Vacation Looks

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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.

  • 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: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Timeless Satin A-Line Slip Dress

    This satin slip dress will be a forever and timeless staple! The mini dress features a sleeveless V-neck, adjustable spaghetti straps, a flattering A-line silhouette and short hem on smooth non-stretch satin fabric. Complete the look with the matching top and heels for a cocktail reception.

    Shop Matching Top: Forever Timeless Satin Collared Top

    Fit & Features

    • Sleeveless V-neck
    • Adjustable spaghetti straps
    • A-line silhouette
    • Short-length hem
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2866

    Category Name: Vacation Looks

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Bliss Floral Corset Skater Dress

    Show off your effortless beauty in this adorable floral print skater dress at weekend brunches or day dates! The corset bodice and lace-up back will snatch your waist, while the short skater silhouette gives off a flirty flair.

    Fit & Features

    • Floral printed woven fabric, woven lining with lace trim, no stretch
    • Sleeveless sweetheart neckline, lace trim, tie-front detail, ruched bust, underwire
    • Thin adjustable tank straps with lace trim
    • Corset bodice, lace trim, pleating, flexible boning
    • Lace-up back design, zipper with hook-eye closure
    • V-shaped drop waist, short skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000007

    Category Name: Vacation Looks

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Look Tie-Front Ruffled Romper

    This adorable tie-front ruffled romper will create a flirty look for your weekend plans! Designed with a lightweight woven fabric, it features a sleeveless V-neckline with a tie-front design and a keyhole cutout under the bust, spaghetti straps, dual high waist seams, flowy shorts with a mini-length overlay, and a cute fit and flare silhouette. Style with clear heels for brunch.

    Fit & Features

    • Sleeveless V-neckline, tie-front, keyhole cutout
    • Spaghetti straps, back zipper closure
    • Dual high waist seams
    • Flowy shorts, mini-length overlay
    • Fit and flare silhouette
    • Woven fabric, knit lining at the bust, minimal stretch
    • Style runs large

    Style Number/Barcode: 06403-0435

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Always Bodycon Ruffle Mini Dress

    You'll always be remembered as stunning in this mini dress, perfect for brunch or casual parties and plans! The flattering scoop neckline with a delicate rose accent adds a touch of romance, while the bodycon fit showcases your curves and is finished with a flirty ruffled hem.

    Fit & Features

    • Stretchy knit fabric, knit lining
    • Scoop neckline with a rose accent
    • Spaghetti straps
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000152

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fuzzy Feels Chenille High-Rise Jogger Pajamas

    Get cozy lounging in these chenille jogger pajamas! They feature a high-rise elasticized waistband, a skinny jogger-leg silhouette, and ribbed cuffs on ultra-soft and cozy chenille knit fabric. Complete the look in the matching pajama top and robe for a chill night in!

    Shop Matching Pajama Top: Hello Cutie Chenille Crop Pajama Top

    Shop Matching Robe: Tied In Cozy Chenille Tie-Waist Robe

    Fit & Features

    • High-rise elasticized waistband
    • Skinny jogger-leg silhouette
    • Ribbed cuffs
    • Ultra-soft chenille knit fabric
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 07103-0940

    Category Name: Vacation Looks

    Price: $13.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twice The Love Rib Knit Crop Top

    Dive into cozy rib knit love with this midi skirt! Perfect for everyday styling, this midi skirt features a high-rise elasticized waist and curve-flaunting bodycon silhouette and a side slit that shows some skin. Complete the look with the matching skirt.

    Shop Matching Skirt: Twice The Love Rib Knit Midi Skirt

    Fit & Features

    • Scoop neckline, plunging notched front design
    • Long fitted sleeves, flared hems
    • Cropped, form-hugging fit
    • Smaller notched front detail
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1806

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Table For Two Halter Mini Dress

    All eyes on you (and your table for two). With a plunging neckline and curve-hugging silhouette, this halter mini dress was made to steal the spotlight.

    Fit & Features

    • Jersey knit fabric, stretchy knit lining
    • Halter V-neck
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000312

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Inspired Charm Strapless Watercolor Print Mini Dress

    Envoke an inspired charm in this watercolor print mini dress and capture attention at parties or casual dinners!  With its strapless straight-across neckline and bodycon silhouette, this mini dress will accentuate your curves and flatter your figure. Made from airy lined mesh fabric with an eye-catching watercolor print, this dress is a must-have for any fashion-forward girlie! Complete the look in stiletto heels and a purse!

    Fit & Features

    • Watercolor print
    • Mesh fabric lined with stretchy knit
    • Strapless straight neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5605

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Shine Cubic Zirconia Circle Charm Necklace

    Give off the prettiest chic shine with this cubic zirconia circle charm necklace! It features a dainty chain with a small interlocking circle charm adorned with mini cubic zirconia stone embellishments for a subtle sparkle. Style with hoop earrings.

    Fit & Features

    • Dainty chain-link design
    • Small interlocking circle charm
    • Mini cubic zirconia stones
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1793

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Tones Smocked Eyelet Skater Dress

    Sunny tones and delicate eyelet lace embroidery? There's so much to love about this smocked skater dress that'll take you from brunch to a day date or party!

    Fit & Features

    • Eyelet lace embroidery, woven fabric lined with stretchy knit
    • Square neckline
    • Spaghetti strap ties
    • Stretchy smocked bodice
    • Skater silhouette
    • Short-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3911

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Honey, I'm Home Faux Suede Bustier

    Flaunt your fab self for your honey in this faux suede bustier featuring a strapless bodice with non-slip grip lining, flexible boning inserts, a cropped hem, and a back zipper closure. Complete the look in a sleek mini skirt and basic heels. 

    Fit & Features

    • Lined faux suede fabric, minimal stretch
    • Strapless bodice
    • Non-slip grip lining
    • Flexible boning inserts
    • Cropped hem
    • Back zipper closure
    • Runs true to size

    Style Number/Barcode: 06003-1707

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coziest Cutie Oversized Cable Knit Cardigan

    The perfect cold-weather cable knit cardigan to layer over all of your cute outfits! The sweater features slouchy long sleeves with rib knit cuffs, an open front design, and an oversized silhouette on soft and cozy cable knit fabric. Complete the look in boots for casual day or night plans!

    Fit & Features

    • Slouchy long sleeves, rib knit cuffs
    • Open front design
    • Oversized silhouette
    • Soft cable knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1827

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hello Weekend Straw Tote Bag

    This straw tote bag is ready for a summery outing! Whether you're heading to the pool, beach, or a weekend away this must-have straw bag is perfect for carrying your essentials. The bag features faux leather handles, a front embroidered "Hello Weekend", and an inner zipper closure leading to a spacious woven lined interior with a pocket. Complete the look in cute sandals.

    Fit & Features

    • Straw tote bag
    • Front embroidered "Hello Weekend"
    • Faux leather handles
    • Inner zipper closure
    • Spacious woven lined interior with pocket

    Style Number/Barcode: 07203-1969

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek One-And-Done Seamless Tank Zip-Up Catsuit

    A sleek one-and-done, this seamless catsuit is essential for layering or on its own. Perfect for lounging in stylish comfort or heading out on errands, it features a flattering scoop neckline and front zip-up closure that adds a trendy detail, and a form-hugging silhouette on seamless, stretchy rib knit fabric. Complete the look in a cozy crop jacket and booties or your favorite slippers!

    Fit & Features

    • Seamless, stretchy rib knit fabric
    • Front zip-up closure
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 07109-0358

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wow Factor Cutout Maxi Dress

    In this strapless maxi dress, you'll be checking yourself out in every mirror you pass! It boasts a metal square accent with a chic drape, a cutout bodice to show some skin, and a high front slit for effortless movement.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Strapless sweetheart neckline, metal square accent, drape design
    • Padded bra cups
    • Cutout bodice, back zipper and hook-eye closure
    • High front slit
    • Maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000116

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • Buckle Up Baby Pleated Skort

    Serving schoolgirl but make it fashionable. With sharp pleats and a bold belt moment, this skort is your go-to for flirty fits with a little edge.

    Fit & Features

    • Denim fabric, stretchy knit shorts lining
    • High-rise belted waist, side zipper and hook-eye closure
    • Pleated mini-length skirt overlay
    • Runs true to size

    Style Number/Barcode: 06603-000059

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • 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