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.

  • Daydreamer Tie-Dye Ruffled Chiffon Mini Dress

    Your daydreams will come true in this stunning tie-dye chiffon mini dress. It features a sleeveless V-neckline with a ruffled overlay, adjustable spaghetti straps, an elasticized high waist seam with a cute tie-front belt to highlight your waist, a ruffled and tiered short silhouette, and a flowy A-line fit. The sheer airy chiffon fabric features a pretty watercolor-like tie-dye pattern and includes a woven lining. Pair with clear heels for weekend brunches or day dates!

    Fit & Features

    • Sleeveless V-neckline, ruffled overlay
    • Adjustable spaghetti straps
    • Elasticized high waist seam, tie-front belt
    • Ruffled and tiered short silhouette, A-line fit
    • Watercolor-like tie-dye pattern
    • Sheer chiffon fabric, full woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5329

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Affection Ruched Crop Bustier

    Watch everyone give you sweet affection for looking so stunning in this mesh crop bustier perfect for styling with your favorite denim! It features a sleeveless sweetheart neck with front lattice straps, adjustable spaghetti straps, a ruched built-in padded bust with underwire, a sheer bodice with flexible boning, and back hook-eye closures. Complete the look in flare jeans.

    Fit & Features

    • Sleeveless sweetheart neck, lattice straps
    • Adjustable spaghetti straps
    • Ruched built-in padded bust with underwire
    • Sheer bodice, flexible boning, cropped hem
    • Back hook-eye closures
    • Partially lined mesh fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06001-4876

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Trendy Style Denim Mini Skirt

    This adorable denim mini skirt is perfect for the babe who loves a casual trendy style. It features a high-rise waist, large front and back pockets, side strap accents with buckle detailing, and a mini-length hem with a form-fitting silhouette. The cotton-blend denim fabric has a rigid fit with no stretch. Pair with a basic crop top and sneakers.

    Fit & Features

    • High-rise waist, belt loops
    • Hidden front zipper, button closure
    • Dual large front and back pockets
    • Side strap accents, metal buckle details
    • Mini-length hem, form-fitting silhouette
    • Cotton-blend denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06601-0078

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Greek Key On Fleek Mesh Tie-Front Top

    Look on fleek for vacationing in Greece or on a private yacht in this fab mesh Greek key print crop top! It features bell long sleeves, a V-neckline, and a tie-front closure. Style with the matching bottoms over your swimsuit for a complete look!

    Fit & Features

    • Bell long sleeves
    • V-neckline
    • Tie-front closure
    • Cropped hem
    • Greek key print
    • Sheer mesh fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06202-0319

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine Beauty Floral Ruffled Short Dress

    This adorable floral ruffled short dress was made for sunny summer days! It features a sleeveless square neckline, adjustable spaghetti straps that lead to a cross-back design, a flowy relaxed A-line silhouette, and a drop waist seam with a ruffled short-length hem. The dress showcases a dainty floral embroidered pattern on the lightweight cotton fabric. Style with espadrille sandals for a day party!

    Fit & Features

    • Sleeveless square neckline, elasticized back hem
    • Adjustable spaghetti straps, cross-back design
    • Flowy A-line silhouette
    • Drop waist seam, ruffled short-length hem
    • Dainty floral embroidered pattern
    • Cotton fabric, full woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5322

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Summer Days Ruffled Cotton Skater Dress

    Capture the perfect casual-chic summer vibe with this lightweight ruffled cotton skater dress. It features a pleated V-neckline with a ruffled collar and a tie-front design, short puff sleeves with ruffled hems, sheer crochet inserts down the bodice and along the skirt, a stretchy smocked high waist, a short ruffled and tiered skater skirt with a layered design, and a flattering fit and flare silhouette. The cotton fabric includes a woven skirt lining. Style with strappy mules.

    Fit & Features

    • Pleated V-neckline, ruffled collar, tie-front design, tassel accents
    • Short puff sleeves, elastic cinched ruffled hems
    • Sheer crochet inserts down the bodice and along the skirt
    • Stretchy smocked high waist
    • Short ruffled and tiered skater skirt, layered design, fit and flare silhouette
    • Cotton fabric, woven skirt lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5324

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Set The Curve Square Neck Maxi Dress

    Set the tone for flaunting your curves in this essential maxi dress perfect for day or night styling! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a sexy center-back high slit on double-lined knit fabric with a buttery soft feel. Complete the look with a crop denim jacket and sandals for a sunset dinner date!

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Bodycon silhouette
    • Center back high slit
    • Maxi-length hem
    • Double-lined knit fabric
    • Buttery soft and stretchy
    • Runs true to size

    Style Number/Barcode: 05102-5200

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Playful In Knit Halter Midi Sweater Dress

    Feeling playful? Turn up the charm in this sleeveless sweater midi dress perfect for family parties or baby showers! It features a halter neckline, skin-baring cutout sides and back, and a form-hugging fit on stretchy rib knit fabric with contrast trim. Complete the look in block heel mules.

    Fit & Features

    • Sleeveless halter neckline
    • Cutout sides and back
    • Form-hugging fit
    • Midi-length hem
    • Stretchy sweater rib knit fabric
    • Contrast trim
    • Runs true to size

    Style Number/Barcode: 06005-1697

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachy And Boho Crochet Bustier Tank Top

    Make beachy and boho your summer vibe with this adorable crochet knit bustier tank top! It features a sleeveless V-neckline, tank shoulder straps, a bustier-style bodice with sheer crochet inserts at the front, and a fitted, angled, and cropped hem. Style with high-rise denim shorts.

    Fit & Features

    • Sleevleess V-neckline
    • Tank shoulder straps
    • Bustier-style bodice, sheer crochet inserts
    • Back zipper closure
    • Fitted, angled, cropped hem
    • Crochet knit fabric, partial lining
    • Runs true to size

    Style Number/Barcode: 06005-1703

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take It Away Linen Strapless Ruffled Romper

    Look good on the go in this linen-blend strapless romper for vacation or fun weekend plans! It features a strapless tier ruffled neckline with non-slip grip lining, hidden side pockets, a slim curve-hugging silhouette, and a short-length hem. Complete the look in trendy sunglasses and sandals.

    Fit & Features

    • Strapless tier ruffled neckline, non-slip grip lining
    • Back zipper and hook-eye closure
    • Slim curve-hugging silhouette
    • Hidden side pockets
    • Short-length hem
    • Linen-blend fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0233

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Weekend Date Striped Midi Sweater Dress

    This on-trend striped midi sweater dress is perfect for casual weekend dates this season! It features a strapless straight across neckline with an elasticized hem, a striped color block design down the silhouette of the dress with crochet accents in the knit fabric, a midi-length hem, and a curve-hugging fit. The ribbed knit fabric offers plenty of stretch. Style with strappy sandals.

    Fit & Features

    • Strapless straight across neckline, elasticized hem
    • Striped color block design, crochet accents
    • Midi-length hem
    • Curve-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1657

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blissfully Beautiful Ditsy Floral Mini Dress

    Embrace the summer season looking blissfully beautiful in this adorable ditsy floral mini dress! It features a sleeveless round neckline with an adjustable tie-front design, a ruched bust with a small front cutout, spaghetti straps, a mini-length hem with a short front slit, and a slim-fit A-line silhouette. The ditsy floral printed knit fabric has a lightweight feel and offers plenty of stretch. Style with espadrille sandals for a weekend outing.

    Fit & Features

    • Sleeveless round neckline, adjustable tie-front design
    • Ruched bust, small front cutout, spaghetti straps
    • Mini-length hem, short front slit
    • Slim-fit A-line silhouette
    • Ditsy floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5313

    Category Name: Vacation Looks

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready, Set, Slay V-Waist Denim Mini Skirt

    Ready to slay? Cause this denim mini skirt is your perfect pairing for trending all season! It features a mid-rise V-waist cut, a back zipper and hook and eye closure, and a bodycon silhouette. Complete the look with matching jacket.

    Shop Matching Jacket: Ready, Set, Slay Wrap Crop Denim Jacket

    Fit & Features

    • Mid-rise, V-waist cut
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Mini-length hem
    • Medium-wash denim fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06601-0081

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Breeze Ruffled Cotton Skater Dress

    Capture an iconic summer look perfect for day parties in this breezy ruffled cotton skater dress! It features a crew neckline, adorable short puff sleeves, a small back keyhole cutout, a stretchy smocked high waist, a short ruffled and tiered skater skirt with pleated detailing, and a flattering fit and flare silhouette. The lightweight cotton fabric includes a woven skirt lining. Style with strappy sandals.

    Fit & Features

    • Crew neckline, short puff sleeves, elastic cinched hems
    • Small back keyhole cutout, button closure
    • Stretchy smocked high waist
    • Short ruffled and tiered skater skirt, pleating
    • Fit and flare silhouette
    • Cotton fabric, woven skirt lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5323

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Sway Ruffled Tiered Short Dress

    Keep your daytime look sweet in this lightweight woven short dress perfect for stylishly swaying to your summer playlist! It features a V-neck and back, a wrap-front design with a dainty crochet trim, tie-back spaghetti straps, short sleeves with ruffled trims, a sheer crochet trim waist, a short-length hem with an adorable ruffled and tiered silhouette, and a flowy A-line fit. The gauze fabric includes a partial woven lining. Pair with strappy sandals.

    Fit & Features

    • V-neck and back, wrap-front design, tie-back straps, metal beaded accents
    • Short sleeves, ruffled trims
    • Sheer crochet waist and trim
    • Hidden back zipper, hook and eye closure
    • Short-length hem, ruffled and tiered silhouette, A-line fit
    • Gauze fabric, partial woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-5321

    Category Name: Vacation Looks

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Staple Tie-Front Midi Dress

    This trendy tie-front midi dress is a stylish summer staple! It features a sleeveless V-neckline, a tie-front design at the bust with a small keyhole cutout, spaghetti straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Pair with espadrille sandals for happy hour.

    Fit & Features

    • Sleeveless V-neckline
    • Tie-front design, small keyhole cutout
    • Spaghetti straps
    • Midi-length hem
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5250

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Beauty Abstract Cutout Maxi Dress

    Embrace your vacation looking like beauty in this abstract print maxi dress destined for sunset dinners and cocktails by the pool! It features a sleeveless square neck, sleek bungee spaghetti straps, a sassy cutout waist with a hoop insert, a slim form-hugging silhouette, and a high front slit on lined smooth knit and stretchy fabric. Complete the look in cute sandals and earrings.

    Fit & Features

    • Sleeveless square neck
    • Bungee spaghetti straps
    • Cutout waist, hoop insert
    • Slim form-hugging silhouette
    • High front slit, maxi-length hem
    • Abstract print, smooth knit fabric, short knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5101

    Category Name: Vacation Looks

    Price: $5.97 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Basic Crew Neck Tank Mini Dress

    A sweet basic mini dress for all your styling needs this season! It features a sleeveless crew neckline, a bodycon silhouette, and a mini-length fitted hem on smooth and stretchy knit fabric. Complete the look with trendy sunglasses and sandals for a trip to the farmer's market!

    Fit & Features

    • Sleeveless crew neckline
    • Bodycon silhouette
    • Mini-length fitted hem
    • Smooth and stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5079

    Category Name: Vacation Looks

    Price: $5.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elite Summer Style Marble Print Maxi Dress

    Show off an elite summer style in this eye-catching marble print maxi dress! It features a sleeveless scoop neckline, spaghetti straps, an alluring lower back cutout, a maxi-length hem with a thigh-high side slit to showcase some leg, and a bodycon silhouette that will hug your curves. The stretchy knit fabric features a trendy multi-colored marble print pattern. Complete the look with strappy heels for sunset happy hour. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps, lower back cutout
    • Maxi-length hem, high side slit
    • Bodycon silhouette
    • Multi-colored marble print
    • Slinky knit fabric, short knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5261

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sergeant Of Style Cargo Pocket Mini Dress

    Elevate your status to sergeant of style in this edgy mini dress perfect for casual plans! Featuring a sleeveless square neckline, adjustable spaghetti straps, a lightly padded bust, an underbust seam, cargo-style flap side pockets, and a short bodycon silhouette. Style with strappy clear strap heels.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Lightly padded bust, underbust seam
    • Back zipper and hook-eye closure
    • Bodycon silhouette, mini-length hem
    • Twill woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5104

    Category Name: Vacation Looks

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Perfection Striped Tank Mini Dress

    This adorable striped tank mini dress is the perfect casual style for a subtly elevated look! It features a sleeveless crew neckline, tank shoulder straps, a mini-length subtle curved hem, and a bodycon silhouette that offers a form-hugging fit. The striped ribbed knit fabric has plenty of stretch. Pair with strappy sandals.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Mini-length subtle curved hem
    • Bodycon silhouette
    • Striped print
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5102

    Category Name: Vacation Looks

    Price: $19.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ethereal Glamour Butterfly Fringe Rhinestone Headband

    Give off an aura of ethereal glamour with this gorgeous embellished headband! It features a thin flexible metal design with mini rhinestone embellishments and long cascading fringe on each side with rhinestones, dainty chains, and detailed butterfly accents. Style with simple stud earrings.

    Fit & Features

    • Thin flexible metal headband
    • Two rows of mini rhinestone embellishments
    • Three rows of dangling fringe on each side
    • Mini rhinestones, dainty chains, butterfly accents

    Style Number/Barcode: 07006-0404

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevate Everyday V-Neck Tank Crop Top

    Elevate every outfit with this basic tank top perfect for dressing up, down, or layering! It features a sleeveless V-neckline, wide shoulder straps, and a fitted crop hem on stretchy rib knit fabric. Complete the look in a trendy mini skirt and earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Wide shoulder straps
    • Fitted crop hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1637

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Abstract Chic Twist-Front Crop Top

    Showcase your artsy side in this abstract chic twist-front crop top! It features a sleeveless V-neck and back design, tank shoulder straps, a twist-front design at the bust, a fitted cropped hem, and an all-over multi-colored swirl print pattern. Style with the matching straight-leg pants for a bold allure.

    Shop Matching Bottoms: Abstract Chic Straight-Leg Pants

    Fit & Features

    • Sleeveless V-neck and back
    • Tank shoulder straps
    • Twist-front design at the bust
    • Fitted cropped hem
    • Multi-colored abstract swirl print
    • Knit slink fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4894

    Category Name: Vacation Looks

    Price: $4.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale