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.

  • Power Moves Button Woven Vest

    Make power moves and take your style to a polished level in this button-up woven vest. Pair with the matching bottoms to complete the look.

    Fit & Features

    • Woven fabric, sewn-in woven lining
    • Button-up front closures
    • Stretchy smocked back
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Bottoms: Power Moves High-Rise Trouser Pants

    Style Number/Barcode: 06204-2104

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: IVORY, LIGHT, BLUE

    Available Size: S, M, L, XS

    Product Badge:
    • Part of a Set
  • Summertime Chic Strappy Espadrille Wedges

    Level up your summertime 'fits with these chic strappy espadrille wedges. They feature an on-trend woven espadrille wedge heel, an open square-shaped toe, an asymmetric strappy design across the foot, and thin adjustable ankle and heel straps for a customized fit with a buckle closure. Style with a floral dress for weekend brunch!

    Fit & Features

    • 4" Espadrille wedge heel
    • Faux leather upper
    • Open square toe
    • Asymmetric strappy design
    • Adjustable ankle and heel straps, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07406-0338

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrap Around The Block Strappy Platform Sandals

    Take a stylish walk around the block in these platform sandals featuring a round toe, asymmetrical faux leather strap, and an adjustable ankle strap with buckle closure. Complete the look in a breezy maxi dress for vacation or weekend plans!

    Fit & Features

    • Round toe
    • Asymmetrical faux leather straps
    • Platform sole
    • Adjustable ankle strap with buckle closure
    • Runs true to size

    Style Number/Barcode: 07404-1234

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Mood Crochet Cropped Sweater

    This cropped sweater is designed with a breezy open crochet knit fabric, creating a bold sheer look perf for weekend getaways. It features a wide boat neckline and long bell sleeves to give off those effortlessly chic vibes. Style with the matching maxi skirt.

    Shop Matching Bottoms: Weekend Mood Crochet Maxi Skirt

    Fit & Features

    • Open crochet knit fabric, minimal stretch
    • Boat neckline
    • Long bell sleeves
    • Cropped hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06005-2113

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Summer Cutie Chambray Floral Romper

    Effortlessly cute for summer, this chambray romper flaunts an adorable embroidered floral pattern and flowy shorts perfect for styling with sandals.

    Fit & Features

    • Cotton-blend chambray fabric, woven lining, no stretch
    • Floral embroidered pattern
    • Sleeveless square neckline, ruched bust, spaghetti strap ties
    • Smocked back, zipper with hook-eye closure
    • Fitted bodice, high-rise waist, flowy shorts bottom
    • Romper in size small is 28" shoulder to hem with a 14" front rise and a 1.5" inseam
    • Runs true to size

    Style Number/Barcode: 06303-000003

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

  • Getaway Attitude Off-The-Shoulder Crochet Top

    Serve a cute attitude for your next getaway in this off-the-shoulder crochet top. Crafted from sheer crochet knit fabric that brings dreamy vibes, this top features long bell sleeves, a bungee halter strap with beading that creates the front adjustable ruching so you customize the style, and a cropped hem. Complete the look in printed flare pants for a vacay or festival!

    Fit & Features

    • Sheer crochet knit, bust lining
    • Off-the-shoulder
    • Bungee halter strap with beading
    • Adjustable ruching
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5097

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Slay Strapless Cutout Mini Dress

    Serve a sultry slay in this curve-hugging mini dress designed with a strapless neckline, ruched detailing, and an open lower back with an O-ring cutout for a trendy allure.

    Fit & Features

    • Smooth double-lined knit fabric, high stretch
    • Strapless straight-across neckline
    • Ruching
    • Open lower back, O-ring cutout
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000065

    Category Name: Vacation Looks

    Price: $38.90

    Availability: In Stock

    Available Color: TURQUOISE

    Available Size: XS, S, M, L

  • Flirty Match High-Rise Palazzo Pants

    Flirt up your style in these palazzo pants on vacation or weekend fun! The high-rise waist and wide-leg silhouette provide a flattering fit, while the flowy design adds a touch of playful charm. Complete the look with the matching top.

    Shop Matching Top: Flirty Match Short Sleeve Tie-Front Top

    Fit & Features

    • Woven fabric, no stretch
    • High-rise elasticized waist
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1396

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romantic Icon Retro Heart Sunglasses

    Be seen as a romantic icon in these retro heart sunglasses! They feature a heart-shaped design with trim, and tinted lenses to help protect your eyes, metal arms, and nose supports for comfortable wear. Complete the look in a scoop neck bodysuit and denim shorts for a backyard BBQ or summer pool party!

    Fit & Features

    • Heart-shaped design with trim
    • Tinted lenses
    • Metal arms
    • Nose supports

    Style Number/Barcode: 07008-1085

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Perfection Ruffled Floral Chiffon Maxi Skirt

    Be gorgeous and perfect all season in this floral chiffon maxi skirt at formal soirees! Made with floral and leaf print chiffon fabric, this skirt is a must-have for any fashion-forward girlie. Its high-rise waist and tiered ruffled silhouette create a flattering fit, while the maxi-length hem adds a chic touch. Complete the look with the matching top.

    Shop The Matching Top: Gorgeous Perfection Halter Floral Chiffon Crop Top

    Fit & Features

    • Floral and leaf print, chiffon fabric lined with stretchy knit
    • High-rise waist
    • Back zipper and hook-eye closure
    • Tiered ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 06401-0685

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Cool Long Sleeve Denim Romper

    Capture a casually cool vibe for your weekend plans in this long sleeve denim romper! It features a structured collared neckline, long sleeves with snap button closures, a snap button-down front, dual buttoned chest pockets and side pockets, a stylish cuffed hem, and a relaxed fit for an effortlessly on-trend look. Pair with hoop earrings and sneakers!

    Fit & Features

    • Non-stretch denim fabric
    • Collared neckline
    • Long sleeves with snap button closures
    • Snap button-down front
    • Buttoned chest pockets, side pockets
    • Cuffed hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06303-0286

    Category Name: Vacation Looks

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Cool High-Rise Denim Skort

    Keep your everyday 'fits casually cool with this high-rise denim skort featuring a mini-length overlay with a faux wrap-front design and hidden shorts. Style with a graphic tee and sneakers!

    Fit & Features

    • Cotton-blend denim fabric, minimal stretch
    • High-rise waist
    • Back zipper with hook-eye closure, dual back pockets
    • Mini-length overlay, faux wrap-front design, short slit
    • Hidden fitted shorts
    • Skort in size small has a 9.5" front rise with a 2" inseam
    • Runs true to size

    Style Number/Barcode: 06603-000005

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L, XL

  • Stunning One Halter V-Neck Ruffle Floral Maxi Dress

    You'll take every vacation or summer party by storm when you have this floral maxi dress! This stunning maxi dress features a halter V-neckline with spaghetti strap tassel ties, a stretchy smocked bodice accentuating your figure, and hidden side pockets for added convenience. The flowy ruffled silhouette and floor-length hem add a stylish finish. Complete the look in sandals and sunglasses!

    Fit & Features

    • Floral print, woven fabric with lining, no stretch
    • Halter V-neckline
    • Spaghetti strap tassel ties
    • Stretchy smocked bodice
    • Flowy ruffled maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5776

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Aesthetic Strapless Tie Back Paisley Maxi Dress

    Channel a boho aesthetic in this paisley maxi dress for carefree summer days! With its strapless neckline and tie-back design, this maxi dress hugs your curves and flows effortlessly with a beautiful paisley print on knit fabric with chiffon lining. Complete the look with earrings for a dressy summer party! 

    Fit & Features

    • Paisley print, knit fabric lined with chiffon
    • Strapless neckline
    • Tie back design
    • Form-hugging maxi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3400

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Mood Crochet Maxi Skirt

    This maxi skirt is designed with a breezy open crochet knit fabric, creating a bold sheer look perf for weekend getaways. It features a high-rise elastic waist for added stretch and a maxi-length slim-fit silhouette with a flared-out hem for that effortlessly chic vibe. Style with the matching cropped sweater.

    Shop Matching Top: Weekend Mood Crochet Cropped Sweater

    Fit & Features

    • Open crochet knit fabric, minimal stretch
    • High-rise elastic waist
    • Maxi-length slim-fit silhouette
    • Flared-out hem
    • Runs true to size

    Style Number/Barcode: 06501-1076

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine On Me Chandelier Earrings

    Catch the light and the spotlight. These cascading chandelier earrings bring all the bold energy with a sculptural shape that turns any outfit into a moment.

    Fit & Features

    • Tiered chandelier design
    • Textured metal teardrop-shaped silhouette
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000020

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Open Toe Season Lace-Up Espadrille Wedges

    As the weather starts warming up these espadrille wedges are perfect for showing off your fresh pedicure in style! Featuring a chic faux leather square toe and playful criss-cross straps to elevate any outfit. The checkered embroidered ankle strap with lace-up ties adds a touch of whimsy to these shoes. Complete the look with a tote bag for a backyard party or beach day!

    Fit & Features

    • 4" Espadrille Wedge Heel
    • Faux leather square toe and criss-cross straps
    • Lace-up ties
    • Checkered embroidered ankle strap
    • Runs true to size

    Style Number/Barcode: 07406-0354

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Passion V-Neck Color Block Maxi Dress

    Dress to impress in this V-neck maxi dress to make a chic impression at parties or rehearsal dinners! The flowy silhouette and color block panels give you a stunning look, while the spaghetti straps and neck tie add a trendy touch. Complete the look with a clutch and heels.

    Fit & Features

    • Woven fabric, no stretch
    • V-neck
    • Spaghetti straps, spaghetti strap neck tie
    • Color block panels, flowy silhouette
    • Maxi length
    • Runs true to size

    Style Number/Barcode: 05102-5803

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getaway Retreat High Rise Tropical Pants

    Getaway in these tropical pants for the sweetest vacay vibe! These pants feature a high rise drawstring waist so you customize the fit, side pockets for keeping your hands warm, and a flattering straight-leg silhouette. Complete the look with the matching top.

    Shop The Matching Top: Getaway Retreat Sweetheart Tropical Crop Top

    Fit & Features

    • Tropical print, woven fabric
    • High rise drawstring waist
    • Side pockets
    • Straight leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1397

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Served Tie-Front Crop Top

    Serve flirty without saying a word. This rib knit tie-front top is giving effortlessly hot with a fitted silhouette that’s made for coffee runs, early brunches, and everything in between.

    Fit & Features

    • Stretchy rib knit fabric
    • Short sleeves
    • Tie-front design
    • Ultra cropped fitted hem
    • Runs true to size

    Style Number/Barcode: 06202-000022

    Category Name: Vacation Looks

    Price: $19.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Feeling Myself High Neck Lace-Up Knit Maxi Dress

    Feel yourself in this trending sleeveless knit maxi dress while on vacation or weekend plans! Made with stretchy textured knit fabric, it's perfect for any occasion. This bodycon dress features a high neckline and spaghetti straps for a sleek look, while the lace-up back turns heads. Complete the outfit in stiletto heels.

    Fit & Features

    • Textured knit fabric, stretchy knit lining
    • High neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-1960

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Social Outing Sleeveless Belted Cargo Crop Jumpsuit

    Pencil in casual plans with friends in this sleeveless jumpsuit for a stylish 'fit! The square neckline and adjustable spaghetti straps keep you comfortable while the adjustable belted waist flatters your figure. Plus, the cargo pockets add a touch of functionality to the wide-leg silhouette. Complete the look in platform sneakers.

    Fit & Features

    • Woven fabric, partial lining, slight stretch
    • Adjustable spaghetti straps, square neckline
    • Back zipper and hook-eye closure
    • Adjustable waist belt
    • Side pockets, cargo pockets
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0821

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off To Paradise Wide-Leg Abstract Pants

    A trending abstract pants designed with a flattering high-rise waist and a wide-leg design that flaunts your figure on vacay! Pair with the matching top to complete the look.

    Fit & Features

    • Abstract print, stretchy knit fabric
    • High-rise waist
    • Wide-leg silhouette
    • Runs true to size 

     

    Shop The Matching Top: Off To Paradise Tie-Front Crop Top

    Style Number/Barcode: 06502-000010

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Lover's Knot Stud Earrings

    Made with exquisite knot details, these earrings are the perfect symbol of how much you'll love them!

    Fit & Features

    • Knot design
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged

    Style Number/Barcode: 07001-000083

    Category Name: Vacation Looks

    Price: $7.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free