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.

  • On Your Radar Mirrored Aviator Sunglasses

    These trendy aviator sunglasses definitely need to be on your radar! They feature an aviator design with a thin metal frame, thin metal arms, and mirrored lenses. Style with a graphic tee for an edgy-chic look.

    Fit & Features

    • Aviator design
    • Thin metal frame, metal arms
    • Mirrored lenses
    • Rubber nose supports
    • 100% UV protection

    Style Number/Barcode: 07008-0983

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sent You A Text Square Neck Mini Dress

    You might want to reply back to your new favorite casual mini dress for weekend outings or day dates! It features a sleeveless square neck, tank-style straps, and a bodycon silhouette, and is composed of a textured fabric with a stretch knit lining. Style with a denim jacket and sandals.

    Fit & Features

    • Sleeveless square neck
    • Tank-style straps
    • Bodycon silhouette
    • Mini-length hem
    • Textured fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4860

    Category Name: Vacation Looks

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Cutie Flower Drop Earrings

    Create the cutest everyday look with these adorable flower drop earrings! They feature a fish hook design connected to a thin metal flower-shaped outline. Style with a floral dress and strappy sandals for a pretty vibe.

    Fit & Features

    • Fish hook design
    • Thin metal flower-shaped outline


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

    Style Number/Barcode: 07001-1471

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • A Boost Of Cute Two Pack Flower Clips

    Every outfit could use a boost of these cute flower hair clips! They feature double-sided flower designs with a claw clip closure. Complete the look with a trendy shoulder bag.

    Fit & Features 

    • Two pack hair clip set
    • Double-sided flower designs
    • Claw clip closure

    Style Number/Barcode: 07006-0375

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Got The Edgy Look Oversized Sunglasses

    Get an edgy look to shade your eyes from the rays in these oversized sunglasses featuring a flat top design, tortoise plastic frames, and tinted lenses. Complete the look in a cool faux leather jacket.

    Fit & Features

    • Oversized design
    • Flat top
    • Tortoise plastic frames
    • Tinted lenses

    Style Number/Barcode: 07008-0990

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Flair Lace-Up Sandals

    Let festival season inspire your spring wardrobe with these on-trend sandals that bring a boho flair. They feature an open almond-shaped toe with a toe strap, a thin, asymmetric, strappy design across the foot, a thicker heel strap, a matching thin strappy design that wraps around the leg, and a flat sole. Style with a flowy midi dress and statement earrings.

    Fit & Features

    • Open almond-shaped toe, toe strap
    • Thin, asymmetric, strappy design across the foot
    • Heel strap
    • Thin strappy wrap-around design
    • Flat comfort sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1119

    Category Name: Vacation Looks

    Price: $5.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Fab Pearl Detail Crossbody Bag

    Simply fab, this quilted faux leather crossbody bag is a chic staple! It features an oval shape with a top zipper closure, faux pearl, rhinestone, and chain strap accents, and a thin chain-link shoulder strap. Style with your fave mules.

    Fit & Features

    • Oval shape
    • Top zipper closure
    • Faux pearl, rhinestone, and chain strap accents
    • Thin chain-link shoulder strap
    • Diamond quilted pattern
    • Faux leather material

    Style Number/Barcode: 07203-1189

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Glam Rhinestone Chrome Sandals

    Amp up your everyday looks with these casually glam chrome sandals! They feature a square toe, an asymmetrical strappy design with sparkly rhinestone accents, an open back for easy on-and-off styling, and a fab metallic sheen. Pair these sandals with a clear handbag.

    Fit & Features

    • Square toe
    • Asymmetrical strappy design, rhinestone embellishments
    • Open back
    • Flat sole
    • Chrome sheen
    • Faux leather cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1088

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Glam Pearl And Rhinestone Sandals

    You're always glam, even when it comes to your casual 'fits! These faux leather sandals are a perfect match for you. They feature a square toe, a dual clear strap design with faux pearl and mini rhinestone accents, and an open back for easy on-and-off styling. Pair with dainty stud earrings.

    Fit & Features

    • Square toe
    • Dual clear strap design
    • Faux pearls, mini rhinestones
    • Open back
    • Flat sole
    • Faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-1081

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Getaway Vibe Tropical Print Tie-Front Top

    This airy mesh top gives off getaway vibes with its trendy tropical print and effortless tie-front design. Style with denim shorts and sandals.

    Fit & Features

    • Sheer mesh fabric, high stretch
    • Tropical print
    • V-neckline
    • Tie-front design
    • Long bell sleeves
    • Cropped hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06202-000005

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Everyday Style Thong Sandals

    These classic thong sandals are perfect for everyday wear during the warmer months! They feature an almond-shaped toe with a thin thong strap design, a flat sole, and an open back for easy on-and-off styling. Pair these sandals with hoop earrings for a simple yet chic vibe.

    Fit & Features

    • Almond-shaped toe
    • Thin faux leather thong straps
    • Flat sole
    • Open back
    • Faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-1087

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Girl Crepe Tie-Front Top

    Show your love for floral in this crepe crop top featuring three-quarter-length kimono sleeves, a plunge V-neckline, and a tie-front closure. Complete your cute look in new denim bottoms.

    Fit & Features

    • Three-quarter-length kimono sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Cropped hem
    • Ditsy floral print
    • Crepe woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1405

    Category Name: Vacation Looks

    Price: $11.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hide Out Square Oversized Sunglasses

    When you want to be under the radar, these oversized sunglasses are perfect for keeping low-key! They feature square-tinted lenses, rubber nose supports, and trendy chain link arms. Complete the look in a casual jacket for a coffee run.

    Fit & Features

    • Oversized style
    • Square tinted lenses
    • Rubber nose supports
    • Chain link arms

    Style Number/Barcode: 07008-0982

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Bold Dragon Print Cropped Tee

    Create a trendy bold look with this printed cropped tee that slays! It features a crew neckline, short sleeves, a cropped hem, a thin strappy design that ties at the waist, and an all-over dragon print pattern. The soft brushed knit fabric offers plenty of stretch. Style with faux leather shorts and heels!

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Fitted, cropped hem
    • Thin strappy design at the waist, tie closure
    • Dragon print
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-1522

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Freshly Picked Floral Skater Dress

    Freshly picked from the garden. This floral skater dress is ready for your springtime festivities! It features short puff sleeves, a sweetheart neck with a tie-front closure, an open lace-up back design, and a tiered ruffled short-length hem. Complete the look in trendy new mules.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck, tie-front closure
    • Open lace-up back design
    • Skater silhouette
    • Tiered ruffle short-length hem
    • Watercolor floral print, non-stretch fabric, woven lining
    • Runs true to size

    Style Number/Barcode: 05102-4993

    Category Name: Vacation Looks

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Sunshine Mesh Crop Bustier

    Embrace the sunshine in this floral mesh bustier perfect for the warmer season ahead! It features a sleeveless sweetheart neck, ruched bust, tank-style straps, a low square-cut back, and a cropped hem. Complete the look in a flirty mini skirt for a day date!

    Fit & Features

    • Sleeveless sweetheart neck, tank-style straps
    • Ruched bust
    • Low square-cut back, zipper and hook-eye closure
    • Cropped hem
    • Floral print mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4589

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Everyday Sparkle Rhinestone Strappy Sandals

    Add some sparkle to your everyday look with these trendy-glam sandals. They feature an open almond toe, an asymmetric strappy design with mini rhinestone embellishments, an adjustable ankle strap, and a low block heel. Style with a cute handbag.

    Fit & Features

    • Open almond toe
    • Asymmetric strappy design, mini rhinestones
    • Adjustable ankle strap, buckle detail
    • Low block heel
    • Faux leather material
    • Cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1077

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Western Vibes Double Buckle Belt

    This festival season, show off chic western vibes when you accessorize your 'fits with this trendy belt! It features an adjustable double buckle design with etched detailing. Style with cowboy boots.

    Fit & Features

    • Adjustable metal double buckle design
    • Etched detailing
    • Faux leather material

    Style Number/Barcode: 07301-0604

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Grecian Mystique Bejeweled Flat Sandals

    Unlock a Grecian mystique allure in these flat patent sandals for your next getaway! They feature an almond toe, PVC clear caged straps with statement rhinestone jewels, and an adjustable ankle chain with lobster clasp closure. Complete the look in a chic sundress for a sunset dinner.

    Fit & Features

    • Almond toe
    • PVC clear caged straps
    • Statement rhinestone jewels
    • Adjustable ankle chain with lobster clasp closure
    • Patent leather footbed
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1123

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ethereal Glam Hair Claw Clip Set

    Enchant with an ethereal glam look with these stunning hair claw clips! The set features two clips, including one curved design with dainty chains and faux pearl beads, and one butterfly design with cascading snake chains and butterfly-shaped accents. Style with rhinestone stud earrings.

    Fit & Features

    • Two-pack metal claw clip set
    • Curved design, dainty chains and faux pearl beads
    • Butterfly design, snake chains and butterfly accents

    Style Number/Barcode: 07006-0394

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Full Bloom Floral Mesh Duster

    Layer on this fresh blooming floral mesh duster for a classic springtime look! It features long fitted sleeves, an open front, a long-length hem with a relaxed fit, and a beautiful floral print pattern. The sheer mesh fabric offers plenty of stretch. Style with a basic bodysuit and light wash denim.

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Long-length hem, relaxed fit
    • Floral print
    • Sheer mesh fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06202-0375

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dinner And Drinks Halter Ruffle Romper

    Create sultry flair in this halter ruffle romper for your next date night or GNO! This romper is designed to show off with a plunge halter neckline and a short ruffled hem.

    Fit & Features

    • Smooth knit stretchy fabric
    • Plunge halter neckline with button closures
    • Partial open back
    • Ruffled short-length hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-1279

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Bow Linen Strapless Mini Dress

    Look like a gift of fashion in this perfect bow linen dress for a chic wedding reception or party look! Featuring a strapless neckline with non-slip grip lining, a center front bow, a bodycon silhouette, and a flirty hem slit. Complete the look with cute block heels.

    Fit & Features

    • Strapless neckline, non-slip grip lining
    • Center front bow
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Mini-length hem with slit accent
    • Double-lined linen fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2419

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeper Of My Heart Rhinestone Three Ring Set

    You're the keeper of your heart! Flaunt your love for glamour with this three-pack ring set featuring one statement rhinestone heart ring, one heart outline ring, and one metal bead heart ring with dainty rhinestone embellishments. Style with an oversized blazer to complete your chic look!

    Fit & Features

    • Three-pack ring set
    • One statement heart rhinestone ring
    • One heart outline ring
    • One metal bead heart ring, dainty rhinestone embellishments

    Style Number/Barcode: 07004-0325

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale