjustable spaghetti straps
    • Side ruched string
    • Bodycon silhouette
    • Mini-length hem
    • Marble-printed mesh fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4989

    Category Name: Vacation Looks

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What A Sight Eyelet Lace Lace-Up Dress

    You'll be quite a dreamy sight in this eyelet lace skater dress! Perfect for wedding showers, grabbing lunch with the girls, or backyard parties. It features adorable puff short sleeves, a sweetheart neck with an underbust seam, an open lace-up back, and a flattering short-length silhouette. Complete the look in strappy block heels.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, underbust seam
    • Open lace-up back
    • Skater silhouette
    • Short-length hem
    • Eyelet lace cotton fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4946

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Intentions Floral Tube Top

    Show off your sweet side in this adorable tube top! It features a sweetheart neckline with a ruched bust, halter spaghetti straps, a smocked back panel, and a majorly cropped hem. The woven fabric features an all-over ditsy floral print pattern. Style with the matching skater skirt for a brunch-ready look.

    Shop Matching Bottoms: Sweet Intentions Floral Skater Skirt

    Fit & Features

    • Sleeveless sweetheart neckline, ruched bust
    • Halter spaghetti straps, tie at the back of the neck
    • Smocked back panel
    • Cropped fit
    • Ditsy floral print
    • Woven fabric, front knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1833

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Intentions Floral Skater Skirt

    Show off your sweet side in this adorable skater skirt! It features a high-rise smocked waist with an adjustable drawstring, pleated detailing, and a short, fit and flare silhouette. The woven fabric features an all-over ditsy floral print pattern. Style with the matching tube top for a brunch-ready look.

    Shop Matching Top: Sweet Intentions Floral Tube Top

    Fit & Features

    • High-rise smocked waist, elastic waistband
    • Adjustable drawstring
    • Pleated detailing
    • Short hem, fit and flare silhouette
    • Ditsy floral print
    • Woven fabric, full knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06301-0133

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Island Guru Pleated Bandeau Top

    Elevate your island vacation look with this sassy bandeau crop top perfect for dinner and drinks! It features a sleeveless halter neckline with tie closure and is composed of a pleated satin fabric with lining. Style with the matching bottoms.

    Shop Matching Bottoms: Island Guru Pleated Wide Leg Pants

    Fit & Features

    • Sleeveless halter neckline, tie closure
    • Cropped hem
    • Pleated satin fabric with lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06003-2135

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Guru Pleated Wide Leg Pants

    Elevate your island vacation look with these sassy satin pants perfect for dinner and drinks! It features a flattering high-rise elasticized smocked waist, and a wide-leg silhouette and is composed of pleated satin fabric with lining. Style with the matching top.

    Shop Matching Top: Island Guru Pleated Bandeau Top

    Fit & Features

    • High-rise elasticized smocked waist
    • Wide-leg silhouette
    • Pleated satin fabric with lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06402-0621

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Running Wild Zebra Print Mini Skirt

    Look stylish in this zebra print mini skirt running wild keeping up with your social calendar! It features a high-rise elasticized waist, a bodycon silhouette, and a flirty slit hem on brushed knit stretchy fabric. Complete the look with the matching top.

    Shop The Matching Top: Running Wild Zebra Print Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Bodycon silhouette
    • Slit mini-length hem
    • Zebra print
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06501-0787

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Running Wild Zebra Print Crop Top

    Look stylish in this zebra print mini skirt running wild keeping up with your social calendar! It features a sleeveless halter neckline, spaghetti straps, an open lace-up back, and a fitted crop hem on brushed knit stretchy fabric. Complete the look with matching bottoms.

    Shop The Matching Bottoms: Running Wild Zebra Print Mini Skirt

    Fit & Features

    • Sleeveless halter neckline
    • Spaghetti straps, lace-up open back
    • Fitted crop hem
    • Zebra print
    • Brushed knit stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06001-4696

    Category Name: Vacation Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picnic Date Ditsy Floral Chiffon Romper

    This adorable ditsy floral chiffon romper will have you picture-perfect for a picnic date! It features a sleeveless V-neckline, adjustable spaghetti straps, a high waist with a sheer floral crochet trim, flowy shorts, and a fit and flare silhouette. The airy chiffon fabric features a dainty ditsy floral print pattern. Complete the look with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, back zipper closure
    • High waist, sheer floral crochet trim
    • Flowy shorts, fit and flare silhouette
    • Ditsy floral print
    • Sheer chiffon fabric, lining
    • Runs true to size

    Style Number/Barcode: 06403-0252

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denim Daze Button Crop Vest

    The perfect denim vest to give our outfit a cute western vibe! It features a sleeveless V-neck, button-down front, faux pockets, and a curved crop hem. Style with best-selling bottoms for a festival or an art walk downtown!

    Fit & Features

    • Sleeveless V-neck
    • Button-down front
    • Faux pockets
    • Curved, crop hem
    • Non-stretch rifid denim fabric
    • Runs true to size

    Style Number/Barcode: 06203-0491

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feel The Rhythm Crochet Lace-Up Vest

    Feel the rhythm in this crochet vest perfect for festivals or concerts! It features a sleeveless V-neckline, wide shoulder straps, a front lace-up design, and a pointed crop hem. Complete the look in trendy denim shorts.

    Fit & Features

    • Sleeveless V-neckline
    • Wide shoulder straps
    • Front lace-up design
    • Pointed crop hem
    • Crochet fabric, sewn-in knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4803

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Meet In The Hamptons Linen Crop Top

    This linen crop top has a Hampton's getaway written all over it! Look cute strolling through the town in this top featuring a sleeveless halter V-neckline and dual tie-back neck and lower back straps. Style with the matching bottoms and a dainty necklace to complete the chic look!

    Shop Matching Bottoms: Meet In The Hamptons Linen Wide Leg Pants

    Fit & Features

    • Sleeveless halter V-neckline
    • Dual tie-back neck and lower back straps
    • Cropped hem
    • Lined linen fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2163

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Blooms Floral Mini Skirt

    Create an artsy-chic look with this floral mini skirt for an evening downtown! It features a high-rise waist, a front ruched seam atop a slit hem, and a bodycon silhouette on stretchy mesh-lined fabric. Style with a crop top and heels.

    Fit & Features

    • High-rise waist
    • Front ruched seam
    • Bodycon silhouette
    • Mini-length hem with slit
    • Floral artsy bloom print
    • Mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0802

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Look Your Cutest Floral Chiffon Mini Skirt

    Look your cutest in this floral mini skirt for a stylish stroll downtown to brunch! It features a high-rise waist, a form-hugging fit, and an asymmetrical ruffle trim on airy chiffon fabric. Complete the look in a basic strapless top and heels.

    Fit & Features

    • High-rise waist
    • Hidden side zipper and hook-eye closure
    • Form-hugging fit
    • Asymmetrical ruffle trim, mini-length hem
    • Ditsy floral print
    • Airy chiffon woven fabric
    • Runs true to size

    Style Number/Barcode: 06401-0490

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Miami Nights Ruched Mini Skirt

    Bring the heat and take on the night scene in this alluring mini skirt! It features a high-rise elasticized waist, ruched detailing down the side and back seams, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric offers plenty of stretch. Style with the matching crop top and a pair of strappy stilettos.

    Shop Matching Top: Miami Nights One-Shoulder Crop Top

    Fit & Features

    • High-rise elasticized waist
    • Ruched side and back seams
    • Mini-length hem
    • Form-hugging fit
    • Sheer mesh fabric, full knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0783

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale