Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • 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
  • Effortlessly Ethereal Floral Mesh Maxi Dress

    Effortlessly ethereal will be your vibe in this gorgeous floral mesh maxi dress! It features a strapless straight-across neckline, a form-hugging fit at the bodice and waist, a flowy maxi-length hem, a thigh-high front slit with ruffled detailing for a chic accent, and a slim-fit silhouette. The lined sheer mesh fabric features an all-over intricate floral print pattern. Style with duster earrings and clear heels for a stunning wedding guest look!

    Fit & Features

    • Strapless straight-across neckline, elastic banded hem
    • Fitted bodice and waist
    • Flowy maxi-length hem, thigh-high front slit, ruffled accents
    • Slim-fit silhouette
    • Detailed floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-3040

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • 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
  • Show Up And Stun Geometric Print Midi Dress

    Show up and stun for casual drinks with the girls in this trendy midi dress! It features a sleeveless square neckline, spaghetti straps, a midi-length hem, a form-hugging silhouette, and a color block geometric printed pattern to catch everyone's eye. The buttery-smooth lined knit fabric offers plenty of stretch for comfortable wear. Style with clear mules!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Midi-length hem
    • Form-hugging silhouette
    • Color block geometric print
    • Smooth and stretchy knit fabric, full knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5260

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dainty Detailed Rhinestone Belly Chain

    You'll love the dainty-chic vibes of this detailed chain-link belly chain! It features oval-shaped engraved accents with mini rhinestone embellishments. Includes a back adjustable chain with a lobster clasp closure. Style with sleek hoop earrings.

    Fit & Features

    • Dainty chain-link design
    • Oval-shaped engraved accents
    • Mini rhinestone embellishments
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07002-1526

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Love Tropical Print Maxi Dress

    Fall in love with the island you're vacationing on in this breezy tropical maxi dress perfect for sunset cocktails and dinners! It features a sleeveless V-neckline, adjustable spaghetti straps, a stretchy smocked bust, and a flowy maxi-length silhouette with a flirty front slit. Complete the look in wedge sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bust
    • Flowy maxi-length hem
    • Front slit
    • Tropical palm leaf print, airy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5111

    Category Name: Vacation Looks

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Layer On The Style Sheer Chiffon Kimono

    Layer on the style with this sheer chiffon kimono perfect for styling over your sweet vacay look or beach wear! It features flowy short sleeves, an open front design, a tie-waist belt, and a flowy short-length hem. Complete the look in trendy sandals.

    Fit & Features

    • Flowy short sleeves
    • Open front design
    • Tie-waist belt
    • Flowy short-length hem
    • Sheer chiffon woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1182

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knot Your Bae V-Neck Layered Romper

    Make hearts melt when you breeze into the room in this sleeveless romper for the perf easy and cute look! It features a V-neckline, spaghetti straps, a flirty bust knot tie with a cutout accent, a fitted waist, and a layered short-length hem. The romper is composed of a lightweight woven fabric and has no stretch. Style with strappy clear heels for a party!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Front bust knot tie, cutout accent
    • Back zipper closure
    • Fitted waist, layered short-length hem
    • Lightweight woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0329

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fly By Satin Butterfly Midi Skirt

    Whimsical and sleek, this satin midi skirt will inspire you to spread your wings! It features a high-rise waist, a hip-hugging fit, and a slightly flowy hem. The skirt is composed of an abstract butterfly print on non-stretch satin fabric. Style with the matching top.

    Shop Matching Top: Fly By Satin Butterfly Crop Top

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Slightly flowy midi hem
    • Abstract butterfly print
    • Non-stretch satin fabric
    • Runs true to size

    Style Number/Barcode: 06401-0526

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fly By Satin Butterfly Crop Top

    Whimsical and sleek, this satin crop top will inspire you to spread your wings! It features peasant long sleeves, a sweetheart neck, a stretchy smocked back, and a twisted cropped hem. The top is composed of an abstract butterfly print on non-stretch satin fabric. Style with the matching bottoms.

    Shop Matching Bottoms: Fly By Satin Butterfly Midi Skirt

    Fit & Features

    • Peasant long sleeves
    • Sweetheart neck
    • Stretchy smocked back
    • Twisted cropped hem
    • Abstract butterfly print
    • Non-stretch satin fabric
    • Runs true to size

    Style Number/Barcode: 06003-2136

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free