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.

  • Escape To Paradise Tropical Print Mini Skirt

    Look like you're ready to escape to paradise in this dreamy tropical print mini skirt! It features a high-rise waist, a faux wrap-front design, a mini-length hem, and a curve-hugging silhouette. The tropical palm leaf print will give off those vacay vibes. Style with the matching crop top!

    Shop Matching Top: Escape to Paradise Tropical Print Crop Top

    Fit & Features

    • High-rise waist
    • Faux wrap-front design
    • Mini-length hem, form-hugging fit
    • Tropical palm leaf print
    • Texture knit fabric, partial sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0596

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Escape to Paradise Tropical Print Crop Top

    Look like you're ready to escape to paradise in this dreamy tropical print crop top! It features a sleeveless scoop neckline, spaghetti straps, an alluring open back with a strappy cross-back lace-up design, and a fitted cropped hem. The tropical palm leaf print will give off those vacay vibes. Style with the matching mini skirt!

    Shop Matching Bottoms: Escape To Paradise Tropical Print Mini Skirt

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Open back, strappy cross-back lace-up design, tie closure
    • Fitted cropped hem
    • Tropical palm leaf print
    • Texture knit fabric, partial sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4007

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Meet My Gauze And Crochet Romper

    You see what you like, so go for it in this cute romper! It has a sleeveless V-neckline, adjustable spaghetti straps that create a cross-back design, and a fully lined lace bodice. A sheer crochet panel highlights your waist. Shorts are composed of unlined gauze fabric and offer a flowy fit. Complete the look with sandals and sunglasses for a fab day out.

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps, cross at back 
    • Sheer crochet panel at the waist
    • Flowy shorts
    • Gauze knit fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size 

    Style Number/Barcode: 06303-0217

    Category Name: Vacation Looks

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual And Chic Linen Shorts

    Stylishly elevate your weekend look with these casual and chic linen-blend shorts! They feature a high-rise waist, a button-front closure, dual front pockets, pleating, and a fitted silhouette. Complete the outfit with the matching vest and a pair of espadrille sandals for happy hour!

    Shop Matching Top: Casual And Chic Cropped Linen Vest

    Fit & Features

    • High-rise waist
    • Button-front closure, hidden front zipper
    • Dual front pockets
    • Pleating
    • Fitted silhouette
    • Linen-blend fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0212

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual And Chic Cropped Linen Vest

    Stylishly elevate your weekend look with this casual and chic linen-blend vest! It features a sleeveless V-neckline, a complete button-down front, and a fitted, cropped hem. Complete the outfit with the matching shorts and a pair of espadrille sandals for happy hour!

    Shop Matching Bottoms: Casual And Chic Linen Shorts

    Fit & Features

    • Sleeveless V-neckline
    • Button-down front
    • Dual faux pocket slits
    • Fitted, cropped hem
    • Linen-blend fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1574

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Skip A Beat Ponte V-Neck Skater Dress

    You'll be dressed to impress in this ponte skater dress as a graduate or bride-to-be! It features a sleeveless V-neckline, spaghetti straps, a flattering fit and flare silhouette, and a short-length hem. Complete the look in chic rhinestone heels.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Back zipper closure
    • Fit and flare, skater silhouette
    • Short-length hem
    • Lined ponte-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2235

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Edged Out Fringe Tie-Front Graphic Top

    Find your edge with this sassy graphic crop top perfect for festivals, concerts, and checking out a carnival! It features short sleeves, fringe trim along the shoulders, and a plunging neckline with a tie-front hem. Complete the look in a denim skort and cowboy boots!

    Fit & Features

    • Short sleeves
    • Fringe trim along the shoulders
    • Plunging neckline
    • Tie-front hem, cropped length 
    • Graphic design
    • Stretchy cotton fabric
    • Runs true to size

    Style Number/Barcode: 06002-1563

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Nights Linen High Slit Midi Skirt

    This effortlessly-chic linen midi skirt was made for summer nights! It features a high waist with a low-cut front design, a side knot detail, a midi-length hem with a sultry high slit to showcase some leg, and a flowy silhouette. The linen-blend fabric has a smooth knit lining. Style with a crop top and sandals.

    Fit & Features

    • High waist, low-cut front design
    • Side knot detail
    • Back zipper, hook and eye closure
    • Midi-length hem, high slit
    • Flowy silhouette
    • Linen-blend fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06301-0150

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Escape With Me Tropical Mini Dress

    Escape to an island getaway with this tropical mini dress perfect for a sunset dinner by the shore! It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a knotted bust accent, and a bodycon silhouette. The smooth lined knit fabric offers a moderate stretch. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Knotted bust accent
    • Bodycon silhouette, mini-length hem
    • Tropical print
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5004

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Marvel Lace-Up Mini Dress

    Everyone will marvel at you in this marble print mini dress featuring a sleeveless square neck, spaghetti straps that lace up along the back, and a bodycon silhouette. The mini-length dress is composed of a marble-printed mesh fabric with a stretch knit lining. Complete the look in platform wedges for dinner by the beach!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Mini-length hem
    • Marble print, mesh fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4990

    Category Name: Vacation Looks

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Strolls Floral Tie-Back Skater Dress

    Your stroll through the garden party will be so sweet in this floral chiffon dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a fit-and-flare skater silhouette with a short hem. Complete the look in cute sandals.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back design
    • Fit and flare, skater silhouette
    • Short-length hem
    • Watercolor floral print
    • Airy chiffon, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05102-4903

    Category Name: Vacation Looks

    Price: $9.97 $41.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Avenue Floral Crochet Skater Dress

    Stroll hand-in-hand with your lover in this floral crochet dress sure to bring the romance! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back design, a high-waist seam, and a short skater silhouette. Complete your darling look in strappy sandals.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Tie-back design, zipper and hook-eye closure
    • High waist seam, skater silhouette
    • Short-length hem
    • Floral crochet, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2396

    Category Name: Vacation Looks

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring It On Me Floral Mini Skirt

    Embrace floral vibes by adding this flirty mini skirt into your weekly lineup! The woven skirt features a classic high-rise waist, back zipper closure, a form-hugging silhouette, and a front slit accent. Complete the look in a crop top for a day at the beach!

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Form-hugging
    • Front slit accent
    • Ditsy floral print
    • Woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06301-0132

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sent With Love Swiss Dot Sleeveless Dress

    Send love from where ever you go in this swiss dot sleeveless dress whether it's a trip to Tuscany or a destination dinner with the girls! It features a sleeveless surplice V-neckline, a button-back closure with a keyhole slit detail, side ruched seams, and a bodycon silhouette with a flirty ruffled short hem. Complete the look in rhinestone mules.

    Fit & Features

    • Sleeveless surplice V-neckline
    • Button-back closure, keyhole slit detail
    • Back zipper and hook-eye closure
    • Side ruched seams, bodycon silhouette
    • Ruffled short-length hem
    • Swiss dot chiffon fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2107

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Weekend Vibes Floral Mini Dress

    Give off those effortless weekend vibes in this adorable floral mini dress! It features a V-neckline with a twist-front design, a front keyhole cutout under the bust, adjustable spaghetti straps, a smocked design down the back and body of the dress, a mini-length hem with a form-hugging silhouette, and a ditsy floral print pattern. The woven fabric offers a moderate stretch. Style with espadrille sandals.

    Fit & Features

    • Sleeveless V-neckline, twist-front design
    • Keyhole cutout under the bust, adjustable spaghetti straps
    • Smocked design down the back and body of the dress
    • Mini-length hem, form-hugging fit
    • Ditsy floral print
    • Woven fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4920

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everlasting Bliss Ditsy Floral Mini Dress

    You'll be blissful all season with this ditsy floral mini dress in your closet! Blossom into florals for spring bridal showers, graduations, and casual parties. Featuring a sleeveless square neck, adjustable spaghetti straps, and side ruched seams to accentuate your natural curves along the bodycon silhouette. Complete the look in strappy sandals.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti traps
    • Side ruched seam
    • Bodycon silhouette, mini-length hem
    • Ditsy floral print
    • Lined knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5046

    Category Name: Vacation Looks

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Challis Boho Slit Midi Skirt

    Show off some skin this spring! Create an effortless look in this casual midi skirt featuring a high-rise waist, back zipper closure, and a flirty front slit on challis boho print fabric. Complete the look in lace-up heels for a daytime outing.

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Front slit
    • Midi-length hem
    • Challis boho-inspired print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0149

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breezy Beauty Ikat Surplice Top

    Breeze in looking like beauty in this chiffon top featuring peasant long sleeves, a surplice plunge neckline, and a lower back keyhole with tie closure. Complete the look in a basic cami top and midi skirt.

    Fit & Features

    • Peasant long sleeves
    • Surplice plunge neckline
    • Lower back keyhole, tie closure
    • Ikat print
    • Sheer chiffon fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1857

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Effortless Boho Vibes Scarf Top

    Bring the effortless boho vibes with this lightweight woven scarf top. It features a sleeveless halter neckline, a completely open back with a tie-back strap design, an asymmetrical front hem, and an all-over paisley print. Style this top with high-rise mom jeans and cute sandals.

    Fit & Features

    • Sleeveless halter neckline, spaghetti straps, tie at the back of the neck
    • Open back
    • Tie-back strap design
    • Asymmetrical front hem, cropped fit
    • Paisley print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1727

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Moves Eyelet Lace Mini Dress

    The perfect sundress for bridal showers or outdoor parties! It features adorable puff short sleeves, a square neck, side ruched seams along the bodice, and a bodycon silhouette with a mini-length hem. Complete the look in trendy espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Square neck
    • Side ruched seams on bodice
    • Bodycon silhouette
    • Mini-length hem
    • Eyelet lace, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4874

    Category Name: Vacation Looks

    Price: $5.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swirl Of Attraction Printed Flare Pants

    Draw all the attraction onto you in these stylish printed flare pants at festivals or summer concerts! They feature a flattering high-rise elasticized waistband, a hip-hugging fit, and a flared hem on swirl print knit fabric. Complete the look in a cute corset top.

    Fit & Features

    • High-rise elasticized waistband
    • Hip-hugging fit
    • Flared hem
    • Swirl print
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2284

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Just Slayin' High Rise Cut Off Denim Shorts

    You'll be slayin' in these must-have denim shorts perfect for adding to your weekly rotation! They feature a flattering super high-rise waist, a form-hugging fit, and cut-off style hems with distressing on washed premium denim fabric with color fading. Complete the look in a graphic tee and sandals.

    Fit & Features

    • Super high-rise waist
    • Form-hugging fit
    • Cut off style hem, distressing
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Washed premium denim fabric, color fading, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0323

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bri High-Rise Lace-Up Flare Jeans By Windsor Denim

    Give them something to talk about when you exit the room in the Bri jeans by Windsor Denim! They feature a flattering high-rise waist with a lace-up placket, a hip-hugging fit, and a flared hem on premium denim fabric. Complete the look in a cute crop top for a concert or happy hour!

    Fit & Features

    • High-rise waist
    • Lace-up placket
    • Hip-hugging fit
    • Flared hem
    • Five-pocket styling, belt loop accents
    • Premium denim fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0403

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vineyard Gal Floral Linen Skater Dress

    Perfect for vineyard weddings, wine tasting, and daytime soirees! This vintage-inspired floral linen dress features adorable puff short sleeves, a sweetheart neck with a bust tie, a lace-up back design, and a tiered fit and flare skater silhouette with a short hem. Complete the look in on-trend espadrille wedges.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck, bust tie
    • Lace-up back design
    • Tiered fit and flare skater silhouette
    • Short-length hem
    • Vintage floral print, linen fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4919

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free