Vacation Dresses & Outfits

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STYLE SPOTLIGHT

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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.

  • Artsy Flair Strapless Cutout Abstract Mini Dress

    Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Side cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5693

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sure To Love Floral Woven Puff-Sleeve Skater Dress

    You'll love wearing this sweet floral puff-sleeve skater dress all summer long! The lightweight woven fabric is detailed with a soft floral print for a pretty feminine look. The short dress features a scoop neckline with ruching and a tie-front accent, short puff sleeves with elastic cinched hems, a stretchy smocked high waist, and an adorable fit-and-flare silhouette with a ruffled hem for a flirty vibe. Style with sneakers for a cute and casual outfit.

    Fit & Features

    • Floral print
    • Woven fabric with smooth woven lining
    • Ruched scoop neckline with tie-front detail
    • Short puff sleeves with elastic cinched hems
    • Stretchy smocked high waist
    • Fit-and-flare silhouette, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5716

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Of Romance Tie Back Rose Floral A-Line Dress

    Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.

    Fit & Features

    • Rose floral print, chiffon fabric lined with stretchy knit
    • Square neckline
    • Adjustable spaghetti straps
    • A-Line silhouette
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3257

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Signature Stripes Strapless A-Line Maxi Dress

    Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.

    Fit & Features

    • Striped pattern, cotton woven fabric, no stretch
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5802

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Aesthetic Pairing Three-Pack Bracelet Set

    Elevate any look with this three-pack bracelet set featuring a paperclip chain-link bracelet and two stretchy beaded bracelets. Complete the look with a cute crossbody bag for any occasion!

    Fit & Features

    • Three-pack bracelet set
    • One paperclip chain-link bracelet, adjustable lobster clasp closure
    • Two stretchy beaded bracelets

    Style Number/Barcode: 07003-0561

    Category Name: Vacation Dresses & Outfits

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Catch Attention Cowl Neck Abstract Floral Maxi Dress

    Catch everyone's attention in this abstract floral maxi dress at cocktail hour! The cowl neckline adds a touch of sophistication while the adjustable spaghetti straps provide a perfect fit. The form-hugging silhouette flatters your figure and the maxi-length hem offers a chic finish. Complete the look with a clutch and heels.

    Fit & Features

    • Abstract floral print, mesh fabric lined with stretchy knit
    • Cowl neckline
    • Adjustable spaghetti straps
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-3323

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fluttering Elegance Rhinestone Butterfly Earrings

    These charming earrings add a whimsical style to your look! They feature butterflies with mini rhinestone embellishments, linear chains with bar trim, and a post-back closure. Complete the look with a trendy denim jacket.

    Fit & Features

    • Butterflies with mini rhinestone embellishments
    • Linear chains with bar trim
    • Post-back closure

     

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

    Style Number/Barcode: 07001-2057

    Category Name: Vacation Dresses & Outfits

    Price: $12.90

    Availability: Out of Stock

  • Whimsical Appeal Puff Sleeve Chiffon Skater Dress

    Swiss dots add whimsical appeal to this charming chiffon skater dress perfect for birthdays, graduations, or showers! With sheer puff sleeves, a sweetheart neckline, and a tiered ruffled skater silhouette, this dress is both playful and flattering. Its short-length hem adds a touch of flirty charm. Complete the look in mules and a trendy purse!

    Fit & Features

    • Swiss dot chiffon fabric lined with stretchy knit
    • Back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-2999

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet One Off-The-Shoulder Crop Top

    Show off your sweet side in this off-the-shoulder crop top perfect for summer fun! Features a sweetheart neckline and short sleeve cuffs for a flattering fit. The adjustable drawstring allows for a customizable look and the cropped hem adds a touch of trendiness. Complete the look in denim shorts and sandals for a day out!

    Fit & Features

    • Stretchy rib knit fabric
    • Off-the-shoulder, sweetheart neckline
    • Adjustable drawstring
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06002-1865

    Category Name: Vacation Dresses & Outfits

    Price: $22.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, M, L

  • Sweet Style Bow Detail Polka Dot Mesh Mini Dress

    Show off the sweetest style on summer dates in this bow detail polka dot mini dress! Designed with an airy sheer mesh fabric with a knit lining for coverage, this mini-length dress is accented with an adorable polka dot pattern for the cutest vibe. It features a sleeveless V-neck and back design with a dainty eyelet trim, tank shoulder straps, a mini bow detail at the bust for a sweet touch, tie-back spaghetti straps, and a flirty flowy A-line silhouette. Pair with strappy mules.

    Fit & Features

    • Polka dot printed sheer mesh fabric with knit lining
    • Plenty of stretch
    • V-neck and back, tank shoulder straps
    • Mini bow detail, eyelet trim
    • Tie-back straps
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5828

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Moves Plunging Halter Bodycon Mini Dress

    Make sultry moves with all eyes on you in this sexy bodycon mini dress your next night out! The slinky knit fabric offers plenty of stretch for that perfect comfortable fit. The mini-length dress is shaped with a sleeveless plunging V-neckline with a halter strap design, an open back for even more allure, lower back ruching to accentuate your curves, and a bodycon silhouette to flaunt your gorgeous figure. Style with a rhinestone lariat necklace and stiletto heels.

    Fit & Features

    • Stretchy knit fabric, knit lining
    • Plunging V-neckline
    • Halter straps
    • Open back
    • Back ruching
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5784

    Category Name: Vacation Dresses & Outfits

    Price: $32.90

    Availability: In Stock

    Available Color: ROYAL

    Available Size: S, M, L

  • A Little Wild One-Shoulder Zebra Print Maxi Dress

    Your next night out just got a little wild in this sassy zebra print maxi dress perfect for vacation or the weekend! This form-hugging dress features a one-shoulder neckline and spaghetti strap, with a side drawstring cutout to show some skin. The high side slit and maxi-length hem add a flirty touch to this fierce and flattering piece. Complete the look with heeled sandals and earrings.

    Fit & Features

    • Zebra printed knit fabric, plenty of stretch
    • One-shoulder neckline, spaghetti strap
    • Side drawstring cutout
    • High side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5821

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Feels Off-The-Shoulder Sweater Mini Dress

    Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.

    Fit & Features

    • Sweater knit fabric, moderate stretch
    • Off-the-shoulder neckline
    • Bodycon fit
    • Mini-length
    • Runs true to size

    Style Number/Barcode: 06005-1947

    Category Name: Vacation Dresses & Outfits

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clear Obsession PVC Flat Sandals

    You'll be obsessed with these flat sandals perfect for styling on rotation! They feature an almond toe, a clear PVC strap, and a flat sole with edge trim on faux leather material. Complete the look with a trendy crossbody purse.

    Fit & Features

    • Almond toe
    • Clear PVC strap
    • Flat sole with edge trim
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1233

    Category Name: Vacation Dresses & Outfits

    Price: $12.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

  • Darling Babe Floral Woven Puff Sleeve Skater Dress

    Create a darling day date look with this floral puff sleeve skater dress! Made with a lightweight woven fabric, it is detailed with a charming dainty floral print for those sweet feminine vibes. The short dress features a V-neckline with a cute tie-front detail, short puff sleeves with a ruffled trim, a high waist seam, and a skater hem with a flirty fit-and-flare silhouette. Style with a dainty charm necklace and heels.

    Fit & Features

    • Dainty floral print
    • Woven fabric
    • V-neckline, tie-front detail
    • Short puff sleeves, ruffled trims
    • Back zipper closure, high waist seam
    • Short skater skirt, fit-and-flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3466

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Always Strapless Cutout Ruffle Maxi Dress

    Have all eyes on you in this strapless maxi dress boasting a sweetheart twist neckline and a cutout bodice. The smooth knit fabric hugs your curves along the form-hugging silhouette and creates a front center ruffle design. 

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Strapless sweetheart twist neckline
    • Cutout bodice
    • Center front ruffle design
    • Form-hugging, maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3601

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Back Strapless Strappy Mini Dress

    Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Strappy back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5767

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Blooms Floral Ruffle Chiffon Skater Dress

    Let this tropical floral skater dress bloom into your summer lineup! With a sweetheart neckline featuring delicate ruffle trim, adjustable spaghetti straps and padded bra cups, this skater silhouette will flatter your figure. The mini-length hem adds a flirty touch to this tropical floral printed chiffon dress. Complete the look with a crossbody purse and sandals!

    Fit & Features

    • Tropical floral print
    • Chiffon fabric with woven lining, no stretch
    • Sweetheart ruffle trim neckline
    • Padded bra cups
    • Adjustable spaghetti straps
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3204

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Social Butterfly Charm Necklace

    With an etched butterfly charm on a dainty chain, this necklace is a pretty piece for everyday wear. Complete the look with a stackable ring set.

    Fit & Features

    • Etched butterfly charm
    • Dainty chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-1865

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

  • Prep For Paradise Strapless Tropical Jumpsuit

    Prep yourself for paradise starting with this tropical jumpsuit to pack in your luggage! Made from a smooth knit fabric showcasing a palm tropical print, this jumpsuit features a strapless neckline with side-ruched seams that accentuate, a flattering wide-leg silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Smooth knit fabric, tropical palm print, moderate stretch
    • Strapless neckline
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2520

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Cutie Strappy Faux Leather Sandals

    Give off cutie vibes in these floral strappy faux leather sandals! They feature a round toe, an asymmetric strappy design with adorable flower accents with faux pearl center detailing, an adjustable ankle strap and heel strap, and a flat sole for comfortable wear. Style with a flowy summer dress for a perf summer look.

    Fit & Features

    • Faux leather upper
    • Round toe
    • Asymmetric strappy design
    • Flower design with faux pearl center details
    • Adjustable ankle strap, heel strap
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1213

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vibes High Slit Striped Knit Maxi Dress

    This casual-chic striped knit maxi dress is perfect for your laid-back weekend vibes! Designed with stretchy ribbed knit with a thin striped pattern, it features a sleeveless scoop neckline with spaghetti straps, high-cut side slits on each side for added movement, and a form-hugging slim fit on the maxi-length silhouette. Style this long dress with strappy sandals.

    Fit & Features

    • Striped ribbed knit fabric, short knit lining, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • High side slits
    • Slim-fit silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5778

    Category Name: Vacation Dresses & Outfits

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovely Look Cold Shoulder Bodycon Lace Mini Dress

    Nothing can compare to your lovely look in this lace mini dress as a stunning bride-to-be or birthday girlie! Featuring a trendy cold shoulder V-neckline, feminine flutter short sleeve cuffs, and delicate spaghetti straps, this dress hugs your curves for a bodycon fit that will turn heads. Complete the look with earrings and clutch.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Cold shoulder V-neckline
    • Flutter short sleeve cuffs, spaghetti straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3423

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flow My Way Chiffon Lace Trim Skater Dress

    Effortlessly flow into any occasion in this simply chic chiffon skater dress - the perfect style for bridal showers, graduates, and birthday girls! The dress features a cold shoulder V-neckline with a delicate scalloped lace trim, adjustable spaghetti straps, short-sleeve cuffs, and a flattering fit-and-flare short-length silhouette. The airy chiffon fabric includes a stretchy knit lining. Complete the look with a sleek choker and earrings.

    Fit & Features

    • Cold shoulder design, V-neckline, scalloped lace trim
    • Adjustable spaghetti straps, short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Fit-and-flare skater silhouette
    • Short-length hem
    • Airy chiffon fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2053

    Category Name: Vacation Dresses & Outfits

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale