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.

  • Classic Chic Mock Neck Sweater Dress

    This classic chic sweater dress is perfect for styling up or down this winter season. It features an on-trend mock neckline, long fitted sleeves, a short, curve-hugging silhouette, and a front slit accent. The knit fabric offers plenty of stretch. Pair with knee-high boots and sleek hoops.

    Fit & Features

    • Ribbed mock neckline
    • Long fitted sleeves
    • Mini-length hem, front slit
    • Curve-hugging silhouette
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1616

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Resort-Ready Tropical Print Mesh Duster

    You'll be resort-ready when you pack this tropical print mesh duster in your carry-on! It features long fitted sleeves, an open front, a long-length hem with a flowy silhouette, and a multi-colored tropical print pattern on the airy sheer mesh fabric. Style over a mini dress with clear heels!

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Long-length hem
    • Flowy silhouette
    • Multi-colored tropical print
    • Sheer mesh fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06202-0436

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Effortless Square Neck Rib Knit Bodysuit

    All you need is this sleeveless basic bodysuit and your fave denim to create a simply effortless and cute look! Crafted from stretchy rib knit fabric that fits like a glove, this bodysuit boasts a square neckline, tank shoulder straps, and a thong bottom with snap-button closures for convenience. Style with high-rise denim jeans and sandals.

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Tank shoulder straps
    • Thong bottom, snap-button closures
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 07109-0367

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back Of My Mind Crepe Slip Dress

    You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Form-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4826

    Category Name: Vacation Looks

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fave Trend Oversized Cat-Eye Sunglasses

    These fab oversized cat-eye sunglasses will be your new fave trend to style up! They feature a cat-eye rimless design, a thin metal nose bridge, thin metal arms with a front cutout, rubber nose pads for support, and gradient-tinted lenses with stud accents. Pair with hoop earrings and a mini handbag for an everyday 'fit.

    Fit & Features

    • Oversized cat-eye rimless design
    • Thin metal nose bridge and arms, cutout details
    • Rubber nose pads
    • Gradient-tinted lenses, stud details
    • 100% UV protection

    Style Number/Barcode: 07008-1073

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Harmony Chiffon Midi Dress

    Your sweet style personality goes in harmony with this chiffon midi dress perfect for any upcoming weddings and parties! The knee-length dress features short puff sleeves, a sweetheart neckline, princess seams, and a front flirty slit along the A-line silhouette. Pair with a chic ring set and heels.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck
    • Princess seams, front slit, back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Airy chiffon fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1850

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance For Two Sleeveless Crop Top

    You'll be sure to fall in love with this crop top for a dreamy summer wardrobe! With its square neckline, adjustable spaghetti straps, and crop hem, you'll feel effortlessly elegant. Complete the look with the matching bottoms.

    Shop Matching Bottoms: Romance For Two High Rise Slit Maxi Skirt

    Fit & Features

    • Gauze woven fabric, partially woven lining
    • Adjustable spaghetti straps
    • Square neckline
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2420

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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: $6.97 $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
  • Fierce And Trendy Mid-Rise Leopard Mini Skort

    Unleash your fierce and trendy side in this leopard mini skort! The belted waist and pleated skirt overlay create a trendy look while the mini hem shows off your legs.

    Fit & Features

    • Leopard print, denim fabric
    • Mid-rise belted waist, belt loop accents
    • Pleated skirt overlay, side zipper closure
    • Shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06603-0430

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • 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
  • 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
  • Pretty Pleats High-Rise Chiffon Palazzo Pants

    Pretty pleats make these high-rise palazzo pants a chic find! Style with a crop top and heels for dinner and drinks.

    Fit & Features

    • Chiffon woven fabric, knit lining
    • High-rise waist
    • Wide-leg pleated silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1465

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: Out of Stock

    Product Badge:
    • Ships Free
  • 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