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.

  • Charming Style Puff Sleeve Chiffon Skater Dress

    Create the sweetest charming style for your spring and summer parties in this chiffon skater dress! The airy sheer chiffon fabric offers that breezy lightweight feel and includes a stretchy knit lining for coverage. The short dress features a ruched square neckline, adorable short puff sleeves, dual high waist seams, and a fit-and-flare skater silhouette for a flirty vibe with a ruffled hem. Pair with sneakers for a cute and casual look!

    Fit & Features

    • Sheer chiffon fabric with stretchy knit lining
    • Ruched square neckline
    • Short puff sleeves with elasticized hems
    • High waist seams, back zipper with hook and eye closure
    • Skater silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3056

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheer Fun Off-The-Shoulder Crop Chiffon Blouse

    You'll have the most fun in this cute chiffon crop blouse on a date night or evening out! The breezy sheer peasant long sleeves and off-the-shoulder neckline add a flirty touch, while the adjustable front ruched drawstring allows for a personalized fit. Complete the look in a sleek faux leather midi skirt and pointy toe heels for a chic allure!

    Fit & Features

    • Chiffon woven fabric
    • Off-the-shoulder
    • Front ruched drawstring
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2355

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Eye-Catching Vibes Cut Out Bodycon Mini Dress

    Keep every eye on you in this bodycon mini dress for flawless vibes at parties! Made from a brushed soft knit double-lined fabric, this dress offers ultimate comfort and style. Featuring a square neckline, spaghetti straps, and a bodycon fit, this dress will enhance your curves and make you stand out. The side cut out and ruched seams add an edgy touch, while the mini-length hem flaunts your figure. Complete the look in sandals and earrings.

    Fit & Features

    • Brushed knit soft double-lined fabric, stretchy
    • Spagehtti straps
    • Side cut out, side ruched seams
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5640

    Category Name: Vacation Looks

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Baby Got Open Back Poplin Woven Mini Dress

    Get ready to turn heads in this open back poplin woven mini dress! This bodycon mini dress features a square neckline, spaghetti tie straps, and a spaghetti tie back strap for a playful twist along the sultry open back. Made with a lightweight poplin woven fabric, this dress is perfect for hot days and even hotter nights! Complete the look in heeled sandals and a purse.

    Fit & Features

    • Poplin woven fabric lined with stretchy knit
    • Spagehtti tie straps and back strap
    • Open back
    • Hidden side zipper and hook-eye closure
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5760

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Getaway Chic Marble Buckle Raffia Belt

    Define your silhouette in this chic raffia belt perfect for inspiring your next getaway! It features a marble print buckle closure and an adjustable fit on raffia material. Complete the look in clear stiletto mules.

    Fit & Features

    • Marble print buckle closure
    • Adjustable fit
    • Raffia material

    Style Number/Barcode: 07301-0857

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Chic Tiered Floppy Straw Hat

    Floppy and boho chic, this straw hat was made for fun under the sun! Pack this essential hat for vacations, weekend trips, or a beach day. It features a unique tiered design along the floppy brim that shades from the sun and adjustable interior strings so you can get a snug fit. Complete the look with the matching bag and heels!

    Shop Matching Shoulder Bag: Boho Chic Straw Shoulder Bag
    Shop Matching Tote Bag: Boho Chic Crossbody Straw Tote Bag
    Shop Matching Heels: Boho Chic Straw Platform Block Heels

    Fit & Features

    • Straw material
    • Tiered design
    • Floppy brim
    • Adjustable interior strings for a snug fit

    Style Number/Barcode: 07302-1555

    Category Name: Vacation Looks

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutest Style Halter Knit Crop Top

    You always have the cutest style, so this halter knit crop top is the perfect addition to your summer closet! The knit fabric adds a comfy cozy feel to the trendy silhouette. The top has a sleeveless high halter neckline and a front V-shaped hanky cropped hem. Pair with distressed jeans for your casual weekend plans!

    Fit & Features

    • Knit fabric, minimal stretch
    • Sleeveless high halter neckline
    • V-shaped hanky cropped hem
    • Fitted
    • Runs true to size

    Style Number/Barcode: 06005-1894

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Stunner Sleeveless Lace Trim Bodysuit

    Easily stun in this sleeveless bodysuit to layer under your favorite sheer blouses or layered with a cute jacket! The bodysuit is crafted from a double-lined rib knit stretchy fabric for comfort. It features a delicate lace trim square neckline, adjustable spaghetti straps for a perfect fit, a form-hugging fit that shows your shape, and a thong bottom with snap-button closures. Complete the look with a midi skirt, jacket, and heels for a date!

    Fit & Features

    • Double-lined rib knit stretchy fabric
    • Adjustable spaghetti straps
    • Lace trim
    • Form-hugging fit
    • Thong bottom, snap-button closures
    • Runs true to size

    Style Number/Barcode: 06002-1782

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lively Elegance Smocked Floral Babydoll Dress

    Indulge in elegance in this elegant floral babydoll dress perfect for wedding showers or graduations! With its stretchy smocked bodice and adjustable straps, you'll get a perfect fit. The chiffon fabric and vibrant floral print add a touch of elegance to the playful babydoll silhouette and ruffled short-length hem. Complete the look in sandals.

    Fit & Features

    • Floral print, chiffon fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Babydoll silhouette
    • Ruffled short-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5470

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Presence Strapless Slit Floral Maxi Dress

    Your presence will always be charming in this ditsy floral maxi dress at wedding showers, brunch, or casual parties! Adorned in a stunning disty floral print, this strapless dress features a ruffle trim neckline and padded bra cups for flattering support. The curve-hugging silhouette, front slit, and maxi-length hem create a captivating look, while the brushed knit stretchy fabric ensures comfort. Pair with earrings and strappy sandals.

    Fit & Features

    • Ditsy floral print
    • Brushed knit stretchy fabric
    • Padded bra cups
    • Front slit
    • Curve-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5541

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Vibes Braided Strap Platform Sandals

    These trendy braided strap platform sandals are perfect for sunset happy hours this season! They feature a cork block heel and platform sole, an open square-shaped toe, and multi-colored braided straps in a criss-cross design. The open back offers effortless on-and-off styling. Pair these sandals with gold hoops!

    Fit & Features

    • 4.5" Cork block heel, platform sole
    • Faux leather upper
    • Open square toe
    • Criss-cross multi-colored braided straps
    • Open back
    • On-and-off styling
    • Runs true to size

    Style Number/Barcode: 07401-4843

    Category Name: Vacation Looks

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Next Level Gladiator Flat Platform Sandals

    Take your style to the next level in these gladiator flat platform sandals perfect for spring to summer wear! Featuring an almond toe and a strappy caged design, these sandals are both chic and comfortable. The adjustable ankle strap with buckle closure ensures a perfect fit while the flat platform sole adds a touch of height to faux leather material. Complete the look in a trendy denim jacket.

    Fit & Features

    • Almond toe
    • Strappy caged design
    • Flat platform sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1171

    Category Name: Vacation Looks

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Glitzy Rhinestone Strappy Faux Leather Sandals

    Step out in glitzy style with these rhinestone strappy sandals! Made with faux leather material, they feature an open square toe, a wide twisted strappy design across the foot with rows of mini rhinestones, and a mini rhinestone outline on the flat sole for more sparkle. The open back offers effortless on-and-off styling. Pair these sandals with a fab handbag.

    Fit & Features

    • Faux leather upper
    • Square toe
    • Twisted strappy design with rhinestones
    • Rhinestone trim
    • Open back, flat sole, faux leather padded insole
    • On-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1181

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bloom With A View High Rise Floral Mini Skirt

    Take in your beauty in this floral mini skirt on vacation! Designed with a stretchy sheer mesh fabric with a lining, the delicate floral bloom print will bring out a touch of chic to any outfit. Featuring a high-rise elasticized waist, flattering side ruching to accentuate your curves on the bodycon fit, and a mini-length hem, this skirt is perfect for any getaway. Complete the look with the matching crop top!

    Shop Matching Top: Bloom With A View V-Neck Floral Crop Top

    Fit & Features

    • Stretchy sheer mesh fabric, sewn-in knit lining
    • Floral bloom print
    • High-rise elasticized waist
    • Bodycon fit
    • Ruched side seams
    • Runs true to size

    Style Number/Barcode: 06501-0965

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing Rainbows Press On Nail Kit

    Color your everyday style in this rainbow press-on nail kit including everything you need to achieve a fun look. The exclusive kit offers two sets of colorful press-on nails with artsy designs, one mini nail file, a prep pad, and glue. Follow the easy instructions on the prep pad for the best results. Complete the look in sandals for a daytime brunch or party!

    Fit & Features

    • Press on nail kit
    • Two sets of colorful press-on nails, artsy designs
    • One mini nail file
    • One prep pad with easy instructions
    • One glue tube

     

    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: 07307-0190

    Category Name: Vacation Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Rogue Long Press On Nail Kit

    Embolden your vibe in this press on nail kit including everything you need to achieve a trendy look. The exclusive kit offers two sets of bold long press-on nails, one mini nail file, a prep pad, and glue. Follow the easy instructions on the prep pad for the best results. Complete the look with a tee and cargo pants for casual plans or travel!

    Fit & Features

    • Press on nail kit
    • Two sets of bold long press-on nails
    • One mini nail file
    • One prep pad with easy instructions
    • One glue tube

     

    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: 07307-0185

    Category Name: Vacation Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Duo Ruched Tube Crop Top

    You can't go wrong while on vacay in this tube crop top! Featuring a sleeveless V-neckline, spaghetti straps, and a ruched bust, this top is designed to flatter your figure. The elasticized ultra-cropped hem adds a trendy touch while the soft woven fabric ensures comfort while you're relaxing under the sun or having a dinner with a view! Complete the look with the matching skirt.

    Shop Matching Skirt: Flawless Duo Tiered Maxi Skirt

    Fit & Features

    • Woven fabric, bust lining, slight stretch
    • Spagehtti straps
    • Elasticized cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2469

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Duo Tiered Maxi Skirt

    You can't go wrong while on vacay in this maxi skirt! Featuring a high-rise elasticized waistband and a flowy tiered silhouette, this skirt is designed to flatter your figure. The maxi-length hem adds a trendy touch while the soft woven fabric ensures comfort while you're relaxing under the sun or having dinner with a view! Complete the look with the matching top.

    Shop Matching Top: Flawless Duo Ruched Tube Crop Top

    Fit & Features

    • Woven fabric, slight stretch
    • High-rise elasticized waist
    • Tiered flowy silhouette
    • Runs true to size

    Style Number/Barcode: 06401-0654

    Category Name: Vacation Looks

    Price: $12.97 $29.69

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Admiration Button Peplum Tank Top

    Take on a sweet look in this peplum tank top that everyone will admire! Designed to flatter with a sweetheart neckline, adjustable spaghetti straps for a custom fit, and a stretchy smocked back while the button front and peplum ruffled hem add charming details to this woven fabric. Complete the look in a trendy denim mini skirt for casual plans!

    Fit & Features

    • Woven fabric
    • Adjustable spaghetti straps
    • Stretchy smocked back
    • Button front
    • Peplum ruffled hem
    • Runs true to size

    Style Number/Barcode: 06003-2461

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Above Average Oval Metal Trim Sunglasses

    Take your look above average in these oval metal trim sunglasses perfect for driving and everyday styling! The sleek oval metal trim frame and tinted lenses provide 100% UV protection while the rubber nose supports and plastic arms ensure comfort and durability. Complete the look with a trendy shoulder bag.

    Fit & Features

    • Oval metal trim frame
    • 100% UV protection
    • Tinted lenses
    • Rubber nose supports
    • Plastic arms

    Style Number/Barcode: 07008-1056

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Icon Round Sunglasses

    Channel your classic and iconic look in these round sunglasses to shade your eyes and keep your outfit looking fab! They feature a wide round plastic frame, 100% UV protective tinted lenses, and comfortable plastic arms. Complete the look in chic stiletto pumps.

    Fit & Features

    • Round plastic frame
    • 100% UV protection
    • Tinted lenses
    • Comfortable plastic arms

    Style Number/Barcode: 07008-1054

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunniest Day Flat Top Square Sunglasses

    These flat-top sunglasses are perfect for wearing on the sunniest day! The flat top design and plastic square frame provide a unique and fashionable look while offering 100% UV protection tinted lenses for your eyes. Complete the look with a sleek shoulder bag for any occasion!

    Fit & Features

    • Plastic square frame
    • Flat top design
    • 100% UV protection tinted lenses
    • Comfortable fit

    Style Number/Barcode: 07008-1055

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everywhere Stunner Aviator Metal Sunglasses

    Everywhere you go in these aviator metal sunglasses you're sure to stun! Featuring sleek colored metal frames and tinted lenses, you'll be turning heads while enjoying 100% UV protection. Rubber nose supports and plastic arms provide comfort and durability, all in a classic aviator design. Complete the look with a dainty charm necklace.

    Fit & Features

    • Sleek-colored metal frame
    • Classic aviator design
    • 100% UV protection
    • Tinted lenses
    • Rubber nose supports
    • Plastic arms

    Style Number/Barcode: 07008-1058

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glowing Up Rhinestone Flat Jelly Sandals

    Glow up in these exclusive jelly sandals for a sparkling spring and summer! These chic sandals feature a trendy square toe and rhinestone embellished asymmetrical straps for a touch of glamour. The adjustable ankle strap with buckle closure and flat sole provides a secure and comfortable fit, while the clear jelly material with a rhinestone embellished edge trim provides a remarkable shine! Complete the look with a tote bag for a beach day or vacation!

    Fit & Features

    • Flat sole, rhinestone embellished edge trim
    • Square toe
    • Rhinestone embellished asymmetrical straps
    • Adjustable ankle strap, buckle closure
    • Clear jelly material
    • Runs true to size

    Style Number/Barcode: 07404-1202

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale