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.

  • Swept Off Your Feet Button Ruffle Maxi Dress

    Oh-so-breezy! Sweep the room off their feet when you enter in this maxi dress featuring a sleeveless V-neckline, adjustable spaghetti straps, button-down front closures, and a flowy ruffled hem with a skin-flaunting front slit. The dress is composed of a smooth woven fabric with a sewn-in knit stretchy lining. Complete the look in espadrille wedges for a trip to the coast!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Button-down front closures
    • Front slit design
    • Flowy ruffled maxi-length hem
    • Smooth woven fabric, sewn-in knit stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5061

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Covetable Charm Strapless Mini Skater Dress

    From casual outings to chic occasions, this strapless skater dress is one you'll covet for charming looks every time! The non-slip grip lining along the strapless neckline ensures a secure fit while the ruched bodycon bodice flatters your figure. The skater silhouette and pleated short-length hem add a playful touch to this poplin dress! Complete the look in sandals and sunnies.

    Fit & Features

    • Poplin stretchy fabric, sewn-in knit lining
    • Back zipper and hook-eye closure
    • Strapless square neckline
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000035

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XXS, S, M, L

  • Plush Comfort Faux Sherpa Booties

    Step into the plush comfort of these faux sherpa booties you'll be obsessed with the coziness! Perfect for lounging at home, stepping outside, or coffee runs these booties are designed with a sturdy rubber traction sole, soft faux sherpa material, and a luxe faux fur footbed to keep extra warm. Complete the look with a cozy crop jacket.

    Fit & Features

    • Flat
    • Slip-on
    • Round
    • Rubber traction sole
    • Faux sherpa material, faux fur footbed
    • Runs true to size

    Style Number/Barcode: 07403-1758

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Girl Style Turtleneck Midi Dress

    Elevate your fall wardrobe and show off a chic girl style with this bodycon midi dress! It features a sleeveless bodice, a turtleneck, a midi-length hem with a thigh-high side slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered chain necklace and ankle booties!

    Fit & Features

    • Sleeveless bodice
    • Turtleneck
    • Midi-length hem
    • High side slit
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5096

    Category Name: Vacation Looks

    Price: $17.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Town Striped Mini Dress

    Head out of town in this stylish striped mini dress for an effortlessly cute look everywhere! Designed with a trendy twisted bust and a bodycon mini-length silhouette that perfectly flaunts your figure. Style with sandals!

    Fit & Features

    • Striped pattern, stretchy knit fabric
    • Twist sweetheart strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000029

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Sunset Happy Hour Ruffled Skater Dress

    This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.

    Fit & Features

    • Sleeveless V-neckline
    • Halter tie-back straps, open back
    • Stretchy smocked high waist
    • Short skater skirt, tiered ruffled design
    • Fit and flare silhouette
    • Twill fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-5531

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: YELLOW

    Available Size: XS, S, M, L

  • Glam Girl Sparkle Faux Leather Rhinestone Sneakers

    Get your glam girl sparkle on in these faux leather rhinestone sneakers! Featuring a round toe and lace-up placket, these sneakers are both stylish and comfortable. The chunky platform sole adds height and the rhinestone embellished heel trim adds a touch of sparkle. Complete the look with a trendy denim jacket.

    Fit & Features

    • Round toe
    • Lace-up placket
    • Chunky platform sole
    • Rhinestone embellished heel trim
    • Faux leather material
    • Runs a size bigger, recommend to size down

    Style Number/Barcode: 07407-0217

    Category Name: Vacation Looks

    Price: $28.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Step It Up Texture Knit Platform Sneakers

    Debut a new style in these casual fashion sneakers to step it up this season! Fashioned with a texture knit upper, lace-up placket, a round toe,  and a faux leather platform sole, these shoes will instantly elevate your everyday. Complete the look with a cute zip-up hoodie and latte in hand for running errands in style!

    Fit & Features

    • Round toe
    • Texture knit upper
    • Lace-up placket
    • Faux leather platform sole
    • Back pull tabs for easy on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07407-0220

    Category Name: Vacation Looks

    Price: $33.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Destination Cutie Tropical Cutout Slit Maxi Dress

    Get ready for your sunny destination with this stylish tropical maxi dress! Featuring a sweetheart neckline with a square insert, a flirty cutout bodice, and a high side slit, this dress is perfect for showing off your tropical vibes.

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Sweetheart neckline, square insert
    • Spaghetti straps
    • Cutout bodice, high side slit
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6081

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tan Lines Cutout Bodycon Mini Dress

    Flaunt your figure in this sultry strapless mini dress on vacay or a bach weekend! Designed with cutout accents and stylish hoop inserts, it creates an alluring silhouette that demands attention along the bodycon silhouette.

    Fit & Features

    • Texture knit stretchy fabric, sewn-in knit lining
    • Strapless sweetheart neckline
    • Front cutouts and hoop inserts
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000170

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, L

    Product Badge:
    • Sale
  • Girly Gingham Print Ruffled Mini Dress

    You love all things girly, so this adorable gingham print mini dress is perfect for you. The all-over smocked design adds stretch, while the ruffled neck and hem bring the cutesy vibe.

    Fit & Features

    • Smocked cotton fabric, high stretch
    • Gingham print
    • Sleeveless sweetheart neckline, ruffled trim, small bow detail
    • Adjustable spaghetti straps
    • Mini-length ruffled hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-000163

    Category Name: Vacation Looks

    Price: $44.90

    Availability: In Stock

    Available Color: GREEN

    Available Size: S, M, L

  • Fine Dime Rhinestone Strap Block Heel Mules

    Slip into these fine metallic mules for an elevated and glamorous style! They feature a square toe, dual rhinestone embellished straps, and a block heel. Complete the look with an embellished clutch purse for a dressy evening out!

    Fit & Features

    • Square toe
    • Dual rhinestone embellished straps
    • Block heel
    • Metallic material
    • Runs true to size

    Style Number/Barcode: 07401-4629

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Eyes on You Lace Low Back Midi Dress

    Soft girl era, but make it spicy. With a sheer midi hem, sultry low back, and flirty side slit, this is the “accidentally iconic” dress for nights out, beach dates, or brunches.

    Fit & Features

    • Stretch lace knit fabric, partially lined
    • V-neckline, spaghetti straps
    • Low back cut
    • Curve-hugging silhouette
    • Sheer midi hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000222

    Category Name: Vacation Looks

    Price: $46.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Oh Snap Button Henley Bodysuit

    Slay all day in this essential henley bodysuit you'll love styling with day or night fits! The sweater rib knit bodysuit features long fitted sleeves, a plunge V-neckline, three snap-button front closures, and a thong-cut bottom with snap-button closures. Complete the look in new denim jeans and knee-high boots.

    Fit & Features

    • Long fitted sleeves
    • Plunge V-neckline
    • Three snap-button front closures
    • Thong bottom
    • Dual snap-button closures
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1592

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachy Breeze Strapless Slit Maxi Dress

    Enjoy a sunset dinner by the beach in this chic strapless maxi dress showcasing a high slit for effortless movement and a flattering bodycon silhouette.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, twist accent
    • Bodycon silhouette
    • High side slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000052

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S, M, L

  • Eye-Catching Pop Strappy Thong Stiletto Sandals

    Perfect for adding eye-catching style, these stiletto sandals give every outfit the pop it needs! With a square toe, thong toe strap, and short stiletto heel, these faux leather sandals are as stylish as they are comfortable. The strappy adjustable ankle with buckle closure adds an elevated allure and a secure fit. Complete the look with a trendy shoulder bag for any occasion!

    Fit & Features

    • 3.5" Stiletto heel
    • Faux leather material
    • Thong toe strap
    • Strappy adjustable ankle, buckle closure
    • Runs true to size

    Style Number/Barcode: 07401-4838

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In Tulum One-Shoulder Tropical Maxi Dress

    Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing! 

    Fit & Features

    • Tropical print, smooth knit fabric with short stretchy lining
    • One-shoulder neckline
    • One shoulder strap with metal accents
    • Front ruffled slit
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6073

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS

    Product Badge:
    • Sale
  • Constant Stunner Open Back Halter Crop Top

    You'll always stun in this sexy halter crop top boasting an open back and front design that leaves many speechless!

    Fit & Features

    • Eyelet floral embroidery, woven-lined fabric
    • Halter plunge neckline
    • Open front design
    • Cropped hem
    • Open back with spaghetti strap tie
    • Runs true to size

    Style Number/Barcode: 06003-2742

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold Vibe Floral Print Strapless Bodycon Mini Dress

    Look gorgeous at your getaway and show off a bold vibe in this knit mini dress designed with a large floral print to turn heads. It features a strapless straight-across neckline and a short bodycon silhouette to hug your curves.

    Fit & Features

    • Smooth knit fabric with knit lining, plenty of stretch
    • Large floral print
    • Strapless straight neckline, no-slip strip
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000193

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Chic Twist Tie-Back Striped Midi Dress

    A chic twist on a classic sundress. This head-turning midi dress is designed with an open tie-back with button accents and hidden side pockets that keep your hands warm!

    Fit & Features

    • Striped print, woven fabric, woven lining
    • V-neckline
    • Spaghetti straps
    • Open tie-back design, lower button accents
    • Hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000022

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Playful Summer Sweetheart Ruffled Eyelet Midi Dress

    Looking for the perfect summer dress? Look no further than this playful sleeveless midi dress! With its flattering sweetheart neckline with a structured bust and adjustable spaghetti straps, this A-line silhouette dress will have you feeling confident and stylish. The ruffled midi-length hem and floral embroidered eyelet woven fabric add a touch of playfulness to this must-have dress! Complete the look with wedge sandals.

    Fit & Features

    • Floral embroidered eyelet woven fabric, stretchy knit lining
    • Sweetheart neckline, padded bust with underwire
    • Adjustable spaghetti straps, back zipper with hook and eye closure
    • High waist seam, A-line silhouette
    • Ruffled midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3015

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Mood Strappy Faux Leather Block Heel Mules

    These strappy faux leather block heel mules will put you in a chic mood! The low-block heels are composed of smooth faux leather material and feature an open square-shaped toe with a thin knotted strappy design across the foot for a trendy look. Include an open back for easy on-and-off styling. Pair these mules with a mini handbag!

    Fit & Features

    • 3" Block heel
    • Faux leather material
    • Open square toe
    • Knotted strappy design
    • Open back
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4760

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kiss The Sun Tropical Lace-Up Slit Maxi Dress

    Sipping a mai tai oceanside has never looked cuter in this tropical maxi dress! Made to turn heads, this maxi dress boasts a sexy lace-up back, form-hugging silhouette that shows off your curves, and a high front slit giving major allure.

    Fit & Features

    • Tropical print, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Lace-up back
    • Form-hugging silhouette, high front slit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6103

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine Cutie Strapless Ruffle Eyelet Mini Dress

    Created for the cuties, this eyelet mini dress is a cute look for shower celebrations or casual parties! Designed to hug your form for a flattering fit, the strapless neckline and ruffled mini hem add a flirty and playful touch.

    Fit & Features

    • Eyelet fabric, stretchy knit lining
    • Strapless neckline
    • Form-hugging fit
    • Ruffled layer mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000187

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free