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.

  • Romance Rules Lace-Up Lace Tunic Top

    Get swept off your feet with the romantic allure of this lace tunic top, designed with a pretty lace-up front and flowy silhouette with a cute ruffle trim.

    Fit & Features

    • Sheer lace fabric, bust knit lining
    • V-neckline, adjustable spaghetti straps
    • Lace-up front design
    • Flowy silhouette
    • Ruffled trim, open front slit design
    • Longline hem
    • Runs true to size

    Style Number/Barcode: 06003-000285

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: S

  • Breezy Weekend Short Sleeve Button Up Denim Romper

    From coffee shops to running errands, you'll live in this sweet denim romper all weekend! With its collar neckline, form-hugging fit, and short-length hem, this short sleeve romper is perfect for any adventure. And with flap pockets and button-up front closures, you can keep stylish. Complete the look with flat sandals and a crossbody bag!

    Fit & Features

    • Denim fabric, minimal stretch
    • Collar neckline
    • Button-up front closures
    • Flap pockets
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0383

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready For Anything Puffer Tote Bag

    Versatile and ready for anything, this puffer tote bag keeps your essentials organized and your look on-trend! It's designed with top handles and an adjustable crossbody strap for versatile wear. The top snap-button closure leads to a spacious and lined interior with side pockets to hold your phone or other loose items and a secure zipper pocket perfect for stashing cash or cards. Complete the look in a casual jumpsuit or romper for weekend plans or travel!

    Fit & Features

    • Insulated puffer material
    • Top handles
    • Adjustable crossbody strap
    • Top snap-button closure
    • Spacious interior, lined, three pockets

    Style Number/Barcode: 07203-2003

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Enchanting Charm Butterfly Rhinestone Lariat Necklace

    Add an enchanting charm to your look with this pretty butterfly rhinestone lariat necklace! It features a two-row design with a rhinestone chain layer and a dainty ball chain layer accented with a rhinestone-embellished butterfly charm, a cascading ball chain lariat, and a sleek rhinestone-adorned bar charm. Style with a chic ring set.

    Fit & Features

    • Two-row layered design
    • Rhinestone chain layer
    • Ball chain layer
    • Rhinestone-embellished butterfly charm
    • Ball chain lariat, rhinestone-embellished bar charm
    • Back adjustable chain with lobster clasp closure

    Style Number/Barcode: 07002-1766

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    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:
    • Sale
  • 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
  • Bloom Baby Flower Claw Clip Set

    Hair game = bloomin’ cute. These floral claw clips bring the vibe, whether you're going for soft girl sweet or Y2K realness—just clip and go.

    Fit & Features

    • Durable material with a glossy finish
    • Bold floral design with petal detail
    • Claw grip closure 

    Style Number/Barcode: 07006-000187

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: MULTI-2

    Available Size: NS

    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
  • 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
  • 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: $6.97 $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
  • Breezy Sheer Lace Tie-Front Top

    Cute and breezy, this sheer floral lace top features a V-neck with a tie-front design and long fitted sleeves with flared hems. Style with denim shorts and sandals for a casual summer look.

    Fit & Features

    • Sheer textured floral lace fabric
    • V-neckline
    • Tie-front design
    • Long fitted sleeves, flared hems
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06202-000029

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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