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.

  • Go With The Flow High-Rise Wide-Leg Pants

    Flowy and effortless! These wide-leg pants are perfect for everyday styling. They feature a flattering high-rise banded waist, a wide-leg silhouette, and are designed on a textured knit fabric. Complete the look in a crop top and heels for dinner and drinks with friends!

    Fit & Features

    • High-rise banded waist
    • Wide-leg silhouette
    • Textured knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2382

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sassy Slit Strapless Midi Sweater Dress

    This comfy midi sweater dress is the perfect blend of cozy and cute! It features a trendy strapless straight-across neckline with an elastic banded hem, ensuring a secure and comfortable fit. The high front slit on the midi-length hem adds a flirty touch to your look. Its form-hugging silhouette enhances your natural curves, while the sweater knit fabric with moderate stretch keeps you snug all day. Complete your look with a pair of sandals for a fabulous and playful outfit.

    Fit & Features

    • Strapless straight-across neckline, elasticized hem
    • Midi-length hem
    • High front slit
    • Form-hugging silhouette
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1708

    Category Name: Vacation Looks

    Price: $3.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Loving Basics V-Neck Bodycon Tank Dress

    Every girl loves her basics and this sleeveless tank dress is perfect for day or night styling! It features a sleeveless notch V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look in a layered choker necklace for a backyard dinner party or casual hang!

    Fit & Features

    • Sleeveless notch V-neckline
    • Bodycon silhouette
    • Fitted mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5176

    Category Name: Vacation Looks

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shine On Me Chandelier Earrings

    Catch the light and the spotlight. These cascading chandelier earrings bring all the bold energy with a sculptural shape that turns any outfit into a moment.

    Fit & Features

    • Tiered chandelier design
    • Textured metal teardrop-shaped silhouette
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000020

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Caught In The Midi Crew Neck Tank Dress

    A midi dress you wouldn't mind being spotted in! The dress features a sleeveless crew neck, a bodycon silhouette, and a fitted midi-length hem on stretchy rib knit fabric. Complete the look in a sleek layered necklace for lunch with friends!

    Fit & Features

    • Sleeveless crew neck
    • Bodycon silhouette
    • Fitted midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5242

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Somewhere Sweet Mesh Tie Front Crop Top

    Let this mesh crop top take you somewhere sweet to show it off! The top features sheer peasant long sleeves, a plunge V-neckline, and a flirty tie-front hem. Style with sassy high-waist pants for a wine night with the girls!

    Fit & Features

    • Sheer peasant long sleeves
    • Plunge V-neckline
    • Tie-front cropped hem
    • Sheer mesh fabric
    • Runs true to size

    Style Number/Barcode: 06202-0259

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be Mine Ditsy Floral A-Line Midi Dress

    Make this ditsy floral midi dress be yours for the summer and beyond! It features a sleeveless V-neckline, adjustable spaghetti straps, a trendy tie-back cutout design, and a flattering A-line silhouette, front slit with a frayed trim, and midi-length hem. Complete the look in block heels for a dressy soiree!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back cutout design
    • Hidden side zipper closure
    • A-line silhouette, front slit, frayed trim
    • Midi-length hem
    • Ditsy floral print, airy woven fabric, short chiffon lining
    • Runs true to size

    Style Number/Barcode: 05102-5320

    Category Name: Vacation Looks

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curve-Hugging Chic Sheer Lace Maxi Dress

    Flaunt your stunning silhouette in this casual curve-hugging sheer lace maxi dress. It features a crew neckline, short sleeves, dainty ruffled trims, a maxi-length hem with a back slit accent, and a bodycon fit. The sheer textured lace fabric offers a moderate stretch. Style with clear heels.

    Fit & Features

    • Crew neckline, short sleeves
    • Back zipper and hook-eye closure
    • Ruffled trims
    • Maxi-length hem, back slit
    • Bodycon silhouette
    • Sheer textured lace fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5228

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking And Chic Marble Print Midi Dress

    So striking and chic, this marble print midi dress will capture all the attention at happy hour! It features a sleeveless V-neckline, spaghetti straps, an asymmetric high-cut midi-length hem creating a thigh-high slit, and a bodycon silhouette that will flaunt your figure. The buttery smooth and stretchy knit fabric features an all-over multicolored marble print pattern. Style with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Asymmetric high-cut midi-length hem, high slit
    • Bodycon silhouette
    • Multi-colored marble print
    • Smooth and stretchy knit fabric, full-length sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5231

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hit The Tropics V-Neck Midi Dress

    Ready for vacay babe? Hit the tropics in this perfect midi dress featuring a sleeveless V-neck, adjustable spaghetti straps, a side ruched seam, bodycon fit, and an asymmetrical side slit cutout. Complete the look in cute platform wedges.

    Fit & Features

    • Sleeveless V-neck
    • Adjustable spaghetti straps
    • Side ruched seam, bodycon fit
    • Asymmetrical midi hem, side slit cutout
    • Tropical print
    • Smooth knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4896

    Category Name: Vacation Looks

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • DO NOT ACTIVATE- Kiki, Do You Love Me Mink Lashes

    They'll be loving you in mink lashes that bring the volume! These Lurella lashes are handmade and consist of mink fibers that can elevate any makeup look!  Lashes are ultra-soft to the touch, flexible to easily mold to lids, and include a cotton thread adhesive band for easy application. Pair your glamorous lashes with a stunning chiffon romper and rhinestone heels for the perfect evening outfit. 

    Fit & Features

    • Handmade 
    • Mink fibers
    • Ultra-soft
    • Cotton thread adhesive band
    • Easy application 
    • Reusable 
    • Glue sold separately 

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07307-0013

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vibrant Getaway Abstract Midi Dress

    This abstract print midi dress was made for your next getaway! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, side ruched seams, and a flirty asymmetrical side slit along the hem. Complete the look in cute sandals.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Bodycon silhouette, side ruched seams
    • Asymmetrical side slit, midi-length hem
    • Abstract print
    • Smooth knit fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5216

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Vacay Tie-Shoulder Ruffled Short Dress

    This cute and casual ruffled short dress is perfect for a coastal summer vacay! It features a sleeveless scoop neckline, tie-shoulder tank straps, hidden side pockets, a drop waist seam with a ruffled short-length hem, and a relaxed A-line silhouette. The cotton fabric has no stretch. Style with gold hoops and espadrille sandals!

    Fit & Features

    • Sleeveless scoop neckline
    • Tie-shoulder tank straps
    • Hidden side pockets
    • Drop waist seam, ruffled short-length hem
    • Relaxed A-line silhouette
    • Cotton fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5345

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Heights Cork Platform Wedges

    Take your look to new heights with these cork platform wedges, perfect for shower celebrations, graduations, or vacay!

    Fit & Features

    • Wedge heel
    • Round toe, curved toe strap
    • Platform sole
    • Cushioned insole
    • Adjustable ankle strap, buckle closure
    • Cork and faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-0365

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Leave An Impression Abstract Midi Dress

    Leave an impression everywhere you go in this abstract midi dress! It features a sleeveless square neckline, spaghetti straps, side ruched seams to accentuate your curves, and a flattering bodycon silhouette. The dress is designed with a figure-flattering abstract print on knit fabric with a stretchy lining. Complete the look in cute sandals for a lunch date.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Abstract print, smooth knit fabric, stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5252

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Effortless Smooth Knit Bodycon Mini Dress

    Enjoy an effortless day or night out with this casual smooth knit mini dress! Its strapless neckline and bodycon silhouette are perfect for showing off those curves, while the mini-length hem ensures you get noticed! The dress is composed of a slinky smooth knit fabric with a stretchy knit lining. Complete the look in sassy lace-up sandals.

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Mini-length hem
    • Slinky smooth knit fabric, stretchy knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5289

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Glam Butterfly Statement Earrings

    Go with the glam vibes of these gorgeous butterfly statement earrings! They feature two butterfly-connected designs with etched detailing and a post-back closure. Style with a dainty layered necklace.

    Fit & Features

    • Two butterfly-connected designs
    • Etched detailing
    • Post-back closure


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

    Style Number/Barcode: 07001-1636

    Category Name: Vacation Looks

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beach Siren Energy Crochet Lace Duster

    Sunkissed, styled, and totally that girl—this crochet lace duster brings the heat wherever you go. With a flirty tie-front finished with boho-chic beads and a dreamy longline fit, it's the layer your bikini or outfit has been begging for

    Fit & Features

    • Sheer crochet lace
    • Tie-front with bead detail
    • Bell long sleeves
    • Flowy longline hem
    • Runs true to size

    Style Number/Barcode: 06202-000021

    Category Name: Vacation Looks

    Price: $42.90

    Availability: In Stock

    Available Color: TAN

    Available Size: S, M, L, XL

  • Effortless Beauty Floral Silk Scarf

    This chic silk scarf can be effortlessly styled in so many ways to add a pretty detail to your outfit. It features a multi-colored blooming floral print on the smooth silk fabric. The versatile scarf can be worn as a head wrap, a hair tie, around your neck, on your purse, and more! Complete your look with hoop earrings.

    Fit & Features

    • Silk fabric
    • Multi-colored floral print

    Style Number/Barcode: 07305-0451

    Category Name: Vacation Looks

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendsetting Cutie Cable Knit Lace-Up Dress

    Step out as a trendsetting cutie in this cable knit midi dress perfect for daytime strolls! It features a sleeveless square neck, thin shoulder straps that create the lace-up back design, a tie-waist belt, a bodycon silhouette, a side slit, and a midi-length hem. Complete the look in flat sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck, thin shoulder straps
    • Lace-up back design
    • Tie-waist belt
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Cable knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5155

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Boho Flair Straw Buckle Woven Belt

    This trendy woven belt will give your summer looks that beachy boho flair! It features a wide woven design, a large square wooden buckle with straw detailing, and an adjustable fit. Style over a flowy summer dress with espadrille sandals.

    Fit & Features

    • Wide woven design
    • Large square wooden buckle, straw detailing
    • Adjustable fit

    Style Number/Barcode: 07301-0654

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Chic Wooden Buckle Woven Belt

    Style up your summer 'fits with this trendy woven belt for a bohemian chic vibe! It features a wide woven design with a circular wooden buckle and an adjustable fit. Pair over a flowy summer dress with strappy sandals!

    Fit & Features

    • Wide woven design
    • Circular wooden buckle
    • Adjustable fit

    Style Number/Barcode: 07301-0655

    Category Name: Vacation Looks

    Price: $4.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Taking Care Of Business Collar Tank Mini Dress

    Take care of business in preppy style! This sleeveless mini dress features a trendy collared V-neckline, a bodycon silhouette, and a fitted mini-length hem on stretchy rib knit fabric. Complete the look with a dainty bracelet for a coffee shop hang!

    Fit & Features

    • Sleeveless collared V-neckline
    • Bodycon silhouette
    • Fitted mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5139

    Category Name: Vacation Looks

    Price: $13.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt With Confidence Strappy Back Midi Dress

    Blow kisses to all of your admirors as you pass by in this chic one-shoulder midi dress! It features a wide shoulder strap and an asymmetrical strappy back design, a bodycon silhouette, and a center back slit accent on stretchy ribbed knit fabric. Complete the look with a sleek bracelet and clutch. 

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Wide shoulder strap, asymmetrical strappy back design
    • Bodycon silhouette
    • Center back slit accent
    • Midi-length hem
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5054

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale