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.

  • Higher Love Twill Wrap Denim Skort

    You'll have a high love for this twill denim skort perfect for your weekend plans! It features a high-rise waist with a side metal hoop inset and a strap belt accent, a front wrap, and a cheeky short bottom. The skort is composed of a twill denim woven fabric with no stretch. Complete the look in strappy sandals.

    Fit & Features

    • High-rise waist
    • Side metal hoop, strap belt accent
    • Side zipper closure
    • Front wrap design
    • Cheeky short bottom
    • Twill denim woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0229

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Too Glam To Care Oversized Braid Sunglasses

    These oversized sunglasses with braided arms bring instant luxe vibes. Whether you’re blocking out the sun or the shade, they’ve got your back in style.

    Fit & Features

    • Oversized sleek frames
    • Braided detail on the arms
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-000061

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready For Brunch Cork Espadrille Wedges

    These adorable cork espadrille wedges will have you ready for weekend brunch! They feature an open almond toe with a toe strap, an adjustable ankle strap with a back criss-cross design, a sturdy cork wedge heel, and a braided espadrille trim. Complete your look with a chic handbag.

    Fit & Features

    • Open almond toe, faux leather toe strap
    • Faux leather adjustable ankle strap, back criss-cross design
    • Metal buckle detail
    • Cork wedge heel
    • Espadrille trim
    • Faux leather cushioned insole
    • Runs true to size

    Style Number/Barcode: 07406-0319

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cute And Dainty Butterfly Charm Necklace

    You'll adore the cute and dainty details of this butterfly charm necklace! It features a single-row chain-link design with small clear butterfly-beaded charms. Includes an adjustable chain with a lobster clasp closure. Style with rhinestone stud earrings.

    Fit & Features

    • Single-row dainty chain-link design
    • Small clear butterfly-beaded charms
    • Adjustable chain, lobster clasp closure

    Style Number/Barcode: 07002-1480

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Glam Babe Charm Necklace Set

    Give off trendy glam babe energy in this embellished charm necklace set! It features two necklaces, including a single snake chain necklace, and a five-row layered necklace with dainty chains, mini rhinestones, and small charms featuring butterfly, star, sun, moon, and cross designs. Style this set with sleek hoop earrings.

    Fit & Features

    • Set of two necklaces
    • Single snake chain necklace
    • Five-row layered necklace
    • Dainty chains, mini rhinestones, small charms
    • Butterfly, star, sun, moon, and cross designs
    • Adjustable chains, lobster clasp closures

    Style Number/Barcode: 07002-1475

    Category Name: Vacation Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fresh 'Fit Long Sleeve Denim Romper

    Show off a fresh 'fit in this trendy denim romper! It features a collared neckline, a partial button-down front, chest pockets, long loose sleeves with cinched hems, a high waist silhouette with belt loops, fitted shorts, and a form-hugging fit. Style with cowboy boots for a cool western vibe.

    Fit & Features

    • Collared neckline, partial button-down front, chest pockets
    • Long loose sleeves, cinched hems
    • High waist, belt loops, button-front closure
    • Fitted shorts, back pockets
    • Form-hugging fit
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0309

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Muse Floral Satin Bra Top

    When it comes to your fashion style, you're a major muse for sure. This floral satin bra top is perf for you. It features a sleeveless V-neckline with a twist-front design at the bust, adjustable spaghetti straps, a stretchy smocked back panel, and a fitted cropped hem. The silky-smooth satin fabric features a chic all-over floral print pattern. Complete the look with the matching button-down top and wide-leg pants.

    Shop Matching Top: Major Muse Floral Satin Button-Down Top

    Shop Matching Bottoms: Major Muse Floral Satin Pants

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Adjustable spaghetti straps
    • Stretchy smocked back panel
    • Fitted cropped hem
    • Floral print
    • Satin woven fabric, knit lining at the bust
    • Runs true to size

    Style Number/Barcode: 06003-2198

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flowy Feels Paisley Maxi Dress

    You'll love the flowy fit of this paisley maxi dress, perfect for the warmer months! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem, and a thigh-high front slit. The smooth and stretchy knit fabric features a trendy paisley print pattern. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Maxi-length hem, high front slit
    • Flowy silhouette
    • Paisley print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4967

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Not Your Babe High-Rise Boyfriend Jeans

    You'll be brushing off all the boys when they catch sight of you in these denim boyfriend jeans perfect for flaunting all over town! They feature a flattering high-rise waist, hip-hugging silhouette, relaxed boyfriend style leg, and a clean design on premium light wash denim fabric. Complete the look in a simple corset top.

    Fit & Features

    • High-rise waist
    • Hip-hugging silhouette
    • Relaxed boyfriend-style leg
    • Front five-button fly closures
    • Five-pocket styling, belt loop accents
    • Clean premium light wash denim, no stretch
    • Runs true to size

    Style Number/Barcode: 06602-0425

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pretty As Can Be Floral Bustier

    Create your prettiest outfit yet with this floral bustier perfect for spring activities! It features a strapless curved neckline, flexible boning, side ruched seams, and a curved cropped hem. The bustier top has a floral watercolor print on mesh fabric with a cotton woven lining and no stretch. Complete the look in must-have trouser pants.

    Fit & Features

    • Strapless curved neckline
    • Side ruched seams, flexible boning
    • Back zipper and hook-eye closure
    • Curved cropped hem
    • Floral watercolor print
    • Mesh fabric, cotton woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06001-4763

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So In Love Floral A-Line Midi Dress

    You'll fall so in love with this floral midi dress to wear for day dates! It features a sleeveless square neckline, elastic ruched straps with lettuce-edge trim, an A-line silhouette, and a flirty front slit. The dress has a dainty rose floral print on stretchy knit-lined fabric. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless square neckline
    • Elastic ruched straps
    • Lettuce-edge trim
    • A-line silhouette
    • Front slit, midi-length hem
    • Dainty rose floral print, stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 05102-4921

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Taylor High-Rise Skinny Jeans By Windsor Denim

    Curve-flaunting and flattering! The Taylor jeans by Windsor denim show off your best assets and style. They feature a classic high-rise waist, front distressed accents, and on-trend knee cutouts, a skinny-leg design on premium light-wash denim fabric. Style with a flirty satin crop top and heels for a date night.

    Fit & Features

    • High-rise waist
    • Front distressed accents, knee cutouts
    • Skinny-leg design
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Light wash denim, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0323

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trip To The Tropics Printed Midi Dress

    You'll look like you're ready to whisk away on a tropical vacay in this printed midi dress! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem, a hip-hugging fit and an A-line silhouette, a thigh-high front slit, and an eye-catching tropical palm leaf print. Style with trendy wedges.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length hem, hip-hugging fit, A-line silhouette
    • High front slit
    • Tropical palm leaf print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4979

    Category Name: Vacation Looks

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Remy High-Rise Cuffed Shorts By Windsor Denim

    Let your legs out. These jean shorts by Windsor denim hug just right with plenty of stylish deets for flaunting all over social media! Featuring a flattering high-rise waist, front and back distressed accents, a cuffed fray hem, and a form-hugging fit. The shorts are composed of stretchy medium-wash denim with a color fade effect. Complete the look in trendy sandals.

    Fit & Features

    • High-rise waist
    • Front and back distressed accents
    • Cuffed fray hem, form-hugging fit
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, moderate stretch, color fade effect
    • Runs true to size

    Style Number/Barcode: 06603-0303

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Under The Sun Long Sleeve Tie-Front Crop Top

    A crochet crop top perfect for fun under the sun! The top boasts trendy flare long sleeves and a tie-front design that flaunts your figure.

    Fit & Features

    • Crochet knit fabric
    • Flare long sleeves
    • Tie-front design
    • Ultra cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2272

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Remy High-Rise Cut-Off Shorts By Windsor Denim

    Your edgy style inspo is here! Introducing your new favorite shorts by Windsor denim that flaunt your cute curves and peeks of skin. They feature a flattering high-rise waist, distressed accents, a cut-off frayed hem, and a vintage-inspired light denim fabric with minimal stretch. Complete the look in a crop top and sandals for the perfect beach day style!

    Fit & Features

    • High-rise waist
    • Distressed accents
    • Cut-off frayed hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Light wash denim, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0245

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blooming Beauty Floral Mini Dress

    You'll bloom with beauty in this effortlessly stunning floral mini dress. It features a sleeveless V-neckline, spaghetti straps that lead to an open back with a subtle strappy design, a faux wrap-front silhouette creating an asymmetric mini-length hem, and a curve-hugging fit. The stretchy knit fabric showcases a gorgeous bold floral print. Style with stilettos for a spring date night.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Open back, dual straps, single connecting bar strap
    • Faux wrap-front silhouette, asymmetric mini-length hem
    • Form-hugging fit
    • Bold floral print, knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1679

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fiercely Stylish Leopard Print Maxi Dress

    Keep it fiercely stylish with a maxi dress that brings a chic flair! The lightweight knit dress features a sleeveless V-neckline, spaghetti straps, a maxi-length, flowy, A-line silhouette, a sultry thigh-high front slit, and a trendy leopard print pattern. Complete the look with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Maxi-length A-line silhouette
    • High front slit
    • Leopard print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4968

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's So Trendy Hair Claw Clips

    Show off your trendy girl style with these of-the-moment hair claw clips! The pack features three clips, including a rectangular design, a butterfly design, and a flower design. Style these adorable clips with sleek hoop earrings.

    Fit & Features

    • Three-pack metal claw clip set
    • Rectangular design
    • Butterfly design
    • Flower design

    Style Number/Barcode: 07006-0388

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Allure Long Sleeve Lace Mini Dress

    Showcase a sweet allure in this beautiful lace mini dress! It features a sweetheart neckline with a lace-up design at the bust, sheer long balloon-style sleeves with cinched hems, ruched detailing down the side and back seams, and a mini-length hem with a curve-hugging silhouette. The partially lined lace fabric features a dainty floral embroidered pattern. Perfect for brides, style with stilettos for your engagement party or bridal shower!

    Fit & Features

    • Sweetheart neckline, lace-up design at the bust, square back
    • Sheer long balloon sleeves, elastic cinched hems
    • Ruching down the side and back seams
    • Mini-length hem, curve-hugging fit
    • Sheer lace fabric, partial knit lining, moderate stretch
    • Floral embroidered lace pattern
    • Runs true to size

    Style Number/Barcode: 05101-2025

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Go Crew Neck Slit Midi Dress

    The perfect casual midi dress to look stylish while on the go! It features cap short sleeves, a crew neck, a bodycon silhouette, a side ruched drawstring, and a flirty slit along the hem. The dress is composed of a super soft brushed knit fabric with plenty of stretch. Style with cute slide sandals and a tote bag! 

    Fit & Features

    • Cap short sleeves
    • Crew neck
    • Bodycon silhouette
    • Side ruched drawstring, slit accent
    • Midi-length hem
    • Soft brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4872

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Charm Tie-Front Midi Dress

    Make them all fall for your stylish charm in this adorable midi dress! It features a sleeveless V-neckline with a cute tie-front detail, spaghetti straps, a midi-length hem with a high front slit for a subtle sultry vibe, and a slim-fit silhouette. The lightweight knit fabric has plenty of stretch. Pair with hoop earrings and block heels for a date night.

    Fit & Features

    • Sleeveless V-neckline, tie-front detail
    • Spaghetti straps
    • Midi-length hem, high front slit
    • Slim-fit silhouette
    • Lightweight knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4864

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Irresistible Mesh Midi Dress

    You'll be a vision in this simply irresistible mesh midi dress perfect for an engagement party or cocktail soiree! It features a sleeveless plunge v-neck, adjustable straps, a back slit accent, and ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in stiletto heels.

    Fit & Features

    • Sleeveless plunge v-neck
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Ruched seams, back slit accent
    • Bodycon, midi-length hem
    • Mesh fabric, sewn-in knit lining, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1857

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Blooming Beauty Floral Midi Dress

    Bloom with beauty in this gorgeous floral midi dress perfect for the season! It features a sleeveless square neckline, spaghetti straps, a knot-front design at the waist with ruching, a midi-length hem with a chic high front slit, and a curve-hugging fit. The stretchy knit fabric showcases a stunning bold floral print. Style with platform heels for a bridal shower.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, square back
    • High waist seam, knot-front design, ruching
    • Midi-length hem, high front slit
    • Form-hugging fit
    • Bold floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1678

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free