Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Sight To See V-Neck Slip Dress

    You'll be a sight to see in this casual slip dress perfect for dinner and drinks with your bae! It features a sleeveless v-neck, bungee spaghetti straps, a curve-hugging silhouette, and a short-length hem.  Style with earrings and heels to complete the look!

    Fit & Features

    • Sleeveless v-neck
    • Bust lining
    • Bungee spaghetti straps
    • Curve-hugging silhouette
    • Short-length hem
    • Texture knit design, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4840

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Vacay Halter Lace-Up Maxi Dress

    Your next vacay fit is here - say aloha to this knit maxi dress designed to showcase your curves in a bodycon fit and bare some skin with the alluring lace-up back.

    Fit & Features

    • Texture knit fabric, knit lining, moderate stretch
    • High halter neckline
    • Spaghetti straps
    • Lace-up back
    • Bodycon fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000053

    Category Name: Vacation Looks

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hit The Basics Mock Neck Crop Top

    A basic crop top like this is essential for creating the perfect capsule closet! It features fitted long sleeves, and a mock neck, and is composed of stretchy knit fabric. Style with jeans, a coat, and new shoes to complete the look! 

    Fit & Features

    • Fitted long sleeves
    • Mock neck
    • Cropped hem
    • Stretchy knit fabric, double-lined
    • Runs true to size

    Style Number/Barcode: 06002-1491

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lasting Romance Strapless Lace Crop Top

    Romance yourself in this strapless lace crop top perfect for teaming with cute shorts!

    Fit & Features

    • Semi-lace lined fabric
    • Strapless sweetheart neckline
    • Twisted lined bust
    • Center split accent
    • Sheer bodice
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5722

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: BANANA, IVORY

    Available Size: XS, S, M, L

  • Chill Cutie Cable Knit Sweater

    Cutie alert! Keep chill and cozy in this cable knit sweater featuring long sleeves with ribbed cuffs, a surplice v-neckline, and a cropped hem of soft knit fabric. Complete the look in a basic cami and jeans.

    Fit & Features

    • Long sleeves with ribbed cuffs
    • Surplice v-neckline
    • Cropped hem
    • Cable knit design
    • Soft and comfortable
    • Fits true to size

    Style Number/Barcode: 06005-1484

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sun-Kissed Aesthetic Starfish High Slit Maxi Skirt

    Achieve a sun-kissed aesthetic in this sultry maxi skirt boasting a high front slit with a beachy starfish accent. This skirt is perfect for vacations or pool parties! 

    Fit & Features

    • Smooth stretchy knit fabric, panty lining
    • Mid-rise waist
    • Starfish accent
    • High front slit
    • Flowy maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06501-000029

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: M, L

  • Casual Staple Wrap-Front Mini Dress

    Update your wardrobe with this cute and casual mini dress that is a stylish staple! It features a crew neckline, short sleeves, a trendy wrap-front design at the waist with a tie closure, a form-hugging fit, and a mini-length hem. The soft brushed knit fabric offers plenty of stretch for comfort. Complete the look with ankle booties.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Wrap-front design at the waist, tie closure
    • Form-fitting silhouette
    • Mini-length hem
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5007

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Undeniable Charm Gingham Ribbon Halter Crop Top

    Make your way looking charming in this halter crop top with a trendy gingham ribbon trim, it's essential for picnics, day dates, and outdoor BBQs! 

    Fit & Features

    • Woven fabric, bust knit lining
    • Halter V-neckline with gingham ribbon trim
    • Stretchy smocked back
    • Fitted crop hem
    • Runs true to size

    Style Number/Barcode: 06003-000013

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: L

    Product Badge:
    • Sale
  • Feline Fierce High-Slit Midi Skirt

    You'll be feelin' fab and fierce in this adorable leopard printed midi skirt. It features a high-rise waist, a chic high front slit, and a mid-length, relaxed silhouette. Style this skirt with a basic bodysuit and cute mules.

    Fit & Features

    • High-rise waist, elastic-band
    • High front slit
    • Mid-length, relaxed silhouette
    • Lightweight knit fabric, moderate stretch
    • Leopard print
    • Runs true to size

    Style Number/Barcode: 06501-0513

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fruity Delight Three-Pack Earrings Set

    Freshen up your accessories with this three-pack earrings set for a delicious spring season! the set features one pair of rhinestone cherries, one pair of strawberries, and one sleek ball studs. Pair with a shoulder bag.

    Fit & Features

    • Three-pack set
    • One rhinestone cherry pair, post-back closure
    • One strawberry pair, clasp closure
    • One ball stud pair, post-back closure

     

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

    Style Number/Barcode: 07001-2300

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Dream Floral Strappy Maxi Dress

    POV: You just entered the group chat looking like a vacay dream. This mesh maxi dress hugs in all the right places with a strappy back that turns heads on vacation and summer parties!

    Fit & Features

    • Tropical floral print, mesh-lined fabric, moderate stretch
    • V-neckline
    • Bungee spaghetti straps
    • Strappy open back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000389

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L, XL

  • Adorable Factor Chiffon Sweetheart Midi Dress

    Raise the bar looking adorable in this chiffon midi dress perfect for upcoming dressy occasions! The midi-length dress features short puff sleeves, a sweetheart neckline, a ruched bust, and a flirty cutout waist to show some skin. The flattering A-line silhouette boasts a playful front slit and a flowy midi hem. Complete the look with cute sandals and jewelry!

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline, stretchy smocked back
    • Ruched bust, cutout waist
    • A-line silhouette, front slit
    • Midi-length hem
    • Chiffon woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-3189

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Truly Charming Sleeveless A-Line Mini Dress

    Unlock a truly charming style in this sleeveless mini dress at BBQs to summer picnics! Features a square neckline and adjustable spaghetti straps for the perfect fit. Its A-line silhouette flatters every figure, and the mini-length hem adds flirtatiousness. Complete the look with sunglasses and wedges.

    Fit & Features

    • Woven fabric, minimal stretch
    • Square neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5704

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lowkey Head Turner Open Back Mini Dress

    She’s simple until she turns around. This bodycon mini dress elevates your look with an open back and tie detail that’s anything but basic. Pair with sandals for daytime outings.

    Fit & Features

    • Rib knit fabric, smooth, stretchy knit lining
    • Crew neck
    • Open back with tie detail
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000159

    Category Name: Vacation Looks

    Price: $29.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Sunny State Mid-Rise Distressed Denim Shorts

    Grab your besties and make plans to rock these mid-rise denim shorts for fun under the sun! The mid-rise waist and form-hugging fit flatter your curves, while the distressed accents and cut-off hem add a touch of edge. Complete the look in a cute bodysuit and platform sneakers!

    Fit & Features

    • Denim fabric, minimal stretch
    • Mid-rise waist
    • Distressed accents, cut-off hem
    • Form-hugging
    • Front button and hidden zipper closure, five-pockets
    • Runs true to size

    Style Number/Barcode: 06603-0388

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: S, L, XL

  • Tropical Vacay Spaghetti Strap Tie-Back Crop Top

    The perfect tropical floral crop top to look stylish on your vacay! With its sleeveless V-cut neckline with ruching at the bust, spaghetti straps, and a tie-back design, this top offers a trendy silhouette. The fitted ultra-cropped hem and eye-catching tropical floral print add a touch of boldness to your look. Pair with the matching midi skirt and espadrille wedges! 

    Shop Matching Bottoms: Tropical Vacay High-Rise Slit Midi Skirt

    Fit & Features

    • Tropical floral print
    • Stretchy knit fabric
    • V-wired neckline, ruched bust
    • Spaghetti straps
    • Tie-back design
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06001-5221

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Places To Be Off-The-Shoulder Top

    You've got places to be so don't compromise your style! This off-the-shoulder top creates an effortlessly cute look with your favorite bottoms. It features dolman long sleeves with fitted cuffs, a slouchy bodice, and a fitted hem on stretchy textured knit fabric. Complete the look in best-selling jeans.

    Fit & Features

    • Off-the-shoulder
    • Dolman long sleeves, fitted cuffs
    • Slouchy bodice
    • Fitted hem
    • Textured knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4638

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Girly Fave Ruffled Eyelet Knit Romper

    This eyelet knit romper will be your new girly fave for the summer months! Designed with a strapless neckline, drop waist, and tiered ruffled overlay, style with sneakers.

    Fit & Features

    • Eyelet knit fabric
    • Strapless straight neckline
    • Drop waist design
    • Tiered ruffled mini-length overlay
    • Hidden fitted shorts
    • Runs true to size

    Style Number/Barcode: 06503-000022

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: L

    Product Badge:
    • Sale
  • Snap To It Tweed Tank Mini Dress

    Snap into this nineties-inspired tweed mini dress to have your major fashion moment! It features a sleeveless square neck, wide shoulder straps, and a bodycon fit. The dress is composed of a multi-colored stitch tweed woven fabric with a smooth satin lining with no stretch. Style with a cropped blazer to complete the look!

    Fit & Features

    • Sleeveless square neck
    • Wide shoulder straps
    • Back zipper and hook-eye closure
    • Bodycon fit, mini-length hem
    • Multi-colored stitch tweed fabric
    • Smooth satin lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2245

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darling Flirtation Tie Strap V-Neck Floral Mini Dress

    Imagine how darling and flirty you'll be in this floral mini dress at brunch and parties! The delicate floral print on brushed knit soft fabric adds a playful and romantic touch, perfect for any occasion. Features a plunging neckline and charming tie straps to accentuate your curves while the bodycon fit and mini-length hem add a touch of allure. Complete the look in cute sandals.

    Fit & Features

    • Floral print, brushed knit fabric lined with stretchy knit
    • Tie straps, V-neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5589

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Down Oval Sunglasses

    The perfect pair of oval sunglasses to throw on and go on your next adventure or coffee run!

    Fit & Features

    • Colored frames
    • Tinted oval lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1133

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: WINE

    Available Size: NS

  • Spine Chilling Eyelash Knit Sweater

    This eyelash knit sweater may give you chills at how cute it is! The sweater features long sleeves with cuffs, a mock neckline, cropped hem, and a partial open-back design with tie closure. Complete the look in a mini skirt and boots.

    Fit & Features

    • Long sleeves with cuffs
    • Mock neckline
    • Cropped hem
    • Partial open-back design tie closure
    • Fuzzy eyelash knit
    • Fits true to size

    Style Number/Barcode: 06005-1480

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sweeten Up Strappy Back Floral Chiffon Skater Dress

    Sweeten up any moment in this floral chiffon skater dress perfect for celebrations and showers! With a square neckline, spaghetti straps, and a playful strappy back design, this dress is perfect for any occasion. The skater silhouette and ruffled short-length hem add a flirty touch, while the ditsy floral print and chiffon fabric keep it light and whimsical. Complete the look in wedges.

    Fit & Features

    • Ditsy floral print, chiffon fabric lined with stretchy knit
    • Spagehtti straps, square neckline
    • Strappy back design
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5450

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back To Shore Crochet Cover Up Dress

    You'll love this crochet cover up dress to pack with you on every vacation or beach day! With a plunge neckline with a chic hoop insert and form-hugging fit, this dress is perfect for layering over a swimsuit.

    Fit & Features

    • Sheer crochet knit fabric
    • Long sleeves, flare cuffs
    • Plunge neckline, hoop insert
    • Form-hugging fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000054

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: M, L