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.

  • So Darling Ditsy Floral Puff Sleeve Crop Top

    Create a sweet look that is oh-so-darling with this disty floral printed crop top! It features a sweetheart neckline with a twist-front design at the bust, short puff sleeves with ruffled trims, tie-back straps, and a fitted, cropped hem. The lightweight woven fabric features an adorable dainty ditsy floral print pattern. Style with the matching flowy shorts for the perfect brunch outfit.

    Shop Matching Bottoms: So Darling Ditsy Floral Flowy Shorts

    Fit & Features

    • Sweetheart neckline, twist-front design at the bust
    • Short puff sleeves, elasticized hems, ruffled trims
    • Tie-back straps
    • Fitted, cropped hem
    • Ditsy floral print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1797

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Occasion Satin Collared Button-Down Romper

    Make your next party a chic occasion in this silky sleek satin romper! It features a collared neckline, short sleeves, a button-down front, buttoned chest pockets, a cinched waist with a faux tie-front design, front pockets, and relaxed-fitting shorts. The smooth satin woven fabric gives off a stunning sheen to amp up the chic factor. Style with a chunky chain-link necklace and clear mules.

    Fit & Features

    • Collared neckline, short sleeves
    • Button-down front
    • Dual buttoned chest pockets
    • Cinched high waist, faux tie-front
    • Dual front pockets, relaxed-fitting shorts
    • Silky satin woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0334

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Just Spotted Leopard Lace-Up Midi Dress

    Just spotted, you in this effortlessly fierce leopard print midi dress! It features a sleeveless V-neckline with a twisted bust accent, spaghetti straps that lace up in the back, and a flattering A-line silhouette with a flowy hem. Complete the look with a sleek choker for lunch with friends!

    Fit & Features

    • Sleeveless V-neckline, twisted bust accent
    • Spaghetti straps, lace-up back
    • A-line silhouette
    • Flowy midi-length hem
    • Leopard print, breezy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4976

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What A Girl Wants V-Neck Mini Dress

    What a girl wants is this casual mini dress perfect for styling up or down! The dress features a sleeveless V-neckline, wide shoulder straps, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in stunning lace-up heels for a party.

    Fit & Features

    • Sleeveless V-neckline
    • Wide shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5100

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Decision V-Neck Cutout Maxi Dress

    A maxi dress you can style up or down? That's an easy decision! It features a sleeveless V-neckline, spaghetti straps, a knotted bust with cutout sides and back, and a hip-hugging slim silhouette with a sultry high-side slit on stretchy rib knit fabric. Complete the look in trendy sandals for a beach club or vacation!

    Fit & Features

    • Sleeveless V-neckline, knotted bust, spaghetti straps
    • Side and back cutouts
    • Hip-hugging, slim silhouette
    • High side slit
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5094

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Strut Lace-Up Platform Block Heels

    Showcase a chic strut in these cool-girl platform block heels. They feature an open square-shaped toe, a thin strappy design with knotted accents, lace-up straps that wrap around the leg, a platform sole, and a chunky block heel. Style with a mini handbag.

    Fit & Features

    • Open square-shaped toe
    • Thin strappy design, knotted details
    • Lace-up strappy wrap-around design, tie closure
    • Open back
    • Platform sole, thick block heel
    • Faux leather material, subtle cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4240

    Category Name: Vacation Looks

    Price: $29.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • For A Spin Rhinestone Spiral Flat Sandals

    Take these luxe sandals out for a glamorous spin! Day or night, they're perfect for a classic GNO, wedding, or semi-formal event. Featuring a square toe, metallic flat sole with mini rhinestone trim, thin toe rhinestone straps, and a spiral ankle strap with rhinestone embellishments. Complete the look with a clutch purse.

    Fit & Features

    • Square toe
    • Metallic flat sole, mini rhinestone trim
    • Thin toe rhinestone straps
    • Spiral ankle rhinestone strap
    • Runs true to size

    Style Number/Barcode: 07404-1148

    Category Name: Vacation Looks

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Best Vibes Mid-Rise Denim Skort

    Give off the best style vibes in this breezy denim skort perfect for casual summer plans! It features a flattering mid-rise waist, a bodycon silhouette, a skirt-like front design, and a short-length hem on stretchy medium wash denim. Complete the look in a basic tank top and sandals.

    Fit & Features

    • Mid-rise waist
    • Bodycon silhouette
    • Skirt-like front design, short-length hem
    • Front dual button and hidden zipper closure
    • Three-pocket styling, belt loop accents
    • Medium wash denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06603-0337

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coastal-Chic Woven Straw Belt

    Accessorize your summer looks with this on-trend belt for a coastal-chic vibe. It features a woven straw design with a round buckle. Style with a crop top and distressed denim shorts.

    Fit & Features

    • Woven straw design
    • Round metal buckle

    Style Number/Barcode: 07301-0635

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Alert Cutout High Slit Mini Dress

    Get ready to flirt up a storm in this cutout high slit mini dress that will bring that sultry allure. It features a sleeveless square neckline, spaghetti straps, an asymmetric side cutout at the waist to show off some skin, a mini-length hem with a high-cut side slit, and a fitted A-line silhouette. The brushed knit fabric offers plenty of stretch. Style with lace-up heels for a night out.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Asymmetric side cutout at the waist
    • Mini-length hem, high-cut side slit
    • Fitted A-line silhouette
    • Double-lined brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-5045

    Category Name: Vacation Looks

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Symphony Floral Maxi Skirt

    This floral maxi skirt brings perfect tropical vibes to your weekend plans or vacation! Pair with the matching top to complete the look.

    Shop Matching Top: Perfect Symphony Floral Tube Top

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • High-rise waist
    • Curve-hugging silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000043

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stripe It Right Crepe Tie-Front Crop Top

    Trend right with this breezy striped crepe top essential for summer! It features bell long sleeves, a plunge V-neckline, and a flirty tie-front closure along the ultra-cropped hem. Complete the look in high-waisted jeans for exploring a beach city.

    Fit & Features

    • Bell long sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Ultra cropped hem
    • Striped print
    • Crepe fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1348

    Category Name: Vacation Looks

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 2000s Babe Rhinestone Denim Bucket Hat

    Channel that 2000s babe energy with this trendy denim bucket hat! It features a classic bucket hat design with a wide brim and all-over mini rhinestone embellishments for a stylish sparkle. Pair with a graphic tee and low-rise jeans!

    Fit & Features

    • Classic bucket hat design
    • Wide brim
    • Mini rhinestones
    • Denim material

    Style Number/Barcode: 07302-1460

    Category Name: Vacation Looks

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Beauty Butterfly Layered Necklace Set

    Adorn your semi-formal dress with this whimsical necklace set! It features a layered design with a butterfly charm, dainty flower charms, and multi-colored beads. Complete the look in a flirty skater dress for a rehearsal dinner or celebration!

    Fit & Features

    • Layered necklace
    • Butterfly charm
    • Dainty flower charms
    • Multi-colored beads
    • Sleek chain link string
    • Losber clasp closure

    Style Number/Barcode: 07002-1504

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Perfect Basic Knit Mini Dress

    This casual knit mini dress is the perfect basic for creating cute everyday 'fits! It features a V-neckline, short fitted sleeves, a mini-length hem, and a form-hugging fit. The cotton-blend fabric offers a moderate stretch. Style with hoop earrings and strappy mules.

    Fit & Features

    • V-neckline
    • Short fitted sleeves
    • Mini-length hem
    • Form-hugging fit
    • Cotton-blend smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5050

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Stroll Rib Knit Midi Dress

    Take a casual stroll looking cute in this rib knit midi dress essential for afternoon pick-me-ups with the girls! Featuring a sleeveless square neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the hem. Complete the look with a layered choker necklace.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Form-hugging silhouette
    • Front slit
    • Midi-length hem
    • Rib knit fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5183

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Mode Tropical V-Neck Midi Dress

    Enter vacay mode with the perfect tropical midi dress that'll have you looking fabulous! It features a sleeveless V-neckline, adjustable spaghetti straps, a form-hugging silhouette, and a sultry side slit cutout. Complete the look in chic mules for a dinner by the beach!

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps
    • Form-hugging silhouette
    • Side slit cutout, slit
    • Midi-length hem
    • Tropical palm leaf print, stretchy knit fabric, bust lining
    • Runs true to size

    Style Number/Barcode: 05102-5056

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Miami Mood Tropical Print Cutout Maxi Dress

    This alluring tropical print maxi dress is an iconic pick for a summer vacay to Miami! It features a sleeveless halter neckline with cross-front straps, a sultry center bust cutout followed by a chic O-ring accent, dual waist cutouts on each side, a backless design with dual tie-back straps, a floor-length hem with dual thigh-high front slits, and a flowy A-line silhouette. The lightweight woven fabric showcases an all-over tropical palm leaf pattern. Style with hoop earrings and clear mules.

    Fit & Features

    • Sleeveless halter neckline, cross-front straps, tie-back design
    • Center bust cutout, O-ring accent, dual waist cutouts
    • Backless design, dual tie-back straps, elasticized back waistband
    • Floor-length hem, dual high front slits, A-line silhouette
    • Tropical palm leaf print
    • Woven fabric, lined bust, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5087

    Category Name: Vacation Looks

    Price: $5.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie The Knot Rhinestone Flat Sandals

    Tie your outfit together by sliding into these statement-flat sandals! Featuring a round toe, a PVC clear strap with multiple rhinestone embellished straps that form a trendy knot design, and a faux leather footbed. Style with a chic ring set for added sparkle!

    Fit & Features

    • Round toe
    • PVC clear strap
    • Multiple rhinestone embellished straps, knot design
    • Faux leather footbed
    • Flat sole
    • Runs a 1/2 size bigger

    Style Number/Barcode: 07404-1127

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual-Chic Style Muse High Slit Maxi Dress

    Show off your elevated casual-chic style in this high slit maxi dress. Featuring a sleeveless crew neckline with tank shoulder straps, trendy side cutouts at the waist, a maxi-length hem, and a thigh-high side slit, this dress will get you major compliments. The ribbed knit fabric offers plenty of stretch. Complete the look with sleek hoops and strappy heels.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Dual side cutouts at the waist
    • Maxi-length hem
    • High side slit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4866

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel The Breeze Palm Print Mesh Duster

    Feel the island breeze everywhere you go in this palm print duster featuring long sleeves, an open front design, and a flowy silhouette on sheer mesh fabric. Layer over a basic bodysuit and denim shorts for a cute vacation look!

    Fit & Features

    • Long sleeves
    • Open front design
    • Flowy silhouette
    • Duster length hem
    • Palm print
    • Sheer mesh fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06202-0405

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple And Sultry Cutout Midi Dress

    Simple and sultry, this cutout midi dress will make a chic impression. It features a sleeveless V-neckline with ruching and a center O-ring accent, spaghetti straps, a front waist cutout, a midi-length hem with a thigh-high front slit, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with lace-up heels.

    Fit & Features

    • Sleeveless V-neckline, ruched, center metal O-ring accent
    • Spaghetti straps
    • Front waist cutout, high waist
    • Midi-length hem, high front slit
    • Curve-hugging fit
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2298

    Category Name: Vacation Looks

    Price: $5.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Artsy Abstract Print Cutout Jumpsuit

    You'll be feelin' artsy and chic in this alluring abstract print jumpsuit. It features a sleeveless plunging V-neckline with a padded bust, halter spaghetti straps with a tie-back design, and a small center cutout with a metal accent under the bust. The waist has dual cutouts on each side with chunky chain-link accents connected to straps for a bold vibe, an open back with dual tie-back straps, and a wide-leg silhouette with a relaxed fit. The woven fabric showcases an all-over multi-colored abstract print pattern that will catch everyone's eye. Style with espadrille sandals.

    Fit & Features

    • Sleeveless plunging V-neckline, padded bust
    • Halter spaghetti straps, tie-back design
    • Small center cutout under the bust, metal accent
    • Dual waist cutouts, chain-link accents connected to straps
    • Open back, dual tie-back straps, lower back zipper, hook and eye closure
    • Wide-leg silhouette, relaxed fit
    • Multi-colored abstract print, woven fabric, knit lining at the bust, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06402-1326

    Category Name: Vacation Looks

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Weekend Plans Wide-Leg Pants

    These airy and chic wide-leg pants are perf for your casual weekend plans. They feature a high-rise elasticized waist, a faux front drawstring, dual front pockets, and a relaxed fit with a wide-leg silhouette. The lightweight gauze fabric has no stretch. Style with a crop top and sandals for a breakfast date.

    Fit & Features

    • High-rise elasticized waist
    • Faux front drawstring
    • Dual front pockets
    • Relaxed fit, wide-leg silhouette
    • Gauze fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0778

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance