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.

  • Butterfly Kisses Ring 10 Pack
    Keep the style going down to your finger tips! This set includes a variety of ten multi sized rings. They showcase chain link designs, a heart midi ring, and butterflies! Layer them up for a boho glam look!

    Style Number/Barcode: 07004-0029

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Satin Tie Front Kimono

    Designed with a satin fabric, a deep V neckline, quarter sleeves, and a cropped hem, this kimono tie front top is feeling like a new closet staple! Offering a relaxed fit, this satin blouse adds style to your look. Pair with high waist pants and you are good to go!

    Model is 5'8" with a 32" bust,  25" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0165

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fierce Leopard Sleeveless Midi Dress

    Get spotted in this sleek midi dress to make a fierce statement! It features sleeveless bodice, a cowl neckline, adjustable straps and a midi length silhouette. The all over leopard print is all you need to stay on trend. Dress is composed of a lined semi-sheer lightweight woven fabric that offers a relaxed fit with a minimal stretch. Includes a back zipper closure. 

     

    Style Number/Barcode: 05101-0352

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leopard Print Wrap Front Midi Dress

    You're quite the fierce fashionista, so this leopard print midi suits you! The dress features a sleeveless bodice, adjustable spaghetti straps, a wrap front V neckline, a V back with a hidden zipper closure, a high waist seam with a wrap front skirt with a faux tie detail, and a mid-length, flowy fit. Dress is comosed of a sheer textured woven fabric with a short woven lining.

    Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0396

    Category Name: Vacation Looks

    Price: $19.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • F*ck You Next Cap
    Ummmm NEXT! Send a straight forward message in a cap designed for a baddie. This  baseball cap that features front embroidered text and an adjustable back buckle closure.

    Style Number/Barcode: 07302-0117

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Textured Knit Cabby Hat
    Keep it classic with a vintage inspired cabby! it features a traditional cabby design with an elastic back for stretch and button details at the sides. Composed of a soft knit fabric.

    Style Number/Barcode: 07301-0078

    Category Name: Vacation Looks

    Price: $5.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rainbow Marquise Rhinestone Hair Pins
    Add a pop of color to that updo lady! This pack includes two hair pins that are bobby style and are varied shaped of marquise stones and circular stones.

    Style Number/Barcode: 07006-0100

    Category Name: Vacation Looks

    Price: $2.97 $6.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shell Choker Necklace
    This adorable shell choker is totally beach babe approved! The necklace features a row of seashells woven together with a single gold accent shell, and includes a gold adjustable chain and lobster clasp closure.

    Style Number/Barcode: 07002-0252

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Snake Print Ruffle Mini Dress
    Ruffle up the style game with this on trend snake print mini dress. It features a sleeveless bodice, adjustable spaghetti straps that lead to a halter back, a deep V neckline, and a high waist seam with a tiered, ruffled flowy skirt. The dress is composed of a chiffon fabric with a woven lining and has no stretch.

    Style Number/Barcode: 05101-0386

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Call Of The Wild Cross Body

    Answer the call as you slay with this fierce cross body! It features an envelope design with snap button closure, a large zippered compartment and a detachable shoulder chain strap. The body is composed of a faux suede material. The interior is composed of a nylon material and includes card slots. 

    Style Number/Barcode: 07201-0001

    Category Name: Vacation Looks

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Rise Slit Skinny Jeans

    Take on the day with these must have skinny jeans! They feature a high rise waist, a traditional five pocket with belt loop design, a single button with zipper closure, knee slit accents and a skinny leg fit with tapered leg. Jeans are composed of a stretchy denim fabric that offer a curve hugging fit.

    Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06602-0050

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bejeweled Headband
    Add some jewels to your look! This open ended headband features a knot accent at the center and is composed of a satin material. Headband is structured and has multi colored, multi sized stones throughout!

    Style Number/Barcode: 07006-0063

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pearl Embellished Headband
    Add a little to your look with a headband! This open ended band is composed of a knit material that sheen finish and has a sweet pearl accent off center with little touches of rhinestone.

    Style Number/Barcode: 07006-0062

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Parisian Girlie Wool Beret

    Add a pinch of Parisian chic to your wardrobe in this classic beret – ooh la la! Crafted from a soft and luxe wool-blend material with a classic beret design, this hat offers lasting beauty and warmth. Complete the look in a cute faux leather jacket for your next trip to Europe or inspired cafe!

    Fit & Features

    • Classic beret design
    • Wool-blend material
    • Soft and comfortable

    Style Number/Barcode: 07302-1540

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Waist Destructed Shorts
    Oasis by Eunina

    Freshen up your spring wardrobe with this pair of high waist destructed shorts! The white denim bottoms feature a high rise waist, the traditional five pocket and belt loop design, a front button and hidden zipper closure, distressed detailing down the front, and a cuffed hem. The shorts offer moderate stretch and a form-fitting style.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 06603-0761

    Category Name: Vacation Looks

    Price: $4.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tortoise Shell Hair Clips
    Step up your hair accessory game with these trendy tortoise shell hair clips! The set features two alligator style clips, one with an open accent.

    Style Number/Barcode: 07006-0070

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Take Me To The Edge Cropped Jeans

    Give your look an edge of attitude with these must have jeans! They feature a high rise waist, a single button with zipper closure, a traditional belt loop with five pocket design, and a skinny leg fit with heavy distressed detailing and slits throughout. Jeans are composed of a denim fabric that offers a curve hugging fit with a moderate stretch.

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06602-0046

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrap Around My Heart Dress

    You're looking like hot stuff this evening, babes! This dress has a wrap bodice with a deep V neckline, spaghetti straps, and ruching on the side. A wrap skirt creates an asymmetrical hemline for a party perfect ensemble. Dress is composed of an unlined crepe fabric that offers a moderate stretch.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05103-3609

    Category Name: Vacation Looks

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Snake Print Long Sleeve Crop Top

    Strut in snake print! This crop top features a deep v neckline, long sleeves that puff at the wrist and a tie front closure. It is composed of a semi sheer chiffon material that showcases a neutral snake print design. Top offers a relaxed fit.

     

    Model is 5'9" with a 32" bust, 24.5" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0247

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • On A Mission Bikini Bottom
    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

    You're on a mission to kick it beachside! This swim bottom features a high rise fit, open sides with large gold metal grommets and tie straps, and a full coverage bottom. 

    Model is 5'9 with a 33" bust, a 24" waist, and 35.5" hips. She is wearing a size small.

    Style Number/Barcode: 07105-0022

    Category Name: Vacation Looks

    Price: $15.87 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Don't Cross Me Anklet Set

    This set includes two sleek designed toe rings that are open ended, as well as a dainty chain anklet with two rows and cross charms that dangle and reflect with the help of the dazzling rhinestones! Anklet has a lobster clasp closure and is adjustable in size.  

    Style Number/Barcode: 07003-0028

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Buttoned Beauty Ribbed Mini Dress

    Button up in this cute mini for the perfect day out! It features an off the shoulder neckline, a multi button down front, fitted long sleeves and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a curve hugging fit with a moderate stretch. 

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

     

     

    Style Number/Barcode: 05102-0272

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Josie Mid Rise Skinny Jeans

    Oasis By Eunina

    Introducing your new favorite skinnies. These jeans feature a high waist, zip fly, 5-pocket styling and light destruction detail. They're made of a stretchy denim and have a body-hugging fit.

    Style Number/Barcode: 06602-0004

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Staple Strap Sandals

    Make these sandals a staple to your closet! The simple design features a single strap as well as an adjustable ankle strap with a gold hued buckle closure. They also feature a chain detailing around the edge of the foot. They are composed of a faux leather material that makes them work with any outfit!

    Style Number/Barcode: 07404-0026

    Category Name: Vacation Looks

    Price: $12.97

    Availability: Out of Stock

    Product Badge:
    • Ships Free