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.

  • Dainty Chic Shine Layered Star Charm Necklace

    Show off a dainty chic shine with this layered star charm necklace. It features a shorter layer with a beaded chain design and a longer layer with a center star charm with a gemstone accent. Style with your fave hoop earrings.

    Fit & Features

    • Premium silver-dipped or gold-dipped necklace
    • Two-row layered design
    • Shorter layer, beaded chain design
    • Longer layer, center star charm, gemstone accent
    • Lobster clasp closure

    Style Number/Barcode: 07002-1513

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Slay Ribbed Knit Midi Dress

    Showcase an everyday slay in this curve-hugging midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a double strap design, a midi-length hem with a bodycon silhouette, and a thigh-high side slit for a sultry accent. The ribbed knit fabric offers plenty of stretch. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, double strap design, tie closure
    • Midi-length hem, bodycon silhouette
    • High side slit
    • Ribbed knit fabric, lining at the bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4770

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Sunshine Linen Tie-Back Midi Dress

    For the sun-soaked days ahead, this linen midi dress will make a cute companion! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back closure, and a flowy ruffled hem. Style with trendy sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Tie-back closure
    • Flowy ruffled midi hem
    • Airy linen fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5012

    Category Name: Vacation Looks

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • She's A Doll Sweetheart Skater Dress

    You'll be looking like a total doll in this poplin skater mini dress for graduation and family parties! The dress features adorable puff short sleeves, a sweetheart neckline, an empire waist seam, and a flattering fit and flare short-length silhouette. Complete the look in eye-catching lace-up heels.

    Fit & Features

    • Puff short sleeves, sweetheart neckline
    • Back zipper and hook-eye closure
    • Empire waist seam
    • Fit and flare, skater silhouette
    • Short-length hem
    • Poplin cotton-blend fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2324

    Category Name: Vacation Looks

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Glam Rhinestone Oversized Sunglasses

    Level up your looks with these embellished sunglasses that bring the summer glam! They feature an oversized flat top design with two rows of mini rhinestone embellishments and reflective lenses. Complete your accessories with sleek hoop earrings.

    Fit & Features

    • Oversized flat top design
    • Two rows of mini rhinestones
    • Reflective lenses
    • Plastic frame

    Style Number/Barcode: 07008-1011

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pleated Princess Bow Back Skater Dress

    Look and feel like a princess in this skater dress for cocktail wedding showers or graduation parties! It features a sleeveless square neck, adjustable spaghetti straps, a pleated bodice with a pretty bow on the back, and a fit-and-flare short silhouette. Complete the look in stiletto mules and a clutch.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Pleated bodice, back bow, zipper closure
    • Skater, fit and flare silhouette
    • Short-length hem
    • Cotton-blend fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2333

    Category Name: Vacation Looks

    Price: $5.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Whimsical Statement Flower Earrings

    Add whimsical flair with these flower earrings, perfect for special occasions to date nights! 

    Fit & Features

    • Flower decorations
    • Fish hook

     

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

    Style Number/Barcode: 07001-000013

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Trendsetter Strappy Platform Sandals

    Show up this season with a trendy summer style in these sleek and strappy platform sandals. They feature a round toe, a dual adjustable strap design with buckle and stud details and a patent faux leather sheen, an open back for easy on-and-off styling, and an edgy platform lug sole. Pair these sandals with a graphic tee and distressed denim shorts.

    Fit & Features

    • Round toe
    • Dual adjustable strap design
    • Buckle and stud details, patent faux leather sheen
    • Open back, slip-on design
    • Platform lug sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1146

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Desert Vibes Turquoise Stone Cowboy Hat

    Elevate your desert weekend getaway looks with this chic cowboy hat. It features a structured top, a wide, curved, up-turned brim, and a sleek thin faux leather band with detailed metal accents with turquoise stone embellishments. Style with a corset top and denim shorts.

    Fit & Features

    • Structured top
    • Wide, curved, up-turned brim
    • Thin faux leather band
    • Detailed metal accents
    • Turquoise stone embellishments

    Style Number/Barcode: 07302-1470

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • '90s Babe Butterfly Hair Clip Pack

    Throw it back and get the cutest '90s babe look with this trendy butterfly hair clip pack. The set features six pairs of small butterfly clips in assorted multi-colored hues. Style with hoop earrings.

    Fit & Features

    • Small butterfly hair clips
    • Six pairs
    • Assorted multi-colored hues

    Style Number/Barcode: 07006-0401

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirtatious Mood Ruffled Knit Romper

    Style up this flirty ruffled knit romper for your summer weekend plans! It features an off-the-shoulder neckline with a dainty ruffled trim, short puff sleeves, ruching at the bust, a stretchy smocked waist, and an adorable tiered ruffled design with a short skirt layered over flowy shorts. Complete the look with beaded earrings.

    Fit & Features

    • Off-the-shoulder neckline, ruffled hem
    • Short puff sleeves, cinched hems
    • Ruched bust
    • Stretchy smocked waist
    • Tiered ruffled design, short skirt overlay, flowy shorts
    • Crepe fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06503-1059

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shorebird Crochet Woven Kimono

    Chill along the shore looking so trendy in this crochet woven kimono featuring flowy, long sleeves with cuffs and a sheer longline design. Complete the look in a crop top and denim shorts.

    Fit & Features

    • Flowy long sleeves with cuffs
    • Open-front
    • Sheer longline design
    • Crochet woven fabric

    Style Number/Barcode: 06202-0363

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's All Business V-Neck Mini Dress

    Business and babe vibes are what this woven mini dress is all about! It features a sleeveless V-neckline, wide shoulder straps, a wrap-style bust with sultry cutouts, and a form-hugging silhouette. Style with stiletto pumps and a blazer to complete the look for a cocktail event!

    Fit & Features

    • Sleeveless V-neckline, wide shoulder straps
    • Back zipper and hook-eye closure
    • Wrap-style bust, cutouts
    • Form-hugging silhouette
    • Mini-length hem
    • Woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2438

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smooth Silhouette Slit Midi Skirt

    Create the perfect basics closet by adding this smooth knit midi skirt to your lineup! It features a sleek and flattering high-rise waist, a bodycon fit, and a sultry side high slit along the midi-length hem. The double-lined stretchy knit fabric offers a seamless design and has an ultra-butterfly feel. Style with the matching top for a complete look!

    Shop Matching Top: Smooth Silhouette Crop Tube Top

    Fit & Features

    • High-rise waist
    • Bodycon fit
    • High side slit
    • Midi-length hem
    • Double-lined, butterfly soft knit fabric
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 06501-0849

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Naturally Cute Strappy Platform Wedges

    Naturally, summer calls for cute styles like this platform wedge perfect for hanging poolside or a beach day! It features a square toe, a strappy design, a platform sole, slightly cushioned footbed, and an ankle strap with buckle closure. Complete the look with a breezy kimono.

    Fit & Features

    • Square toe
    • Strappy design
    • Platform style
    • Ankle strap with buckle closure
    • Slightly cushioned footbed
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-0318

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Audience Paisley Wrap Crop Top

    Groove until sunset at the concert or party in this paisley crop top perfect summertime fun! It features retro bell long sleeves, a V-neckline, and a customizable wrap-tie hem on stretchy knit fabric. Complete the look in sleek faux leather shorts.

    Fit & Features

    • Bell long sleeves
    • V-neckline
    • Wrap-tie cropped hem
    • Paisley print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4724

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fit Check Strapless Denim Jogger Jumpsuit

    The denim jumpsuit you'll be wearing on rotation! It features a strapless elasticized neckline, hidden side pockets, a high-rise drawstring elasticized waist, and a relaxed jogger-style leg silhouette with elasticized cuffs. Complete the look in clear lucite heels and earrings for happy hour!

    Fit & Features

    • Strapless elasticized neckline
    • Hidden side pockets
    • High-rise drawstring elasticized waist
    • Relaxed, jogger-style leg silhouette
    • Elasticized cuffs
    • Light wash denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06602-0334

    Category Name: Vacation Looks

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Gem Of The Sea Faux Pearl Denim Shorts

    These statement denim shorts are truly the gem of the sea! They feature a flattering high-rise waist, front distressed accents and faux pearl embellishments, and a raw frayed cut-off hem with distressing. The jean shorts are composed of non-stretch medium wash denim with a color fade effect. Complete the look in a satin tie-front top for an haute night on the town!

    Fit & Features

    • High-rise waist
    • Front distressed and faux pearl embellishments
    • Raw frayed cut-off hem, distressing, slim, curve-hugging fit
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim fabric, no stretch, color fade effect
    • Runs true to size

    Style Number/Barcode: 06603-0326

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 70s Groove Floral Tie-Back Skater Dress

    Get into the groove of this 70s-inspired printed floral dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering skater short-length silhouette. Complete the look in rhinestone mules for a dressy date!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Skater silhouette
    • Short-length hem
    • 70s-inspired floral print
    • Woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5053

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Love For Chic Style Heart Hoop Earrings

    Show off your love for all things chic with these heart-shaped hoops. The metal earrings feature a bamboo-style texture with a click-top closure. Complete the look with a mini handbag.

    Fit & Features

    • Metal hoop earrings
    • Heart-shaped design
    • Bamboo-style texture
    • Click-top omega closure

     

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

    Style Number/Barcode: 07001-1616

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Resort Calling Mesh Tie Front Top

    Booked the trip? This top is already packed. Featuring a tie-front design, long sleeves and a dramatic crop hem, this floral mesh moment is giving vacation muse energy—made for poolside lounges or rooftop cocktails. 

    Shop The Matching Skirt: Resort Calling Mesh Slit Maxi Skirt

    Fit & Features

    • Floral print, partially lined mesh fabric
    • Long sleeves
    • Tie-front closure
    • Ultra-cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000032

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Soak Up The Sun Tropical Print Maxi Dress

    You'll be ready for those relaxing beachside strolls in this gorgeous tropical print maxi dress. It features a sleeveless V-neckline, spaghetti straps, an alluring backless design, a flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with slip-on sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Backless design, single lattice strap
    • Flowy floor-length hem, high front slit
    • Tropical palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4997

    Category Name: Vacation Looks

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smooth Silhouette Crop Tube Top

    This smooth tube top is designed to flatter and elevate every look! It features a strapless neckline, a form-hugging fit, and a sleek cropped hem. The double-lined stretchy knit fabric offers a seamless design and has an ultra-buttery feel. Style with the matching bottoms for a chic look! 

    Shop Matching Blue And Black Bottoms: Smooth Silhouette Bodycon Mini Skirt

    Shop Matching Rust Bottoms: Smooth Silhouette Slit Midi Skirt

    Fit & Features

    • Strapless neckline
    • Form-hugging fit
    • Cropped hem
    • Double-lined, buttery knit fabric
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 06002-1615

    Category Name: Vacation Looks

    Price: $11.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Me Cute Linen V-Neck Skater Dress

    Color you cute in this linen skater dress perfect for layering over your swimsuit on a beach day or pool party! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty ruffled underbust trim, and a tiered color block ruffled short-length silhouette. Style with trendy espadrille wedges.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruffled underbust trim
    • Tiered ruffle layered skater silhouette
    • Short-length hem
    • Color block pattern
    • Airy woven linen fabric, partial lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4994

    Category Name: Vacation Looks

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale