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.

  • Fierce Fashionista Clear Crossbody Purse

    Tap into your wild side with a crossbody that brings a fierce touch to your favorite outfits. The purse features an oversized clear rectangular body, a fold-over closure, and a leopard print trim. Complete look with a curve-hugging bodycon and clear heels. 

    Fit & Features 

    • Oversized rectangular body
    • Clear PVC body 
    • Fold-over closure with fasten closure
    • Leopard print trim 
    • Chain shoulder strap

    Style Number/Barcode: 07203-0357

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glow Getter Strapless Cutout Mini Dress

    Catch flights and compliments. This strapless mini hugs you in all the right places with a ruched bust ring detail and cheeky cutout that turns the charm up. Brunch, beach, or bae date—it’s a serve every time.

    Fit & Features

    • Rib knit stretchy fabric
    • Strapless sweetheart tube neckline with hardware trim
    • Cutout accent
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000033

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Poised Polka Dot Tie Front Top

    Keep it poised in a polka dot top to keep your looks on-trend this season. The top features a polka dot pattern, long sleeves and tie front bodice with a sexy cropped hem. Complete your look with high waist shorts and sunglasses for a day-date ready look.

    Fit & Features

    • Polka dot pattern
    • Tie-front bodice
    • Long sleeves
    • Cropped hem
    • Lightweight woven fabric
    • Relaxed fit 

     

    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0567

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Step Out Faux Leather Flat Sandals

    Step out in sleek sandals for an effortlessly casual vibe. The sandals feature a quick slip-on design, a wide faux leather strap, and narrow asymmetrical straps that cross over the toe. Complete outfit with a floral maxi dress and sunglasses for a vacation-ready outfit. 

    Fit & Features

    • Slip-on design
    • Wide faux leather strap
    • Asymmetrical straps that cross over the toe 

    Style Number/Barcode: 07404-0527

    Category Name: Vacation Looks

    Price: $12.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tie-Dye Satin Cowl Neck Mini Dress

    Keep it chic in a tie-dye dress to brighten your cute summer fits girl! The dress features a sleeveless bodice, a cowl neckline, sleek spaghetti straps, and a pretty pastel tie-dye print. Complete your look with a chic scrunchie and a dainty charm necklace.

    Fit & Features

    • Sleeveless bodice
    • Cowl neckline
    • Tie-dye print
    • Mini length silhouette
    • Satin fabric
    • Relaxed fit 

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0812

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet Stripes High Waist Shorts

    Keep it sweet and chic in striped shorts that keep your fall fits' on point. The shorts feature an elastic high rise waist, hidden side pockets to keep essentials close to you, and narrow vertical stripes that streamline. Complete outfit with the matching top, matching face mask to stay safe, and chunky dad sneakers for an effortlessly casual vibe. 

    Shop Matching Top: Sweet Stripes Dolman Sleeve Crop Top

    Shop Matching Face Mask: Reusable Striped Face Mask with Earloops

    Fit & Features

    • High rise waist
    • Hidden side pockets
    • Wide leg hem
    • Vertical narrow stripes
    • Matching top sold separately  
    • Matching face mask sold separately

    Style Number/Barcode: 06503-0169

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off The Shoulder Floral Smocked Top

    Impress in a floral top this season for an effortlessly cute look. The top features an off the shoulder neckline, a smocked bodice, long chiffon sleeves and a gorgeous floral print throughout. Complete your look with high waist shorts and sunglasses. 

    Fit & Features 

    • Off the shoulder neckline
    • Long sheer chiffon sleeves
    • Smocked bodice
    • Floral print
    • Relaxed fit  


    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small. 

    Style Number/Barcode: 06003-0915

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Eyelet V Neck Skater Romper

    Keep it chic in an eyelet romper. This summer-ready eyelet romper features a sleeveless bodice, a plunging wrap V-neckline and spaghetti straps that lead to a partially open back. The relaxed fit bodice leads to a pair of wide-leg shorts complemented with a skater overlay silhouette. The romper is composed of a lightweight woven fabric that offers a relaxed fit with a slight stretch. Complete look with sunglasses and wedges for a vacation-approved look. 

    Fit & Features

    • Plunging v-neckline
    • Spaghetti straps 
    • Eyelet design 
    • Wide-leg shorts
    • Lightweight woven fabric
    • Relaxed fit 
    • Slight stretch 

    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06503-0120

    Category Name: Vacation Looks

    Price: $21.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oversized Floppy Straw Hat

    Channel vacay vibes in a floppy hat that brings the drama. The oversized hat features a traditional floppy design and a straw material composition. Complete outfit with a floral sundress and strappy sandals. 

    Fit & Features

    • Oversized design
    • Floppy brim
    • Straw material composition

    Style Number/Barcode: 07302-0167

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Rise Acid Wash Cargo Shorts

    Keep it laidback in cargo shorts to rock those casual vibes. The shorts feature a high rise waist, a single button with zipper closure and small cargo pockets. Complete your casual outfit with a basic bodysuit and trendy dad sneakers. 

    Fit & Features

    • High rise waist
    • Single-button with zipper closure  
    • Side pockets
    • Small cargo pockets
    • Acid wash denim fabric


    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size three.

    Style Number/Barcode: 06603-0133

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On the Rise Destructed Fringe Shorts

    Get those good vibes going in shorts that keep your fits' looking effortlessly put together. The shorts feature a high rise waist, a light-medium wash, and light destruction with fringed hem. Complete look with a basic bodysuit and trendy dad sneakers to keep look on point. 

    Fit & Features

    • High rise waist
    • Single-button with zipper closure
    • Traditional five-pocket design 
    • Light-medium wash 
    • Light destruction
    • Fringed hem 

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size three.

    Style Number/Barcode: 06603-0136

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Too Sweet Sweetheart Ditsy Floral Mini Dress

    You'll look too sweet in a floral dress that brings the charm. This pretty date-night dress features a sweetheart neckline, a tie front accent, and a ditsy floral print. Complete your look with a light wash denim jacket and wedges. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Tie front accent at the center of the bodice
    • Spaghetti straps 
    • Ditsy floral print
    • Mini length silhouette

     

    Model is 5'8" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0767

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Step Up Crop Lace-Up Top

    Step up your crop top game in this cute lace-up for a fab day out. The crop top features a square neckline, a cropped hem, and a bold open back with lace-up ties to create a sexy design. Complete look with your favorite high waist jeans and a chic Panama hat. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cropped hem
    • Open back with lace-up straps
    • Brushed knit fabric

     

    Style Number/Barcode: 06001-2864

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Cute Pajama Satin Cami and Shorts

    These adorable satin pajamas will have you feelin' really cute! This must-have pajama set features a cropped cami with lace trim and adjustable spaghetti straps. The matching shorts feature a mid-rise fit, wide-leg hem and lace trim. Complete your look with sleek slides. 

    Fit & Features

    • Two-piece set 
    • V-neckline 
    • Cropped cami
    • Adjustable spaghetti straps
    • Lace trim
    • Satin fabric

     

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

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

    Style Number/Barcode: 07103-0343

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • What's The Scoop Ribbed Tank Bodysuit

    Bring a scoop of style in a fab bodysuit to style with all your effortlessly casual outfits. The bodysuit features a scoop neckline with a matching scoop back, tank-like straps, and is composed of a ribbed compression knit fabric. Style the basic tank bodysuit with high waist denim and statement sunglasses.

    Fit & Features

    • Scoop neckline
    • Tank-like straps
    • Ribbed compression knit fabric
    • Plenty of stretch
    • Form-hugging fit

    Style Number/Barcode: 06002-0595

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Date Lace-Up Espadrille Wedges

    These lace-up espadrille wedges will make a cute finishing touch for your date this weekend! 

    Fit & Features

    • Wedge heel
    • Almond toe with crisscross straps
    • Lace-up ankle straps
    • Espadrille material
    • Runs true to size

    Style Number/Barcode: 07406-000001

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Escape Sleeveless Striped Romper

    Escape to the topics in a romper that brings those vacay vibes girl! The romper features a sleeveless square-neck bodice, paper bag shorts with a tie waist belt, and a tropical palm-leaf print with stripes. Complete outfit with wedges and sunglasses for your vacay-approved look. 

    Fit & Features

    • Sleeveless bodice
    • Square neckline
    • Paper bag shorts
    • Tie-waist belt
    • Tropical palm leaf print
    • Stripes 
    • Hidden side pockets

     

    Model is 5'8" with a 32" bust,  24 waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06303-0093

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Moment Chiffon Kimono

    Create a floral moment in a chic kimono to layer with all your favorite basic pieces. This kimono features a floral print, a drape open front, and comfortable kimono sleeves. Complete outfit with high waist denim and wedges. 

    Fit & Features

    • Floral print
    • Draped open front 
    • Kimono short sleeves
    • Lightweight chiffon fabric
    • Relaxed fit 

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0545

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adore You Floral High Slit Maxi Dress

    Feel adored in a floral dress that brings some serious butterflies this season. The dress features a gorgeous floral print, a flattering cowl neckline, and a maxi length silhouette that is accented a high side slit. Complete your date-night ready outfit with sleek hoop earrings and strappy heels that mesmerize. 

    Fit & Features

    • Sleeveless bodice
    • Cowl neckline
    • Spaghetti straps that cross at the back
    • Floral print
    • Maxi length silhouette
    • High side slit
    • Smooth knit fabric, form-hugging fit

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0529

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready To Move Square Neck Ruched Mini Dress

    Make a move in this ruched mini dress that brings the heat for your next night out with the girls. The dress features a square neckline and a curve-hugging mini length silhouette with a ruched drawstring hem. Complete look with statement hoops and glam heels. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini length silhouette
    • Ruched drawstring hem
    • Smooth knit fabric 
    • Form hugging fit

     

    Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05103-1174

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Scooped In Style Sleeveless Cutout Ribbed Maxi Dress

    Serve up a stylish look in a maxi dress that slays girl! Step out in this dress that features a sleeveless bodice, a scoop neckline with tank-like straps, a sexy mid-drift cutout to show off a hint of skin, and a maxi length silhouette with twist front accent to reveal a mini length skirt. Complete outfit with wedges and fringe earrings. 

    Fit & Features 

    • Sleeveless scoop neckline
    • Tank-like straps
    • Mid-drift cutout
    • Maxi length silhouette overlay with twist front accent 
    • Mini length skirt 
    • Ribbed knit fabric 
    • Form hugging fit

     

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0462

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweet like Candy Ruffle Mini Dress

    You’ll be looking sweet for date night in this fab mini dress! It features spaghetti straps, a wrap-front V neckline, front ruching, and a short, form-hugging fit with an asymmetric ruffled front hem. Style the dress with clear heels and a trendy mini bag.

    Fit & Features

    • Spaghetti straps
    • Wrap-front V neckline
    • Ruched detailing
    • Mini-length, asymmetric ruffled hem
    • Curve-hugging silhouette
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4088

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spaghetti Strap Wide Leg Jumpsuit

    Keep it chic in fab jumpsuit for your next brunch date! The jumpsuit features spaghetti tie straps to create a custom fit, a square neckline with shirring at the bust and a flared culotte leg. Style jumpsuit with clear heels and statement earrings.

    Fit & Features

    • Sleeveless bodice
    • Spaghetti tie straps
    • Square neckline with shirring at the bust
    • Empire waist
    • Flared culotte leg

     

    Model is 5'8" with 32" bust, 26" waist and 38" hips. She is wearing a size small.

    Style Number/Barcode: 06402-0258

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daisy Days Smocked Mini Dress

    Keep it fab in florals this season with this charming mini dress! Pair with wedges and a cute tote for the perf lewk honey! 

    Fit & Features 

    • Square Neckline | Smocked Trim
    • Inset | Tie at Bust 
    • Spaghetti Tie Straps 
    • Daisy Floral Print
    • Smocked Knit Fabric 
    • Form Hugging Fit 
    • Moderate Stretch 

     

    Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

     

    Style Number/Barcode: 05102-0684

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance