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.

  • Trendy Girl Next Door Slip Dress

    Show off your trendy style in this adorable cow print slip dress! It features a sleeveless V-neckline, bungee spaghetti straps, a stylish small front slit, and a short fitted silhouette. Complete the look with ankle booties.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Short front slit
    • Mini-length fitted silhouette
    • Brushed knit fabric, moderate stretch
    • Cow print
    • Runs true to size

    Style Number/Barcode: 05102-4325

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lots To Love Heart Hoops

    There's lots to love about these heart-shaped hoops! With omega back closure. Complete the look in a stylish denim jacket.

    Fit & Features

    • Heart-shaped hoops
    • Omega closure
    • Metal material

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-1175

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Ella Distressed Mom Jeans

    Stay on-trend in the Ella Distressed Mom Jean perfect for dressing up or down! They feature a high-rise waist, distressed accents on the front, a stylish mom leg, and a cropped frayed hem. The medium-wash denim fabric offers no stretch. Complete the look in a graphic top and sneakers for a casual fit.

    Fit & Features

    • High-rise waist
    • Mom style leg
    • Distressed front accents, crop frayed hem
    • Five-pocket and belt loop design
    • Front button and hidden zipper closure
    • Medium-wash non-stretch denim fabric
    • Runs true to size

    Style Number/Barcode: 06602-0246

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Queen Of Hearts Dainty Lariat Necklace

    You're the queen of hearts in this necklace design in a layered style with a choker and lariat chain with lobster clasp closure. Complete the look in a plunge neck bodysuit.

    Fit & Features

    • Dainty design
    • Heart charms
    • Layered-style
    • Choker and lariat chains
    • Lobster clasp closure

    Style Number/Barcode: 07002-1112

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Low-Key Glamour Ring Set

    Showcase low-key glamour and bring a subtle sparkle to your look with this dainty ring set. It features five rings with varying designs, including simple sleek bands with rhinestone embellishment, a single twisted band, and basic bands with glitzy glitter details. Style this set with stud earrings.

    Fit & Features

    • Set of five rings
    • Varying designs
    • Sleek bands, rhinestone embellishment
    • Twisted band
    • Basic bands, glitter details

    Style Number/Barcode: 07004-0252

    Category Name: Vacation Looks

    Price: $4.97 $11.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Head-Turning Chic Flocked Velvet Bodysuit

    Create a head-turning chic look with this sultry sheer mesh bodysuit. It features a mock neckline, long fitted sleeves, a cheeky bottom, and an all-over flocked velvet scroll pattern. Style this bodysuit with faux leather pants and clear mules.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Cheeky bottom, dual snap button closure
    • Form-hugging fit
    • Sheer mesh fabric, flocked velvet scroll pattern
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-3805

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Starburst Moon Charm Multipack Bracelet Set

    This four-pack bracelet set is perfect for creating a boho-chic look. It features starburst and moon charms with rhinestone insets on various chain-link designs each with lobster-clasp closure. Complete the look with trendy oversized shades.

    Fit & Features

    • Four-pack multipack set
    • Starburst, moon charms with rhinestones
    • Various chain-link designs
    • Lobster clasp closure 

    Style Number/Barcode: 07003-0325

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Follow Your Heart Bracelet Three Pack Set

    Follow your heart to this sparkly bracelet set featuring one heart charm, twisted snake chain, and delicate rhinestone drop charm each with lobster clasp closure. Complete the look in a chic blouse and jeans.

    Fit & Features

    • Rhinestone embellishments
    • Three pack bracelet set
    • One heart charm
    • One twisted snake chain
    • One rhinestone drop charm 
    • Lobster clasp closure

    Style Number/Barcode: 07003-0324

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Can't Live Without It Mini Skirt

    This chic skirt is the one staple piece you'll want to pair with all your favorite tops! The corduroy skirt features a high-rise waist, a front slit accent, and a mini, bodycon fit. Complete look with a bodysuit and lug boots. 

    Fit & Features

    • High rise waist
    • Front slit accent
    • Bodycon fit
    • Mini length hem
    • Lined corduroy fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06301-0128

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Reign In Charm Rhinestone Choker

    Reign this charming choker to add a glam touch to your outfit. It features a dainty chain-link with rhinestone embellishments and a lobster clasp closure. Complete the look in a silky satin blouse.

    Fit & Features

    • Dainty chain-link 
    • Rhinestone embellishments
    • Lobster clasp closure

    Style Number/Barcode: 07002-1129

    Category Name: Vacation Looks

    Price: $3.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dark Romance Crochet Mesh Bodysuit

    Bring the allure at night in this romantic crochet mesh bodysuit featured in short sleeves, a crew neck with dual snap and zipper closure. Complete the look in high-rise pants and heels.

    Fit & Features

    • Short sleeves, crew neck
    • Crochet applique 
    • Dual snap and zipper closure
    • Sheer mesh fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06001-3731

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Like A Daydream Lace Ruffle Skater Dress

    Arrive on the scene like a daydream in this lace skater dress with flirty ruffles and mini-length hem that'll get you all the compliments!

    Fit & Features

    • Lace knit fabric
    • Square neckline
    • Adjustable spaghetti straps
    • Skater silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4156

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Certified Lover Girl Baseball Cap

    Flaunt your status with this cute baseball cap featuring a script that reads, "Certified Lover Girl" on the front and a classic baseball cap design. Complete the look in a trendy puffer jacket for a coffee run.

    Fit & Features

    • Baseball cap design
    • Short brim
    • Script the reads "Certified Lover Girl"
    • Adjustable back strap

    Style Number/Barcode: 07302-0505

    Category Name: Vacation Looks

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Sparkle Heart Hoop And Huggies Six Pack Set

    Show your love for the sparkle in this six-pack earrings set! It features rhinestone hoops, heart-shaped hoops, solid hoops, and three various styles of huggies. Complete the look in a cute long sleeve top.

    Fit & Features

    • Six-pack earring set
    • One solid, heart-shape, rhinestone hoops
    • Three various styles of huggies
    • Omega and post-back closures
    • Metal materials 

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-1157

    Category Name: Vacation Looks

    Price: $6.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Special Price
  • Raise The Bar Rhinestone Layered Necklace

    Set the trend in this rhinestone layered necklace featuring a layered design with charm-bar accents and lobster clasp closure. Complete your look in a low-cut blouse.

    Fit & Features

    • Layered design
    • Dainty chains
    • Rhinestone charm-bar accents
    • Lobster clasp closure

    Style Number/Barcode: 07002-1174

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miss Python Mock Neck Cutout Crop Top

    In this snake print crop top, you've clearly won the fashion show! It features long sleeves, a mock neck,  and front cutout accents on a fitted hem. Composed of a soft knit fabric with a moderate stretch. Perfect for styling with paperbag shorts.

    Fit & Features

    • Long sleeves, mock neck
    • Front cutout accents
    • Fitted crop hem
    • Snake print
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-3796

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheer Allure Square Neck Bodysuit

    Bring the allure to your girl's night in this square neck bodysuit. Featuring long sheer mesh sleeves, a thong bottom with a dual snap-button closure, and a form-hugging fit. Complete the look in boyfriend jeans and heels.

    Fit & Features

    • Long fitted sheer mesh sleeves
    • Square neckline
    • Thong bottom, dual snap-button closure
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-3769

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lasso Of Style Faux Wool Boater Hat

    Unveil your country girl style with this faux wool boater hat! It features a braided rope with a tassel and a wide brim. Complete the look in a denim jacket.

    Fit & Features

    • Braided rope with tassel
    • Wide brim
    • Faux wool material

    Style Number/Barcode: 07302-0474

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Country Girl Faux Wool Rhinestone Panama Hat

    You're one glam country girl in this Panama hat featuring a rhinestone band, wide brim, and faux wool material. Complete the look in a chic shacket.

    Fit & Features

    • Rhinestone band
    • Wide brim
    • Faux wool material

    Style Number/Barcode: 07302-0477

    Category Name: Vacation Looks

    Price: $19.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready To Party Satin Wrap Skirt

    This satin mini skirt is ready for every party you're invited to this season! It features a high-rise waist, faux-wrap front, form-fitting silhouette, on satin fabric with minimal stretch. Complete the look in a sultry crop top and mules. 

    Fit & Features

    • High-rise waist
    • Faux wrap front
    • Form-fitting silhouette
    • Mini hem, zipper closure
    • Satin fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06501-0622

    Category Name: Vacation Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always On Point Plaid Suspender Skirt

    Make sure your 'fit is always on point with this chic plaid mini skirt. It features thin suspender straps, a high waist, and a short, curve-hugging fit with a small side slit. Style this skirt with a long sleeve bodysuit and your fave pair of booties.

    Fit & Features

    • Thin suspender straps
    • High waist
    • Mini-length, form-fitting silhouette
    • Side slit
    • Plaid print
    • Ponte knit fabric
    • Runs true to size

    Style Number/Barcode: 06501-0551

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Island Getaway Plunge Neck Tropical Jumpsuit

    In need of a vacay? This tropical print jumpsuit is just the ticket! It features long bishop sleeves, a plunge v-neckline, tie-waist, wide-leg silhouette on textured knit fabric with a moderate stretch. Complete the look in cute wedges.

    Fit & Features

    • Long bishop sleeves
    • Plunge v-neckline
    • Tie-waist, wide-leg silhouette
    • Tropical print
    • Textured knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06502-0848

    Category Name: Vacation Looks

    Price: $27.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Sophistication Tweed Cropped Jacket

    Bring the chic sophisticated vibes to your look with this on-trend tweed jacket. It features a collared neckline, long sleeves, a complete button-down front, and a cropped, form-hugging fit. Style this jacket with faux leather shorts and booties.

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Complete snap button-down front
    • Chest pockets
    • Cropped, form-hugging fit
    • Woven tweed fabric, smooth lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1098

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Night To Remember Cross Halter Bodycon Dress

    You're sure to remember the night looking so chic in this bodycon dress! It features a cross halter neckline with a keyhole accent, all-over ruching to accentuate your curves, and a mini-length hem. The dress is composed of a mesh-knit lined fabric with a moderate stretch. Complete the look in rhinestone hoops and stiletto heels.

    Fit & Features

    • Cross halter neckline
    • Keyhole accent
    • All-over ruching
    • Mini-length hem
    • Mesh-knit lined fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05103-4273

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free