Vacation Dresses & Outfits

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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.

  • Match My Energy Three-Pack Hoop Earrings

    This three-pack of hoop earrings keeps up with the trends! This pack includes a pair of simple hoop earrings, glittering rhinestone hoop earrings, and intricately etched hoop earrings, perfect for any occasion. Complete the look in a bodycon dress for dinner and drinks!

    Fit & Features

    • Three-pack hoop earrings
    • One pair of simple hoop earrings, post-back closure
    • One pair of rhinestone hoop earrings, post-back closure
    • One pair of etched hoop earrings, omega closure

     

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

    Style Number/Barcode: 07001-1983

    Category Name: Vacation Dresses & Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

  • Sunny Chic Halter Ruched Crochet Crop Top

    Create a sunny chic 'fit with the cutest crochet crop top! Designed with a breezy sheer crochet knit fabric with a partial lining, this top was made for summer getaways. It features a sleeveless halter neckline with a racerback design, and a small keyhole cutout at the back with beaded tie-back straps for a customized fit. The front features ruching with adjustable drawstring beaded straps and a fitted cropped hem for a snatched silhouette. Complete your look with the matching maxi skirt and a pair of slip-on sandals!

    Shop Matching Bottoms: Sunny Chic High Slit Crochet Maxi Skirt

    Fit & Features

    • Sheer crochet knit fabric, partial knit lining
    • Halter neckline, racerback design
    • Back keyhole cutout, tie-back straps
    • Ruched front with adjustable drawstring straps
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2251

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • More Than Sweet Tie Strap Fit-And-Flare Dress

    Who can imagine a look sweeter than this fit-and-flare dress? Showcase your darling side in this short eyelet dress at casual brunches or parties! This charming dress features a square neckline, tie shoulder straps, and a flattering fit-and-flare silhouette. With a tiered ruffled short-length hem and delicate eyelet lace fabric, this dress will have you looking and feeling your best. Complete the look in trendy sneakers for a cute style!

    Fit & Features

    • Sheer eyelet lace fabric with knit lining, moderate stretch
    • Square neckline
    • Tie shoulder straps
    • Fit-and-flare silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5532

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Charm Halter A-Line Midi Dress

    Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Woven fabric, no stretch
    • Halter pleated neckline
    • Open back, zipper and hook-eye closure
    • Beaded tie waist
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5648

    Category Name: Vacation Dresses & Outfits

    Price: $30.00 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Boho Layered Beaded Chain Charm Necklace

    The charm necklace features a four-row design with a sleek snake chain layer, a dainty beaded chain layer, a trendy flat chain layer, and a thin cord layer accented with beading and an oval-shaped metal pendant. Style with hoop earrings.

    Fit & Features

    • Four-row layered necklace
    • Snake chain
    • Dainty beaded chain
    • Flat chain
    • Beaded cord with oval pendant
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1878

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Allure Abstract Print Satin Crop Top

    Bring the allure to your summer 'fits with this abstract print satin crop top! Designed with a silky satin woven fabric with a trendy abstract pattern, this top features a sleeveless V-neckline, halter spaghetti straps with a tie-back design, a bold open back with an elasticized back strap for added stretch, and a cropped hanky-style hem with a form-hugging fit. Pair with denim shorts and sandals!

    Fit & Features

    • Abstract print
    • Satin woven fabric, knit bust lining
    • V-neckline
    • Halter tie-back spaghetti straps
    • Open back, elasticized back strap
    • Cropped hanky hem, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06003-2587

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Me Pretty Satin Abstract Wide-Leg Pants

    Color you pretty in these satin pants to brighten up this new season! They feature a flattering high-rise waist, an elasticized back band, front pleating, and a wide-leg silhouette on smooth satin with an abstract print. Complete the look with the matching top for a vacation!

    Shop Matching Top: Color Me Pretty Satin Abstract Crop Top

    Fit & Features

    • High-rise waist, elasticized back band
    • Front pleating
    • Wide-leg silhouette
    • Abstract print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1371

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

  • Garden Of Roses Chiffon Midi Dress

    Frolic through the garden or your next soiree in this rose print chiffon midi dress! It features a sleeveless sweetheart neck, spaghetti straps, a ruched bust with a tie, and a slim A-line silhouette with a flirty front slit. Complete the look in strappy block heels.

    Fit & Features

    • Sleeveless sweetheart neck, spaghetti straps
    • Ruched bust with tie
    • Back zipper and hook-eye closure
    • Slim A-line silhouette
    • Front slit, midi-length hem
    • Rose print, airy chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2081

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylishly Striped Knit Off-The-Shoulder Mini Dress

    This trendy striped knit mini dress is designed with a chic off-the-shoulder straight neckline with a flattering fold-over design and a bodycon silhouette to show off your curves. Pair with sneakers for a cute everyday look.

    Fit & Features

    • Striped ribbed knit fabric, plenty of stretch
    • Off-the-shoulder straight neckline, fold-over design
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5853

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Truly Radiant V-Neck Lace Bodycon Mini Dress

    This sleeveless lace mini dress features a flattering ruffle trim V-neckline, spaghetti straps, and a bodycon silhouette perfect for a date or brunch.

    Fit & Features

    • Lace-lined fabric
    • Ruffle trim V-neckline
    • Spaghetti straps
    • Bodycon mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3534

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Daring Texture Knit Crop Top

    Feel daringly stylish with this crop top! This ultra-trendy top features a sleeveless V-neckline, bungee spaghetti straps, an alluring open back with a strappy design, and a vivid V-cut cropped hem on sheer texture knit fabric. Dare to stand out and shop the matching bottoms to complete the look!

    Shop Matching Bottoms: Feeling Daring Texture Knit Mini Skirt

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Open back, strappy design, tie closure
    • V-cut cropped hem
    • Sheer texture knit fabric, lined bust
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-5214

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • To Be Adored Scoop Neck Floral Lace Mini Dress

    You're certain to be adored in this floral lace mini dress wherever you go! The scoop neckline with a bust tie adds a touch of feminine charm while the adjustable spaghetti straps provide a perfect fit. Its bodycon silhouette and mini-length hem accentuate your curves, making you feel confident and stylish. Complete the look with a mini handbag.

    Fit & Features

    • Ditsy floral print, lace fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Scoop neckline with bust tie
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5717

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Muse Watercolor Chiffon Flowy Midi Dress

    You'll be a dreamy muse in this gorgeous watercolor chiffon flowy midi dress! The airy lined chiffon fabric is detailed with a mesmerizing watercolor print for the perf summertime vibe. The mid-length dress features a sleeveless halter neckline with a center stone accent, tie-back spaghetti straps, a partially open back for a touch of allure, and a lower-smocked back design for added stretch. The fitted high waist flows out to a gorgeous A-line silhouette with an asymmetrical hemline for beautiful movement. Style this long dress with espadrille wedges.

    Fit & Features

    • Watercolor print
    • Sheer chiffon fabric with smooth woven lining
    • Halter neckline, stone detail, tie-back straps
    • Partial open back, lower stretchy smocked back
    • Flowy A-line silhouette
    • Asymmetrical hemline
    • Runs true to size

    Style Number/Barcode: 05101-3306

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Neutrals Halter Strappy Tropical Midi Dress

    Unveil this chic tropical midi dress on the island! The cowl halter neckline and strappy open back add a touch of allure, while the bodycon silhouette and asymmetrical cut hem flatter your figure. Complete the look with cute block heel sandals and sunglasses!

    Fit & Features

    • Tropical print, smooth knit stretchy fabric
    • Halter cowl neckline, spaghetti strap
    • Strappy open back
    • Bodycon fit
    • Asymmetrical cut hem
    • Runs true to size

    Style Number/Barcode: 05102-5185

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Tropics Halter Lace Tropical Mini Dress

    Hit the tropics in this stylishly sultry tropical mini dress perfect for dinner and cocktails! Crafted from a tropical patterned lace fabric, this mini-length dress features a halter neckline with tie closure and a stunning bodycon silhouette to show off your curves. Complete the look in sandals and earrings!

    Fit & Features

    • Tropical patterned lace fabric, stretchy knit lining
    • Halter neckline, tie closure
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5796

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Girls Are Girling Trucker Hat

    Keep it cute and sassy in this trucker hat that says it all! It features a classic curved brim, an embroidered script that reads "The Girls Are Girling" and a mesh back with an adjustable strap. Complete with denim shorts. 

