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.

  • Comfy-Chic One Sleeve Top

    Style up this comfy-chic top to take your loungewear style up a notch! It features a stylish one sleeve and a relaxed, loose fit with a mid-length ribbed banded hem. Pair this top with biker shorts and gold hoop earrings.

    Fit & Features

    • One-shoulder neckline with elastic ribbed detailing
    • Long puffy sleeve
    • Relaxed, loose fit
    • Mid-length banded hem
    • French terry knit fabric, moderate stretch

    Style Number/Barcode: 06002-0575

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping Knit Classy Sleeveless Mini Dress

    Class up your basic mini dress with details that stand out! The dress features a sleeveless crew neckline, dramatic shoulder pads, and a mini length silhouette. The dress is composed of a cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with chunky sneakers for a casual vibe.

    Fit & Features

    • Crew neck
    • Sleeveless bodice
    • Shoulder pads
    • Mini length silhouette
    • Cotton knit fabric
    • Relaxed fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1033

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romance Forever V-Neck Bow Floral Lace Top

    Romance your look with this floral lace top boasting a delicate satin bow and sheer bodice that flaunts your figure.

    Fit & Features

    • Floral lace fabric, bust knit lining
    • V-neckline, satin bow
    • Adjustable spaghetti straps
    • Sheer bodice
    • Fitted mid-length hem
    • Runs true to size

    Style Number/Barcode: 06001-000008

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dare To Layer Denim Jacket

    Layer up this season in a denim jacket to create those casually chic vibes! The jacket features a collared neckline, a multi-button down front, two chest pockets, and long sleeves that can be cuffed. Layer with a mini dress and ankle booties. 

    Fit & Features

    • Collared neckline
    • Multi-button down front
    • Two chest pockets
    • Long sleeves with buttoned cuff
    • Light-medium wash denim fabric
    • Mid-length fit

    Style Number/Barcode: 06203-0068

    Category Name: Vacation Looks

    Price: $15.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curves Ahead Sleeveless Ruched Midi Dress

    Showcase curves in a ruched midi dress that elevates your night-out look! The dress features a sleeveless mock neckline, a ruched body, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit and a moderate stretch. Complete the look with clear mules.

    Fit & Features

    • Sleeveless mock neckline
    • Ruched body
    • Midi-length silhouette
    • Smooth knit fabric, knit lining
    • Form-hugging fit
    • Moderate stretch
    • Style runs small

    Style Number/Barcode: 05101-0956

    Category Name: Vacation Looks

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ribbed Knit Crew Neck Bodycon Mini Dress

    Keep it casually chic in a mini dress that is a total must-have! The short dress features a crew neckline with a racerback design, a mini-length hem, and is composed of a form-hugging ribbed knit fabric. Put your hair in an updo and style with strappy mules for a cute look!

    Fit & Features

    • Crew neckline
    • Sleeveless bodice 
    • Racerback design
    • Mini-length hem
    • Ribbed knit fabric, fully lined 
    • Form-hugging fit, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-0689

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shimmering Beauty Rhinestone Necklace And Earrings Set

    You'll be a stunning shimmering beauty in this necklace and earring set! The pack features a choker necklace with two rows of rhinestones and matching stud earrings. Pair this set with a simple tee to add some glam to your everyday look.

    Fit & Features

    • Choker necklace and stud earrings set
    • Two row rhinestone choker
    • Rhinestone stud earrings

     

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

    Style Number/Barcode: 07002-0524

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On That Basic Open Back Sleeveless Catsuit

    Channel those basic vibes in a catsuit that can be dressed up for a casual day out. The catsuit features a sleeveless square neckline, spaghetti straps, and a partially open back. The relaxed fit bodice leads to a skinny leg fit with a tapered hem. Style your catsuit with chunky sneakers for a casual low-key outfit.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Partially open back 
    • Skinny leg fit with a tapered hem
    • Smooth knit fabric,
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0464

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Booked Halter Skater Mini Dress

    This breezy mini dress will inspire you to book a vacay somewhere sunny with an ocean view! With a flattering halter neckline and playful ruffled skater silhouette, this dress is perfect for any getaway.

    Fit & Features

    • Airy woven fabric, stretchy knit lining
    • Halter neckline with spaghetti strap ties
    • Stretchy smocked back, zipper and hook-eye closure
    • Ruffled skater silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4038

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Picture Perfect Open Back Ruched Mini Dress

    Create a pic-worthy moment in this bold dress that brings all the details! Style with stilettos for your next night out in this ruched mini dress! The dress features a crew neckline, a head-turning open-back design, and a ruched body. 

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Open back with bar strap tie 
    • Ruched body
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05101-0888

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Totally Chic Ruched Knit Mini Dress

     Keep it totally chic in a ruched mini dress! The dress features an off the shoulder neckline, long fitted sleeves, and a ruched drawstring center. The dress is composed of a ribbed knit fabric that hugs curves in all the right places. Complete look with sneakers for a casual look. 

    Fit & Features

    • Off the shoulder neckline
    • Long fitted sleeves
    • Ruched drawstring center
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0932

    Category Name: Vacation Looks

    Price: $14.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In Knit To Win It Midi Dress

    You'll be totally in it to win it in this adorable knit midi dress! It features a double-lined knit fabric and a mid-length, curve-hugging silhouette. Wear this dress with chunky sneakers for an adorable everyday look.

    Fit & Features

    • Spaghetti straps
    • Scoop neckline
    • Mid-length form-hugging fit
    • Double lined knit fabric

    Style Number/Barcode: 05102-0877

    Category Name: Vacation Looks

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slaying Knit Sleeveless Ribbed Midi Dress

    Slay it in a ribbed knit dress that stuns for your next date night in! The dress features a sleeveless square neckline, sleek bungee straps, and a curve-hugging midi-length silhouette. Complete look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0964

    Category Name: Vacation Looks

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Chic Tie Front Crop Top

    Create a chic moment in this crop top! The top features a plunging tie front bodice, long sleeves with buttoned cuffs, and a cropped hem. Complete look with jeans. 

    Fit & Features

    • Plunging tie-front bodice
    • Long sleeves with buttoned cuffs
    • Cropped hem
    • Lightweight woven fabric
    • Relaxed fit 

    Style Number/Barcode: 06204-0385

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's A Showstopper Ruched Midi Dress

    Make them stop and stare at this stunning dress that commands attention! The sleek midi dress features a trendy square neckline, sleek bungee straps, and a curve-hugging ruched midi silhouette. Complete your look with duster earrings for your night-out outfit.

    Fit & Features

    • Sleeveless square neckline, bungee straps
    • Strapless bra recommended
    • Side ruched detailing
    • Midi-length bodycon silhouette
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0848

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slay Every Day Basic Scoop Neck Midi Dress

    Slay every day in a basic midi dress that is effortlessly chic. The dress features a sleeveless scoop neckline, tank-straps, and a midi length silhouette. The double lined smooth knit fabirc offers a comfortable feel. Complete your look with chunky sneakers and stud earrings to nail low-key vibes.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank-straps
    • Midi length silhouette
    • Double lined smooth knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0908

    Category Name: Vacation Looks

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Clear and Chic Lucite Low Block Heels

    Stay clearly chic in heels that stun for your brunch date! The heels feature an open square toe, a double row of clear straps, and lucite block heel. Complete your look with a ribbed midi skirt and bodysuit. 

    Fit & Features

    • Open back 
    • Open square toe
    • Double row of clear straps
    • Lucite block heel 

    Style Number/Barcode: 07401-2462

    Category Name: Vacation Looks

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Adore You Metal Leaf Earrings

    Feel adored in these earrings that add a chic touch to your date night outfit. The earrings feature a metal leaf design with reflective wave detail. Complete your outfit with a sleek jumpsuit and mules. 

    Fit & Features

    • Metal
    • Leaf design
    • Wave detail

     

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

    Style Number/Barcode: 07001-0691

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Two Pack Iridescent Gemstone Hair Clips

    Brighten tresses with glitzy hair clips! Use the clips to create gorgeous side parts or fab updos for your next night out! The pack includes two large snap clips adorned with mini iridescent gemstones. Complete your look with a sleek jumpsuit and mules to create a stunning date night outfit. 

    Fit & Features

    • Pack includes two clips
    • Snap closure 
    • Mini iridescent gemstones

    Style Number/Barcode: 07006-0114

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In Knit For A Good Time Basic Mini Dress

    Throw on this basic mini dress and let the good vibes flow! This knit dress is perfect to dress up or dress down for your next date night or for GNO with the squad. The dress features a trendy square neckline, sleek bungee straps, and a mini-length silhouette. Dress up with mules or keep it casual in sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0873

    Category Name: Vacation Looks

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Ribbed Knit Basic Mini Dress

    Basic yet still so chic, this ribbed knit mini dress is an everyday essential! It features a doubled ribbed knit fabric for comfortable wear and a form-hugging fit to enhance your curves. Pair this adorable dress with some chunky sneakers to get that effortless vibe.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Doubled ribbed knit fabric

    Style Number/Barcode: 05102-0841

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dainty Layered Bar Charm Lariat Necklace

    Polish your look with a necklace that brings a chic detail to your everyday outfits. The necklace features a dainty layered lariat design with two flat metal bar charms. Complete your look with a basic bodysuit and high waist jeans. 

    Fit & Features

    • Dainty chain 
    • Layered design
    • Lariat charm
    • Two flat metal bars 
    • Lobster clasp

    Style Number/Barcode: 07002-0437

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty Bloom Floral Ruffle Skater Dress

    Serving soft-girl romance with a side of sass, this floral halter mini dress is made for twirls and double takes. Wear it when you want compliments on repeat.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch, floral print
    • Sleeveless V-neckline
    • Tie-back halter straps, partially open back
    • Ruching, drop waist
    • Tiered ruffled design
    • Mini-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000297

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ribbed Knit Ruched Mini Dress

    This ribbed knit ruched mini dress will be a staple in your fall wardrobe! It features a curve-hugging silhouette with ruched detailing and side tie accents. It can be worn as a cute mini or pulled down as a midi dress. Pair with some bold door knocker earrings and clear heels for that chic vibe you can wear to date night.

    Fit & Features

    • High crew neckline
    • Tank-like shoulder straps
    • Form-hugging fit
    • Ruched detailing
    • Side ties at hem
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1828

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale