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.

  • Three Pack Lace Detail Face Masks

    Stay safe while also showcasing an adorable look in these lace detail face masks! The set features three face masks with a pretty floral lace detail in the shades blush pink, black, and red. Pair these face masks with a basic bodysuit and denim for a cute everyday look.

    Fit & Features

    • Three pack of face masks
    • Floral lace detail
    • Shades of blush pink, black, and red
    • Earloops
    • This is not a medical-grade mask nor is a substitute for medical-grade equipment
    • Wash before and after use is recommended
    • Please consult local health authority for guidance on the use of non-medical grade masks

     

    Face masks are final sale merchandise and may not be returned or exchanged.

    Style Number/Barcode: 07305-0234

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Two Pack Cozy Socks

    Keep your at-home loungewear look cute and cozy in these adorable socks! The set features two pairs of cozy socks in a solid black and mocha hue. Pair these socks with your fave fuzzy slippers for the perfect comfy vibe!

    Fit & Features

    • Two pack set
    • Above the ankle design
    • Cozy material
    • Black and mocha hues

    Style Number/Barcode: 07306-0071

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sequin and Lace Face Mask

    Stun in a lace face mask that brings glamour to your formal evening outfits. The face mask features a floral lace design adorned with shimmering sequins throughout. Complete your look with a formal velvet dress.

    Fit & Features

    • Floral lace pattern
    • Sequins
    • This is not a medical-grade mask nor is a substitute for medical-grade equipment
    • Wash before and after use is recommended
    • Please consult local health authority for guidance on the use of non-medical grade masks

     

    Face masks are final sale merchandise and may not be returned or exchanged. 

    Style Number/Barcode: 07305-0228

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek And Sultry Bodycon Ruffle Mini Skirt

    Sleek and sultry, this bodycon ruffled mini skirt makes the perfect instant outfit with the matching top! 

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • High-rise waist
    • Side ruched seams
    • Bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

     

    Shop The Matching Top: Sleek And Sultry Tie Front Crop Top

    Style Number/Barcode: 06501-000045

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dainty Love Rhinestone Script Necklace

    Show off your love in a cute necklace that is too adorable! Style this necklace with a long sleeve dress for your next date night. The necklace features a dainty chain, a rhinestone embellished "Love" script accent. 

    Fit & Features

    • Dainty chain
    • Rhinestone embellished script accent
    • Lobster clasp closure
    • Gold version is 18 K Gold dipped
    • Silver version is Rhodium dipped

    Style Number/Barcode: 07002-0544

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Getaway Duffel Bag

    Treat yourself to a getaway with the girls and pack all of your essentials in a glam duffel bag! Pair this bag with your fave faux fur coat and booties.

    Black Glitter Bag

    • Top zipper closure with top faux leather handles
    • Detachable adjustable shoulder strap
    • Zippered exterior pocket
    • Single zippered pocket and two pouches on the interior
    • Gold metal purse feet at the bottom
    • Exterior is composed of combination PU material and polyester backing
    • Woven nylon lining


    Holographic Bag

    • Top zipper closure with two handles
    • Detachable shoulder strap
    • Clear Holographic body
    • Gold metal purse feet at the bottom
    • PVC-like material

    Style Number/Barcode: 07203-0404

    Category Name: Vacation Looks

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rhinestone Lanyard Keychain

    Make sure you always have your keys on you with this adorable lanyard keychain! It features a rhinestone adorned strap you can wear with a keychain attached. Add this to your wishlist for this holiday season!

    Fit & Features

    • Rhinestone adorned strap
    • Attached keychain

    Style Number/Barcode: 07308-0137

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tie Dye Crew Socks

    Add a fun and trendy vibe to your everyday 'fit with these crew socks! They feature an above the ankle fit with an allover tie dye print. Pair these socks with your fave pair of chunky sneakers.

    Fit & Features

    • Above the ankle fit
    • Allover tie dye print

    Style Number/Barcode: 07306-0073

    Category Name: Vacation Looks

    Price: $3.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Vibes Button Down Ribbed Mini Dress

    Rock a basic mini dress to layer with your favorite denim jacket or moto jacket this season. The dress features a crew neckline, a button-down front, long sleeves, and a mini length silhouette with a raw edge hem. The dress is composed of a ribbed knit fabric.

    Fit & Features

    • Crew neckline
    • Button-down front
    • Long sleeves
    • Mini length silhouette, raw edge hem
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch

    Style Number/Barcode: 05102-0955

    Category Name: Vacation Looks

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stay Chic Printed Tights

    Stay effortlessly chic by pairing these printed tights with your fave sweater dress! It features a high rise banded waist with a sheer unlined fabric that showcases an allover double O-print. Style these tights with some heeled booties for a date night out with bae.

    Fit & Features

    • High rise banded waist
    • Sheer, unlined fabric
    • Allover double O-print

    Fashion tape, adhesive bras, adhesive panties, pasties, hosiery, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07306-0074

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dainty Layered Rhinestone Necklace

    Encircle yourself in a dainty layered necklace to accent your casual outfits. The necklace features a layered two-row design, a rhinestone accent, and a circle outline embellished with mini rhinestones. 

    Fit & Features

    • Two-row layered design 
    • Rhinestone accent 
    • Circle outline embellished with mini rhinestones
    • Dainty chain 
    • Lobster clasp closure  

    Style Number/Barcode: 07002-0598

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rhinestone Butterfly Buckle Clear Belt

    Create stunning looks in this gorg butterfly buckle belt! It features a clear design with a rhinestone embellished statement butterfly buckle. Pair this belt with light wash denim and a basic tee to elevate an everyday 'fit.

    Fit & Features

    • Clear belt
    • Rhinestone embellished butterfly buckle

    Style Number/Barcode: 07301-0226

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fierce and Basic Two Pack Belt Pack

    Go fierce or keep it basic with a belt to tie your look together! The pack includes two belts that feature a mini-double o-ring buckle. The sleek black belt is composed of faux leather material. The leopard print belt is composed of a faux suede and faux leather combination. Complete look with a basic bodysuit and jeans.

    Fit & Features

    • Pack includes two belts
    • Double O-ring design
    • Black faux leather belt
    • Leopard print faux leather and faux suede belt
    • Adjustable 

    Style Number/Barcode: 07301-0223

    Category Name: Vacation Looks

    Price: $6.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leopard Print Face Mask With Earloops

    Update your look with a fierce face mask! The face mask features a leopard print design, earloops for a customized fit. Pair this face mask with your basic everyday 'fit to give it a trendy vibe.

    Fit & Features

    • Allover leopard print
    • Earloops
    • This is not a medical-grade mask nor is a substitute for medical-grade equipment
    • Wash before and after use is recommended
    • Please consult local health authority for guidance on the use of non-medical grade masks

    Face masks are final sale merchandise and may not be returned or exchanged.

    Style Number/Barcode: 07305-0192

    Category Name: Vacation Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stunning And Sultry Sweetheart Mini Dress

    Create a stunning and sultry look in this gorgeous sweetheart mini dress! It features a sleeveless bodice with spaghetti straps, a mini length silhouette and a curve-hugging fit. Pair this dress with a faux leather jacket for a girl's night out.

    Fit & Features

    • Spaghetti straps
    • Sweetheart neckline with seam detailing at the bust
    • V back
    • Short, form-hugging fit
    • Ribbed knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1039

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Sleeveless Ruched Mini Dress

    Create a sleek impression in this mini dress to stun on your next night out! The dress features a sleeveless square neckline, tank-like straps, ruched side seams, and a mini length silhouette. Complete look with a chunky statement necklace

    Fit & Features

    • Sleeveless square neckline
    • Tank straps
    • Ruched side seams
    • Smooth knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1045

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Faux Leather Snake Print O Ring Belt

    Keep it sleek in a snake print belt to elevate your look! The belt features a faux leather material, a trendy snake print, and a double O ring buckle. Complete look with a pair of high waist jeans.

    Fit & Features

    • Faux leather
    • Snake print
    • Double O-Ring buckle
    • Adjustable 

    Style Number/Barcode: 07301-0221

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Girlycore Floral Puff Sleeve Crop Top

    Channel a cute girlycore vibe with this floral puff sleeve crop top! Detailed with a dainty floral print, this top features a sweetheart neckline, a ruched bust with an adjustable drawstring, adorable short puff sleeves, a smocked back for added stretch, and a cropped hem with a flirty ruffled trim. Style with high-rise jeans and sandals.

    Fit & Features

    • Dainty floral print
    • Woven fabric, front knit lining, minimal stretch
    • Sweetheart neckline, ruched bust with adjustable drawstring
    • Short puff sleeves, elastic cinched hems
    • Smocked back
    • Ruffled cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2533

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: L, XL

    Product Badge:
    • Sale
  • Twisted Rhinestone Hoop Earrings

    Add a glam touch to your look with these glitzy rhinestone hoop earrings! They feature a large hoop earring with a twisted rhinestone design. Pair these hoops with a basic tee and distressed denim to elevate your everyday casual 'fit.

    Fit & Features

    • Large hoop earring
    • Twisted rhinestone design

     

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

    Style Number/Barcode: 07001-0417

    Category Name: Vacation Looks

    Price: $4.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Honey Sheet Mask

    Nourish skin with a face mask that moisturizes and leaves skin feeling so hydrated. The sheet mask features a honey essence. Complete your pamper session with a fab cozy matching set.

    Fit & Features

    • Sheet mask
    • Honey essence 

    Style Number/Barcode: 07307-0052

    Category Name: Vacation Looks

    Price: $1.97 $4.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Double Strap Basic Crop Top

    This crop top is just what your basics collection is missing! This essential top that goes with everything features a flattering scoop neckline, sexy thin double straps, a V strap accent at the back, and a cropped hem. The top is composed of a knit fabric that offers a relaxed fit with a moderate stretch. We love to dress it up with denim and heels for GNO.

    Fits & Features

    • Scoop neckline 
    • Thin double straps 
    • V Strap back
    • Cropped hem 
    • Knit fabric
    • Relaxed fit 
    • Moderate stretch 

     

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06001-2803

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Faux Wool Banded Boater Hat

    Add a trendy vibe to your fall and winter 'fit with this chic boater hat! It features a traditional boater design with a stylish ribbon band. Wear this hat with a chunky knit sweater and thigh-high boots.

    Fit & Features

    • Traditional boater design
    • Ribbon band
    • Faux wool material

    Style Number/Barcode: 07302-0260

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off The Shoulder Ribbed Knit Cutout Mini Dress

    Stun in a mini dress that brings sultry appeal with cutout details! The mini dress features an off the shoulder neckline, cutout detail at the bust with matching cutout detail at the midriff, and a mini length silhouette. Complete look with clear mules.

    Fit & Features

    • Off the shoulder neckline 
    • Cutout detail at the bust
    • Cutout detail at the midriff
    • Long sleeves
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0864

    Category Name: Vacation Looks

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Twist Knot Open Back Ribbed Mini Dress

    Stun in a dress that makes them take a double-take with bold details! The dress features a crew neckline, fitted long sleeves, and a stunning open back with a twist knot bar strap accent. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules

    Fit & Features

    • Crew neckline
    • Fitted long sleeves
    • Open back 
    • Twist knot bar strap 
    • Ribbed knit fabric
    • Mini length silhouette
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0991

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance