Vacation Looks

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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.

  • Tropical Escape Smocked Tube Top
    Escape to an island paradise with this vacay-ready top! It features a straight strapless neckline, a lettuce-edge trim and a tie front accent. The tropical palm leaf print features green hues with coral hued florals. Top is composed of stretchy smoked fabric that offers a relaxed fit with plenty of stretch. Be sure to pick up the matching pants to complete your look! 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0203

    Category Name: Vacation Looks

    Price: $8.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropic Vibes Crop Top
    Get those tropical island vibes with this printed crop top! It features an off the shoulder square neckline, short sleeves, a tie front accent, a cropped hem, and a scalloped trim. The navy blue top is composed of a stretchy smocked fabric with an all over palm leaf print with hues of olive green and beige. Complete your vacay ready look with the matching maxi skirt!

    Style Number/Barcode: 06003-0247

    Category Name: Vacation Looks

    Price: $4.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Donna Chiffon Deep V Gown
    Special Occasion

    You never shy away from statement dressing—and our gorgeous Donna gown proves no exception! Rendered in a bold, black and marigold abstract print, Donna features adjustable spaghetti straps leading to a cross back, a deep V bodice with pleat detail at bust, a banded waist with back zip and hook-and-eye closure, and an A-line skirt. Dress is partially lined and made from a float-y, chiffon-like material with little to no stretch. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0164

    Category Name: Vacation Looks

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • To Paradise Printed Crop Top
    Whether you're jetting off to some place warm and exotic, or just chillin' wherever you're at, keep the spirit of the tropics near with this vibrant crop. Top features an all-over, multi-color leaf print, spaghetti straps, a sweetheart neckline, and seam detail at bust. Top slips on and is made from a soft, smooth material with a fair amount of stretch.

    Model is 5'6.5" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06001-1717

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Still A Rose Crop Top
    Bright and beautiful, this blossom-adorned bustier crop will let you shine. Top features an all-over rose print, adjustable spaghetti straps, gather-detailed underwire cups, and a lace-up tie back. Crop is made from a soft woven material with a touch of stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0244

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On The Lanai Floral Duster
    A featherweight layering piece that checks all of the style boxes? Yes, please! Count on this chic duster tying together all of your warm-weather looks. It features short flutter sleeves, a deep V neck leading to a three-button front closure, a smocked back waist, and a high-low hem. Duster is made from a chiffon-like material with little to no stretch.

    Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0239

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On The Lanai Floral Duster
    A featherweight layering piece that checks all of the style boxes? Yes, please! Count on this chic duster tying together all of your warm-weather looks. It features short flutter sleeves, a deep V neck leading to a three-button front closure, a smocked back waist, and a high-low hem. Duster is made from a chiffon-like material with little to no stretch.

    Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0238

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glam Attitude Three-Pack Hoop Earrings Set

    Give off a glam attitude with this elevated hoop earrings set! It features three pairs of small hoop earrings with a chic three-row sphere design, a sleek two-row classic design, and a trendy five-row textured design. Includes post-back closures. Style this set with a layered chain necklace.

    Fit & Features

    • Three-pack small hoop earrings set
    • Three-row sphere design
    • Two-row classic design
    • Five-row textured design
    • Post-back closures

     

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

    Style Number/Barcode: 07001-1975

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Time Floral Top
    A graphic pink and orange floral set against a rich navy background makes this crop especially eye catching. Top features crisscross adjustable spaghetti straps and an open tie back. Be sure and grab the matching maxi skirt to channel the perfect island vibe! Top is unlined and made from a lightweight woven material with little to no stretch.

    Style Number/Barcode: 06003-0276

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flow On Crop Top
    Go with the flow of this beautiful blouse! It features an elastic off the shoulder square neckline, long flowy sheer bell sleeves, and a cropped bubble elastic hem. The top is composed of a sheer chiffon fabric with a knit lining.

    Model is 5'8.5" with 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06003-0075

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flirty And Frilly Floral Top
    Get an absolutely adorable look with this flirty floral crop! The top features frilly ruffle short sleeves, a sweetheart neckline, a stretchy square back, vertical seams down the bust, and a cropped hem. The top is composed of a crepe fabric that offers moderate stretch.

    Model is 5'7" with 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06001-1698

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Easy Livin' Crochet Halter Top

    Take it easy this summer in this adorable crochet halter top! It features a sleeveless bodice, a halter neckline, bungee cord spaghetti straps that lead to a cross back, a low back with an exposed gold zipper closure, and a cropped hem with a scalloped hemline. The top is composed of a sheer crochet fabric with a short stretchy knit lining.

    Style Number/Barcode: 06003-0130

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked In Ruffles Mini Dress

    Keep it adorable and sweet in ruffles! This dress features a square neckline, sheer ruffled short sleeves and a mini length skirt with a ruffled hem. The all over print adds to this vibrant mini! Dress is composed of a stretchy smocked fabric that offers a form hugging fit. Includes a smooth knit lining.

    Style Number/Barcode: 05102-0298

    Category Name: Vacation Looks

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacation Mode Jumpsuit
    We are in vacation mode with this palm print jumpsuit! The jumper features a v neckline, spaghetti straps that cross in the back, as well as a colorful palm leaf pattern. The jumper is has a wide leg hem and is composed of a soft knit material and smooth inner lining at the cup area that offers moderate stretch. Time for a Pina Colada! 

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06502-0096

    Category Name: Vacation Looks

    Price: $4.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked Stunner Mini Dress

    Showcase the stylish stunner you are in this adorable smocked mini dress! It features a sleeveless bodice, thick smocked shoulder straps with ruffle detailing, a sweetheart neckline, a stretchy and smocked bust, a high waist seam with a ruffle trim, and a flowy skirt with a tiered ruffle hem. The dress is composed of a lightweight woven fabric with a woven skirt lining.

    Style Number/Barcode: 05102-0230

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay All Day Mini Dress

    Feel like you're on a vacay all day in this fun tropical printed mini! It features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, form hugging fit. The dress is composed of a scuba knit fabric that offers moderate stretch and showcases a vibrant print.

    Style Number/Barcode: 05102-0008

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smocked And Stylin' Mini Dress

    This adorable floral printed mini is smocked and stylin'! The dress features a sleeveless bodice, tie shoulder spaghetti straps, a square neckline with a bust keyhole cut out, a square back, pleated details, and a stretchy and smocked fit. The dress is composed of a lightweight linen fabric that offers a form hugging fit.

    Style Number/Barcode: 05102-0283

    Category Name: Vacation Looks

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Soft And Sweet Dress

    Show off your soft sweet side baby girl! This off shoulder dress is the perfect ensemble for a day in the sun. Featuring a straight off-shoulder neckline and wooden buttons down the middle, this dress has a form fitting bodice and a ribbed knit material that will offer maximum stretch as well as a soft inner lining. Show off those shoulders girl!

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-4039

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Get Sprung On Florals Mini Dress

    Get sprung on this too cute mini dress! It features an off the shoulder neckline with short cuffed sleeves, a trendy tie front with a keyhole cut out, seam detailing, a smocked back, and a short, form hugging fit. The dress is composed of a woven fabric with no stretch.

    Style Number/Barcode: 05102-0099

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Not So Basic Mini Dress

    Sure, you probably have your share of mini dresses. Now it's time for an of-the-moment upgrade! This ultra-chic mini features an off-the-shoulder elasticized neckline, gathered bodice and sleeves, a back zip, banded waist with back smocking, and pencil skirt with gather-drape detail. Dress is made from a mid-weight woven material with little to no stretch.

    Style Number/Barcode: 05101-0165

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral In Love Midi Dress
    Fall in love with this romantic floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline created by a knot front detail, a hidden back zipper and hook and eye closure, and an A-line mid-length fit with a front slit. The dress is composed of a lightweight woven fabric.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0209

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Elevated Chic Off-The-Shoulder A-Line Mini Dress

    Elevate any casual day in this off-the-shoulder mini dress! This stunning dress features a twisted bust accent for a trendy touch, an A-line silhouette, and a mini-length hem that creates a flattering fit on the smooth knit-lined fabric. Complete the look with luxe earrings for a dinner party!

    Fit & Features

    • Smooth knit lined fabric, moderate stretch
    • Off-the-shoulder neckline
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5755

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heaven Sent Button Front Mini Dress

    It's all about the details in this sweet, statement-making mini. Dress has a smocked bodice from bust to hem, an eye-catching button-down front, and eyelet trim at the shoulders, bust, and hem. Dress is made from a stretchy, medium-weight woven fabric.

    Style Number/Barcode: 05102-0226

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life's A Beach Mesh Dress

    Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.

    Style Number/Barcode: 05102-0159

    Category Name: Vacation Looks

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free