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.

  • Floral Chic Mini Dress

    Add some floral chic to your pretty look with this adorable mini dress! It features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with a tie front detail, a square back with a hidden zipper and hook and eye closure, a high waist seam, and a flowy A-line skirt. The dress is composed of a woven fabric with a skirt lining, and offers no stretch.

    Style Number/Barcode: 05102-0224

    Category Name: Vacation Looks

    Price: $15.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flow With It Maxi Dress

    Go with the flow of this pretty summer maxi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a stretchy smocked square back, a front crochet top with sheer insets at the waist, and a long, floor length flowy maxi skirt with a front high thigh slit. The dress is composed of a linen fabric with no stretch.

    Style Number/Barcode: 05102-0085

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • All Eyelets On Me Dress

    All-over eyelet detail lends this mini its sweet summertime chic. Dress features ruffle-trim straps, a scoop neck with cutout keyhole detail, a gathered empire-style bodice, and a gently pleated A-line skirt with ruffle hem. Dress is fully lined, slips on, and is made from pure cotton with little to no stretch.

    Style Number/Barcode: 05102-0076

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffled And Rowdy Dress

    Dance around and get rowdy in ruffles! This adorable mini dress features a v-neckline with a snap and hook closure. The bodice of this dress is line with a ruffled trim, thick ruffled straps that lead to a low back, with a hidden zipper and a self tie bow. The skirt is adorned with a tiered ruffle effect. The dress is composed of a chiffon style material and offers no stretch yet, a flowy fit and includes a smooth inner lining. Now take a twirl! 

    Style Number/Barcode: 05102-0206

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Astrid Chiffon Floral Gown
    Special Occasion

    A bold black background makes the florals on our chiffon Astrid gown positively pop! She features a surplice-style V back and bodice with adjustable spaghetti straps, a self-tie belt, and a gently pleated full skirt with back zip. Astrid is lined to approximately mid thigh and semi-sheer from mid thigh to hem. She is made from a lightweight, chiffon-like material with little to no stretch.

    Model is 5’9” with a 32” bust, 24.5 waist, and 35” hips. She is wearing a size small.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0099

    Category Name: Vacation Looks

    Price: $29.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Loving Knit In Florals Maxi Dress

    Create a look to fall for in charming florals! The dress features a V neckline, shoulder tie straps, an elastic waist and a sweeping floor length maxi length. Dress is composed of a stretchy smooth knit fabric that offers a form hugging fit.

    Style Number/Barcode: 05101-0016

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Color Wheel Striped Mini Dress

    Rendered in bright stripes, this mini makes an impact. Dress features a fitted bodice with off-the-shoulder neckline, contrast gently pleated, A-line skirt, and a gathered elasticized waist with decorative tie. Dress is made from a soft, lightweight woven material with stretch through the bodice and waist.

    Style Number/Barcode: 05102-0000

    Category Name: Vacation Looks

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Connection Mini Dress

    Make a sweet connection in florals! This must have mini dress features a sleeveless bodice, a cowl neck, spaghetti straps and a mini length silhouette to show glowing gams! The neutral tone is complemented with pretty florals throughout! Dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch.

    Style Number/Barcode: 05102-0086

    Category Name: Vacation Looks

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Don't Be Ditsy Floral Dress
    Keep it short and sweet in this beige ditsy floral-print mini in pink, purple, and green. Dress features an elastic square neckline, gathered short peasant sleeves, side smocking detail, all-over gathering, and a ruffle-trim hem. Dress is partially lined with a cotton-like knit fabric and made from a gather-effect woven material with moderate stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0180

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • New Leaf Linen Mini Dress

    A lovely leaf print lends this green and white linen mini its easy sweetness. Dress features adjustable tie straps, a seamed bodice with ruffle trim and back zip, and a slight A-line skirt with ruffle hem. Dress is lined and made from a lightweight cotton blend with little to no stretch.

    Style Number/Barcode: 05102-0266

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffle Things Up Satin Mini Dress
    Make their hearts beat a little faster in this sexy light blue mini dress! It features a sweetheart neckline with a ruffle trim, narrow sleeves with a complementing ruffle trim, bustier style cups with underwire, a hidden back zipper closure, and a body-hugging silhouette. Dress is composed of a lined, satin knit fabric with minimal stretch. 

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

    Style Number/Barcode: 05103-0071

    Category Name: Vacation Looks

    Price: $10.00 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy And Cool Twill Layered Hoodie Jacket

    Stay cozy and cool this season with this trendy crop jacket as a stylish layer perfect for chill nights! With long sleeves, snap-button cuffs, and a collar neckline, this jacket provides both warmth and style. The front snap-button-up closures and flap pockets add functionality, while the fleece-lined zip-up hoodie gives an extra layer of warmth. Complete the look with cute platform sneakers.

    Fit & Features

    • Twill woven fabric
    • Collar neckline
    • Front snap-button up closures, flap pockets
    • Cropped length
    • Fleece-lined zip up hoodie layer
    • Runs true to size

    Style Number/Barcode: 06204-1832

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Purrfect Mesh Cover Up
    This mesh cover up is the purrfect addition to your swim look! It features a wide crew neckline, long sleeves, and a form hugging fit with a mini dress length. The leopard print cover up is composed of a sheer mesh fabric with plenty of stretch.

    Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

    Style Number/Barcode: 06001-1219

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Crochet Lace Skater Dress
    This crochet lace skater dress will be your go-to spring 'fit! It features a sleeveless bodice, spaghetti straps, a V neckline, a back zipper closure, a high waist seam, and a short, flowy skater skirt. The blue dress is composed of a sheer crochet lace fabric with a full knit lining. 

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-8649

    Category Name: Vacation Looks

    Price: $10.00 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Movin' And Groovin' Tube Top

    This fun and trendy tie dye tube top will have you movin' and groovin'! It features a sleeveless strapless padded sweetheart neckline with a tie front closure and a majorly cropped hem. The top is composed of a ribbed knit fabric that offers moderate stretch. Don't forget the matching shorts to complete your look!

    Style Number/Barcode: 06001-1684

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ladies Who Brunch Wrap Midi Dress

    Hit your fave weekend spots in high style in this wrap-effect midi dress. Dress has a V neck, adjustable spaghetti straps, hook-and-eye zip closure, and wrap tie at side. Dress is lined in cotton and made from a linen-like woven fabric with little to no stretch.

    Style Number/Barcode: 05102-0237

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dark and Floral Dress

    Sweep them away as your dress sweeps the floor you walk on queen. This maxi gown is comprised of a v neckline and v back line, spaghetti straps, lining in the upper chest area, and an attached self-tie bow in the back so that you may cinch it to your comfort.This floor length dress is composed a soft knit fabric with moderate stretch.

    Style Number/Barcode: 05101-0015

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bring A Bouquet Floral Romper
    A delicate floral print and standout details make this of-the-moment ivory romper a must right now. Romper features a strapless bodice, elasticized decorative tie waist, and ruffle-trim flowy shorts. Romper is fully lined and made from a silky woven material with stretch at the waist and bust.

    Style Number/Barcode: 06403-0031

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wide Fit Stylishly Stacked Heels
    Stylishly level up your look with these chic stacked heels! They feature an open toe with a thick faux leather black strap, a wide fit, an around the ankle adjustable black strap, stud detailing along the sides, an open heel, and a stacked block heel. The shoes are composed of a faux leather material.

    Style Number/Barcode: 07401-0155

    Category Name: Vacation Looks

    Price: $12.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunshine Glow Mini Dress
    Get that sunny glow in this must have mini dress for the summer! It features a sleeveless bodice, adjustable spaghetti straps that cross in the back, a V neckline with a front hook and eye closure, a hidden back zipper and hook and eye closure, tiered ruffled detailing, and an overall flowy fit. The dress is composed of a linen fabric with a full lining and features an all over pretty floral print.

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0147

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wrapped In Beauty Mini Dress

    Wrap yourself in this gorgeous mini dress to showcase your beauty! The dress features a sleeveless bodice, a wrap V neckline, a tie waist belt and an asymmetrical mini skirt. Dress is composed of an unlined crepe fabric that offers a form hugging fit with a moderate stretch.

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

    Style Number/Barcode: 05102-0239

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rowan Floral Chiffon Formal Dress
    Special Occasion

    Floaty and feminine, our diaphanous burgundy Rowan dress is perfect for warm-weather special occasions. She features adjustable spaghetti straps, a V neck and back, crisscross ties at waist, zipper closure, and a gently pleated, semi-lined modified A-line skirt. Chiffon-like fabric is semi sheer from mid-thigh to hem and offers little to no stretch. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0006

    Category Name: Vacation Looks

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strappy Comfort Wedge Heels

    Keep it chic and comfortable in these must have wedges! They feature an open back, an adjustable ankle strap, a multi strap design with open toe and a wedge heel. 

    Style Number/Barcode: 07406-0033

    Category Name: Vacation Looks

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ready To Ruffle Mini Dress
    You'll be ready to ruffle in this flirty little mini dress! It features a sleeveless bodice, a V neckline with an adorable tie closure followed by a front cut out, button detailing starting at the waist, a hidden back zipper and hook and eye closure, and a cute tiered ruffle hem. The dress is composed of a linen fabric with no stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0149

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance