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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.

  • 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: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Tropical Blooms Flower Hair Claw Clip

    Vacay mode activated! Show off these tropical flower hair claw clips while on your getaway or a chic pool party.

    Fit & Features

    • Tropical flower
    • Claw clip closure

    Style Number/Barcode: 07006-000060

    Category Name: Vacation Looks

    Price: $7.90

    Availability: In Stock

    Available Color: YELLOW, WHITE, BLUE, PURPLE

    Available Size: NS

  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romance In Bloom Floral Tie-Front Top

    A top that’s equal parts sweet and sultry. With a tie-front and ruffle trim, this floral top is your go-to for brunch, concerts, or just serving soft-girl vibes all season.

    Shop Matching Bottoms: Romance In Bloom Floral Ruffle Skort

    Fit & Features

    • Floral print lace-lined fabric
    • Cap sleeves
    • Open front design with tie closure
    • Ruffled trim
    • Cropped-length hem
    • Runs true to size

    Style Number/Barcode: 06202-000051

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: M, L

    Product Badge:
    • Sale
  • Flawless Vibes V-Neck Cutout Wide-Leg Jumpsuit

    Arrive looking flawless in this wide-leg jumpsuit for dinner and drinks on vacay or a rooftop party! Featuring a flattering V-neckline and spaghetti straps, this jumpsuit also boasts an O-ring bust insert and cutout bodice for a trendy touch leading to the wide-leg silhouette. Complete the look with heels.

    Fit & Features

    • Texture knit fabric, minimal stretch
    • Spaghetti straps
    • V-Neckline, O-ring insert
    • Cutout bodice
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2507

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • True Devotion Strapless Ruffle Skater Mini Dress

    Express your true devotion to flirty style in this strapless skater dress perfect for strolling a beach city or a brunch! Featuring a flattering strapless neckline with a tie and stretchy elasticized bands for a comfortable, secure fit. The skater silhouette and ruffled mini-length hem add a touch of flirty fun. Complete the look in strappy sandals.

    Fit & Features

    • Cotton woven fabric with non-stretch lining
    • Strapless neckline with tie
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5711

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Style Striped Knit Halter Crop Top

    This cute striped halter crop top will stylishly elevate your casual weekend 'fits. Made with a stretchy striped ribbed knit fabric, it features a plunging V-neckline with a trendy tie-front design, a halter strap leading to a partially open back, and a cropped hem with a form-hugging fit. Pair with jean shorts and sneakers.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Plunging V-neckline
    • Tie-front
    • Halter strap
    • Cropped
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06002-1870

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chasing Butterflies Belly Chain

    Chase this flirty belly chain to adorn your swimsuit or midriff outfit! The belly chain features a trendy layered design with butterfly charms and a ball chain fastened with a lobster clasp closure. Complete the look with a pair of sandals.

    Fit & Features

    • Layered belly chain
    • Butterfly charms
    • Ball chain 
    • Lobster clasp closure

    Style Number/Barcode: 07002-1833

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can U Not Crew Neck Crop Tee

    Tell it like it is with this sassy crop tee! It features short sleeves, a crew neck, embroidered "Can U Not" lettering across the front, and a fitted crop hem to flaunt your figure. Complete the look in a mini skirt for extra attitude!

    Fit & Features

    • Stretchy rib knit fabric
    • Crew neckline
    • Embroidered "Can U Not" lettering
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06002-1835

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Trendsetter Open Weave Tote Bag

    Breezy and on-trend, this tote bag is made with an open weave design for that perfect casual weekend style. It features long dual top handles and a removable woven pouch with a drawstring closure to keep your essentials secure.

    Fit & Features

    • Open weave design
    • Long dual top handles
    • Removable woven pouch, drawstring closure

    Style Number/Barcode: 07203-2119

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS

  • Vacay Muse Tropical Floral Knit Bodycon Mini Dress

    You'll be a gorgeous vacay muse in this tropical floral mini dress! The sleek stretchy knit fabric showcases a blooming tropical floral print perfect for your summer trips. The short dress features a sleeveless square neckline, spaghetti straps, an alluring ruched waist cutout with an adjustable drawstring, and a bodycon silhouette to flaunt your figure. Style with espadrille wedges.

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric
    • Square neckline
    • Spaghetti straps
    • Ruching waist cutout, drawstring
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5614

    Category Name: Vacation Looks

    Price: $11.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Charm Crochet Seashell Trim Crop Top

    Add the perfect beachy touch with this rib knit crop top! The crew neck adds a modern touch, while the crochet and seashell trim exude a unique coastal vibe. 

    Fit & Features

    • Rib knit stretchy fabric
    • Crew neckline
    • Curved crop hem, crochet and seashell trim
    • Runs true to size

    Style Number/Barcode: 06002-000060

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free