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.

  • Wild Style Zebra Print Mini Skirt

    Show off a wild style in this trendy zebra print mini skirt! It features a high-rise waist, a ruched front seam leading to a chic slit, a mini-length hem, and a form-hugging fit. Complete the look with the matching crop top and a pair of clear heels.

    Shop Matching Top: Wild Style Zebra Print Crop Top

    Fit & Features

    • High-rise waist
    • Ruched front seam
    • Front slit
    • Mini-length hem, form-hugging fit
    • Zebra print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06501-0786

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: M

    Product Badge:
    • Sale
  • Wanderlust Paisley Print Knit Flare Pants

    You'll be a wanderlust beauty in these paisley print flare pants, perf for creating a dreamy desert festival look! The soft and stretchy brushed knit fabric features a bohemian-inspired paisley print pattern for those effortlessly cool vibes. The high waist has an elastic band for comfortable wear. The hip-hugging fit continues through the leg, leading to a trendy flared hem. Style with a crop top and ankle booties.

    Fit & Features

    • Stretchy brushed knit fabric
    • Paisley multi-print pattern
    • High-rise elasticized waist
    • Hip-hugging fit
    • Flared hem
    • Runs true to size

    Style Number/Barcode: 06502-2439

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Cozy Henley Button Skinny Leg Jumpsuit

    This henley button skinny-leg jumpsuit is perfect for a cozy day out. Made from stretchy seamless rib knit fabric, it offers both comfort and style. The scoop neckline features snap-button closures for added detail while the form-hugging fit and skinny-leg design create a flattering silhouette. Complete the look in platform sneakers and a crop jacket!

    Fit & Features

    • Seamless stretchy rib knit fabric
    • Snap-button closures
    • Form-hugging fit
    • Skinny-leg design
    • Runs true to size

    Style Number/Barcode: 07109-0387

    Category Name: Vacation Looks

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Cutie Halter Ruffle Mini Dress

    Make this halter mini dress a staple this season! The form-hugging silhouette accentuates your curves in all the right places, while the playful ruffled hem adds flirty movement. Style with strappy heels.

    Fit & Features

    • Texture knit fabric, moderate stretch
    • Cowl neckline
    • Spaghetti straps with hoop inserts
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000132

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Effect Utility Woven Crop Jacket

    A versatile woven jacket that brings a cool effect to every outfit! Layer on this twill jacket with slouchy long sleeves and elasticized cuffs to keep you warm, a collar neckline with button closure, and a front button-up design. With flap pockets and an adjustable drawstring crop hem, you'll have both function and fashion. Complete the look with trendy boots for casual plans!

    Fit & Features

    • Twill cotton woven fabric
    • Flap pockets
    • Button-up front closures
    • Adjustable drawstring crop hem
    • Runs true to size

    Style Number/Barcode: 06204-1709

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Darling Sleeveless Smocked Crop Top

    You'll adore styling this crop top with your favorite bottoms for any casual summer plans! The top is made from a woven fabric adorned with a square neckline, flirty ruffled shoulder straps, and a stretchy smocked bodice with a cropped hem for flaunting your figure. Complete the look in women's best-selling bottoms for the cutest outfit!

    Fit & Features

    • Woven fabric
    • Ruffled shoulder straps
    • Square neckline
    • Stretchy smocked bodice
    • Cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2509

    Category Name: Vacation Looks

    Price: $22.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bold New Look Corset Lace-Up Linen Skater Dress

    Make a bold impression in this corset linen skater dress all season long! The sweetheart neckline with a bust tie and adjustable straps provides a flattering fit while the flexible boning supports your shape. The strappy lace-up back adds a touch of playfulness to the skater silhouette and short-length hem. Complete the look in wedge sandals and a handbag.

    Fit & Features

    • Linen blend fabric lined with stretchy knit
    • Sweetheart neckline with bust tie
    • Adjustable straps, side zipper and hook-eye closure
    • Strappy lace-up back
    • Flexible boning
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3791

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Good Times Bodycon Abstract Print Mini Dress

    A mini dress that calls for good times only at casual parties or weekend plans! Designed with an alluring abstract print on mesh fabric, this dress is both chic and versatile. The sleeveless crew neckline and bodycon silhouette highlight your curves, while the side ruched seams flatter your figure. Complete the look with a mini shoulder bag and heels.

    Fit & Features

    • Abstract print
    • Mesh fabric, sewn-in knit lining, stretchy
    • Side ruched seams
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5606

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovely In Eyelet A-Line Mini Dress

    Make a lovely impression in this eyelet A-line mini dress at bridal showers or brunch with the girls! 

    Fit & Features

    • Eyelet lace fabric, stretchy knit lining
    • Strapless neckline
    • A-line silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5997

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sittin Pretty Tie Waist Wide-Leg Palazzo Pants

    Sit pretty in these high-rise palazzo pants to elevate your workwear or weekend wear! The chic pants offer a tie-waist design to snatch your waistline and a flattering wide-leg silhouette on breezy woven fabric. Complete the look in a bodysuit and mules.

    Fit & Features

    • Woven fabric
    • Tie-waist design
    • Back zipper closure
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1384

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Escape Tropical Print Tie-Front Top

    Escape to your dream vacay in this tropical print tie-front top offering flowy short sleeves and a cropped, relaxed fit. Style with the matching palazzo pants and your fave sandals.

    Shop Matching Bottoms: Sunny Escape Tropical Print Palazzo Pants

    Fit & Features

    • Woven fabric
    • Tropical print
    • Plunging V-neckline
    • Flowy short sleeves
    • Tie-front design
    • Cropped hem, relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-000002

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MULTI

    Available Size: S, M, L

    Product Badge:
    • Sale
  • So Effortless Ribbed Knit Bodycon Midi Dress

    This bodycon midi dress is the perfect blend of effortless and chic! Designed with a stretchy ribbed knit fabric for that comfortable fit, this mid-length dress features a trendy sleeveless square neck and back design with thin tank shoulder straps. The ribbed design on the body-hugging silhouette will flaunt your gorgeous figure. Layer on a faux leather jacket and pair with ankle booties for a night out!

    Fit & Features

    • Stretchy ribbed knit fabric
    • Sleeveless square neck and back
    • Tank straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5585

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunny Escape Tropical Print Palazzo Pants

    Escape to your dream vacay in these tropical print palazzo pants offering a high-rise waist and a flowy, wide-leg silhouette. Style with the matching tie-front top and your fave sandals.

    Shop Matching Top: Sunny Escape Tropical Print Tie-Front Top

    Fit & Features

    • Woven fabric
    • Tropical print
    • High-rise waist, front button and hidden zipper closure
    • Pleating
    • Wide-leg fit
    • Relaxed silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000002

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Note To Self Ribbed Knit A-Line Mini Dress

    Note to self, this sleeveless mini dress is a must-have for every day! Perfect for any occasion, this stretchy ribbed knit dress will surely become a staple in your wardrobe. It features a crew neckline with tank straps and a flattering A-line silhouette with a flirty front slit on the mini-length hem. Complete the look with an oversized blazer and a sleek necklace.

    Fit & Features

    • Soft and stretchy ribbed knit fabric
    • Crew neckline
    • Tank shoulder straps
    • Front slit
    • A-line fit
    • Runs true to size

    Style Number/Barcode: 05102-5632

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Chic Belted Trouser Shorts With Linen

    You'll be looking chic for the season in these lightweight linen-blend trouser shorts with a belted waist design. Style with the matching blazer for an elevated weekend vibe!

    Shop Matching Blazer: Looking Chic Blazer With Linen

    Fit & Features

    • Linen-blend woven fabric, smooth woven lining, no stretch
    • High-rise waist, belted design
    • Dual front pockets
    • Pleating
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06303-0299

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hidden Treasure Lace-Up Shell Accent Midi Dress

    Discover your new signature look with this irresistible midi dress featuring a unique shell accent neckline,  lace-up back offers undeniable allure, and a sultry side slit creates movement.

    Fit & Features

    • Texture knit fabric, moderate stretch, stretchy knit lining
    • V-neckline with shell accent trim
    • Spaghetti straps
    • Lace-up back
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6119

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Love Eyelet Knit Mini Dress

    You'll fall in love with the effortless summer vibes of this eyelet knit mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, a form-hugging fit, and a pretty floral eyelet pattern. The lined knit fabric offers plenty of stretch for comfortable wear. Style with strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length hem
    • Form-hugging fit
    • Floral eyelet pattern, knit fabric, knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5113

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Art Of Patchwork Crop Denim Jacket

    Layer on this retro-fab denim jacket for springtime fun! Showcasing a 60s-inspired patchwork design, this jacket offers a modern crop silhouette, slouchy long sleeves with button cuffs, a classic collar neckline, faux flap pockets, and button-down front closures for multiple styling options. Complete the look in a denim midi skirt to rock a denim-on-denim outfit!

    Fit & Features

    • Patchwork design
    • Non-stretch denim fabric
    • Button-down front
    • Faux flap pockets
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06203-0521

    Category Name: Vacation Looks

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vintage Charm Gingham Slit Peasant Maxi Skirt

    Vintage charm is yours with this gingham peasant maxi skirt showcasing a modern high front slit for effortless movement! 

    Fit & Features

    • Gingham print, woven fabric
    • High-rise elasticized waist
    • High front slit
    • Flowy ruffled maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 06301-000002

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Totally Crushing A-Line Mini Dress

    A crush-worthy strapless mini dress you'll love styling for every occasion! You'll love the flattering A-line fit, while the ruffled mini hem adds a touch of playful charm.

    Fit & Features

    • Smooth knit stretchy fabric
    • Strapless neckline
    • A-line silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000115

    Category Name: Vacation Looks

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: In Stock

    Available Color: SAGE

    Available Size: M

    Product Badge:
    • Sale
  • Tea Time Ruffled Short Skater Dress

    It's time for afternoon tea and this skater dress will make an adorable entrance! Get ready to sashay in this dress featuring a ruffle trim square neckline and tiered ruffled short-length hem to add a playful touch to the skater silhouette. And with adjustable spaghetti straps and a stretchy smocked bodice, you'll be comfortable all day. Complete the look in chic wedges and a flouncy hat.

    Fit & Features

    • Woven fabric lined with woven fabric
    • Ruffle trim neckline
    • Adjustable spaghetti straps
    • Stretchy smocked bodice
    • Tiered ruffled short-length hem
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3059

    Category Name: Vacation Looks

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine And Good Time V-Neck Mermaid Maxi Dress

    This mermaid maxi dress is here for sunshine and good times! Made from textured mesh fabric, this dress will have you feeling so cute. Features a flattering V-neckline, dual spaghetti straps, a crisscross back, and a bust cutout. The mermaid silhouette and high front slit accentuate your curves, while the maxi-length hem adds a touch of chicness. Complete the look with sandals and sunglasses!

    Fit & Features

    • Textured mesh fabric, stretchy knit lining
    • Dual spaghetti straps
    • V-neckline
    • High front slit
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5690

    Category Name: Vacation Looks

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Real Babe High-Rise Denim Skort

    Bring real babe energy in this high-rise denim skort perfect for casual, everyday styling! With a bodycon fit and shorts bottom for coverage, this skort will be the one you reach for.

    Fit & Features

    • Dark wash denim
    • High-rise waist
    • Front button and hidden zipper closure
    • Bodycon silhouette
    • Mini-length hem
    • Shorts bottom
    • Runs true to size

    Style Number/Barcode: 06603-0443

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • My Main Chic V-Neck Ruched Midi Dress

    Ultra-flattering and soft, this sleeveless midi dress will be your main chic style! The knee-length dress is designed with a classic V-neckline, spaghetti straps, side ruched seams, and a bodycon silhouette that shows off your curves on smooth-lined knit fabric. Complete the look with stiletto heels for a birthday brunch or bridal shower!

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Midi-length hem
    • Lined smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5479

    Category Name: Vacation Looks

    Price: $6.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free