    Fit & Features

    • Curved brim
    • Embroidered script reads "The Girls Are Girling"
    • Mesh back with adjustable closure 

    Style Number/Barcode: 07302-1667

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

  • Fun And Games Tie Strap Bodycon Floral Mini Dress

    This floral mini dress is here for fun and games this summer! Perfect for casual weekend fun, this dress features spaghetti strap ties, a sweetheart neckline, and all-over ruched seams that accentuate your curves along the bodycon fit. Complete the look with a trendy purse.

    Fit & Features

    • Floral ditsy print, brushed knit fabric
    • Spaghetti strap ties
    • Sweetheart neckline
    • Ruched bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5728

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Off Your Glow Tropical Lace-Up Midi Dress

    Show off your vacation glow in this tropical midi dress all over the island or resort! With a square neckline, spaghetti straps, and a lace-up back, this side slit dress hugs your body in all the right places with side ruched seams and a bodycon fit. Complete the look in sandals.

    Fit & Features

    • Tropical print, mesh fabric, sewn-in knit lining, moderate stretch
    • Spaghetti straps
    • Square neckline
    • Lace-up back
    • Ruched side seams, bodycon fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5866

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Serving Vibes Cutout Geometric Mesh Maxi Dress

    Serve major vibes in this geometric mesh maxi dress out by the beach this weekend or for a getaway! The square neckline, adjustable spaghetti straps, and form-hugging fit show off your curves while the cutout sides and back add a touch of sass. Complete with a center-back slit and maxi-length hem for effortless movement. Style this sleeveless dress with earrings and sandals.

    Fit & Features

    • Geometric print, mesh fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Square neckline
    • Cutout sides and back
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5759

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachy Glam Rhinestone Palm Tree Metallic Sandals

    Level up your fabulous vacay 'fits with these glam rhinestone metallic sandals! Made with sleek faux leather with a metallic sheen, they feature a square-shaped toe, a thong strap with a glitzy rhinestone-embellished palm tree design, an adjustable ankle strap with a buckle closure, and a flat sole for comfortable wear. Style with a flowy sundress and hoop earrings for a beachside dinner!

    Fit & Features

    • Faux leather upper, metallic sheen
    • Square toe
    • Thong strap
    • Rhinestone-embellished palm tree design
    • Adjustable ankle strap with buckle closure
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1229

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Charm Lace-Up Babydoll Crop Top

    You'll radiate sweet charm in this babydoll crop top all season! With delicate spaghetti straps and a V-neckline, this top boasts a stretchy smocked bust that hugs your curves for a flattering fit. The lace-up back adds a touch of allure, while the ruffled cropped hem adds a playful touch. Complete the look in a denim skirt and block heels for any occasion!

    Fit & Features

    • Gauze woven fabric, no stretch
    • V-neckline
    • Stretchy smocked bust
    • Spagehtti straps, lace-up back
    • Babydoll silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 06003-2524

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Refreshing Charm Smocked Striped A-Line Mini Dress

    This sleeveless striped mini dress features a flattering square neckline and a smocked A-line silhouette with a trendy drop waist seam. The ruffled hem adds a flirty touch perfect for picnics or a day at the beach. 

    Fit & Features

    • Striped woven fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Smocked A-line silhouette
    • Drop waist seam
    • Mini-length ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5826

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Life Beaded Straw Cowboy Hat

    A straw cowboy hat featuring a distressed wide brim with a beaded string trim and a snug fit. Style with cowboy boots.

    Fit & Features

    • Distressed wide brim
    • Beaded string trim
    • Snug fit
    • Straw material

    Style Number/Barcode: 07302-1702

    Category Name: Vacation Dresses & Outfits

    Price: $4.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Cutie Halter Cutout Striped Linen Jumpsuit

    Hit the coast in this breezy cute striped linen jumpsuit! This playful piece features a halter neckline with a spaghetti strap tie and a cutout bodice to flaunt some skin. The stretchy smocked back and wide-leg silhouette provide comfort and style, while the striped print adds a pop of personality to the linen-blend fabric. Complete the look in platform sandals.

    Fit & Features

    • Striped print, linen blend fabric
    • Halter neckline, spaghetti strap tie
    • Cutout bodice
    • Back zipper and hook-eye closure, stretchy smocking
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0817

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale