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.

  • Zip Front Crossbody Satchel

    This zip front crossbody satchel is the perfect accessory for all your looks! It features a rectangular design with zippered pockets on both sides, a zippered top with multiple pockets on the lined interior, and an adjustable detachable shoulder strap. Bag is composed of a black faux leather material.

    Style Number/Barcode: 07203-1910

    Category Name: Vacation Looks

    Price: $14.45 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Locked In Chevron Backpack

    Keep all your essentials secure and stylish in this trendsetting back pack! It features a solid black hue, a top handle, top zipper closure with gold metal hardware, a front pocket with a snap button closure, a gold chain-link detail, adjustable shoulder straps and a quilted chevron design. Backpack is composed of a faux leather material and includes a lined interior. 

    Style Number/Barcode: 07203-1925

    Category Name: Vacation Looks

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In The Dome Crossbody Bag

    Zone in on complementing that 'fit with this chic black bag! It features a dome design with a top zipper opening, two side openings, metallic gold hardware, and an adjustable and detachable shoulder strap. Crossbody bag is composed of a faux leather material. 

    Style Number/Barcode: 07203-1880

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Elevated Elegance Envelope Clutch

    Add a touch of elegance to your look with a statement clutch! This must have features an envelope design, a fold over closure with insert, a large zippered pocket, a small interior pocket and a dainty chain shoulder strap. Clutch is composed of a faux leather material.

    Style Number/Barcode: 07203-1876

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Clear As Day Back Pack

    This backpack is clear as day! Literally. It has a two zipper compartment paired with adjustable straps and a basic handle at the top. The clear bag is composed of a pvc material with a black trim and gold metal details. It's the perfect piece for that upcoming festival!

    Style Number/Barcode: 07203-1903

    Category Name: Vacation Looks

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mini Buckle Detail Saddle Bag

    This mini saddle bag will stylishly complete your look and hold all of your essentials! It features a fold-over design with a magnetic closure and a gold buckle detail, a front pouch, and a detachable faux leather and gold chain shoulder strap. The bag is composed of a gray faux leather material.

    Style Number/Barcode: 07203-1895

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Slay In Snake Mini Backpack

    Slay your look with trendsetting snake! Keep your essentials close to you with this mini backpack that features a top zipper closure with a large removable black pom pom accent, two side pockets, a front zippered pocket, a faux leather black hued trim, a top handle strap and adjustable faux leather shoulder straps. The all over snake print features taupe and gray hues for that minimal vibe! 

    Style Number/Barcode: 07203-1898

    Category Name: Vacation Looks

    Price: $16.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • One Sided Sleeveless Cutout Bodysuit

    Show off your good side in this sleeveless bodysuit for any casual plans! Featuring a cutout one-shoulder neckline, this form-hugging bodysuit is designed to accentuate your curves. The thong bottom with snap button closures adds a secure fit. Complete the look in denim shorts for a day out.

    Fit & Features

    • Double-lined brushed knit stretchy fabric
    • Cutout one-shoulder neckline
    • Form-hugging fit
    • Thong bottom, snap-button closures
    • Runs true to size

    Style Number/Barcode: 06001-5239

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Belted Fanny Pack

    Keep your festival 'fit on point while still having the essentials with this faux leather fanny pack! It features a black belt with a silver buckle that attaches to a large pouch with a fold over button closure. The pouch has slots on the back to attach an included thigh belt strap for a trendy look!

    Style Number/Barcode: 07203-1854

    Category Name: Vacation Looks

    Price: $9.45 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Network Skills Backpack

    Expand your network with this conversation starter! The black backpack has a large compartment paired with an outer compartment that features two zipper pockets and is composed of a double sided fishnet material.

    Style Number/Barcode: 07203-1848

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Electric Neon Fanny Pack

    Add an electric pop of color to your outfit with this neon pink fanny pack! It features a top zipper opening, faux leather details, and an adjustable waist strap with a buckle closure. Fanny pack is composed of a nylon material. 

    Style Number/Barcode: 07203-1875

    Category Name: Vacation Looks

    Price: $7.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Boho Vibe Straw Cross Body

    Channel those boho vibes just in time for festival with this trendy cross body! It features a multi colored body, an envelope design with fold over snap closure and a lined interior with small zippered pocket. The tribal-inspired print features natural, black and tan hues for an eathy vibe! Includes a detachable gold chain strap. Composed of a straw-like material.

    Style Number/Barcode: 07203-1874

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Faux Leather Quilted Chevron Backpack

    Keep all your essentials secure and stylish in this versatile back pack! It features a solid black hue, a top handle, top zipper closure with gold metal hardware, side pockets, adjustable shoulder straps and a quilted chevron design. Backpack is composed of a faux leather material and includes a lined interior. 

    Style Number/Barcode: 07203-1873

    Category Name: Vacation Looks

    Price: $21.00 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hello Weekend Straw Tote Bag

    Get all of those end of the week feels with this super cute tote bag! It features top handles, a front button closure, and a front velcro closure pouch with the script, "Hello Weekend." The bag is made of a woven straw-like material and is perfect for all of your upcoming summer outings!

    Style Number/Barcode: 07203-1844

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Quilted Crossbody Fanny Pack Belt

    This trendy quilted bag will step up your accessory game for sure! It features a square shaped fold-over design with a silver turn lock closure with a black and white hued lined divided interior with card slots, a zippered pocket, and an included garment bag. The exterior is composed of a pink quilted faux leather material with loops with a belt to covert it to a fanny pack as well as links inside with a silver chain to convert it to a crossbody. 

    Style Number/Barcode: 07203-1858

    Category Name: Vacation Looks

    Price: $11.45 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fiercely On Trend Wristlet

    This black hued wristlet is fiercely on trend! It features a rectangular shape with a fold over design with a gold metal trim accent and snap button closures. The interior has card slots and a zippered pouch. Includes a gold chain with a faux leather shoulder strap to convert the bag to a crossbody and a faux leather wristlet. The exterior has an open pouch and is composed of a faux leather material.

    Style Number/Barcode: 07203-1796

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tassel Straw Clutch

    Fun and flirty! This dome shaped clutch has a straw exterior and multi-colored tassel details with a zipper closure.

    Style Number/Barcode: 07203-0046

    Category Name: Vacation Looks

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Straw Striped Clutch

    Your next fave casual clutch is here! It features a straw weave with a multi colored striped pattern, an envelope design, and a large tassel accent. Detachable gold chain included.

    Style Number/Barcode: 07203-0059

    Category Name: Vacation Looks

    Price: $11.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Stripes Swimsuit
    Sun and stripes is all you need for the perfect summertime look! This swimsuit features a plunging V neck, narrow criss crossing straps, a midriff cut out and a cheeky bottom. The back features an open back with narrow tie accents. The all over narrow stripe pattern features black and white hues for a classically chic look! 

    RETURNS ACCEPTED ONLY WHEN ALL TAGS AND HYGIENIC PROTECTION ARE INTACT.

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

    Style Number/Barcode: 07109-0111

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Essential Chevron Cross Body

    Take everything you need in this cute cross body! It features a vibrant red color, a chevron design, a top open gold zipper closure with tassel accent, large exterior pocket and a detachable gold chain shoulder strap.  

    Style Number/Barcode: 07203-0024

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Clearly Chic Handbag

    Clearly stay on trend with this cute bag to keep all your favs close to you! The purse has a flap front with a clasp closure and includes a chain strap. The handbag is composed of a pvc material and features a rose gold trim paired with gold, metal accents.

    Style Number/Barcode: 07203-0013

    Category Name: Vacation Looks

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strut And Snap Ribbed Knit Midi Dress

    Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Ribbed knit fabric with moderate stretch
    • Square neckline
    • Tank shoulder straps
    • Metal button accents
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-1167

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beachin' It Netted Tote

    This boho chic netted tote is totes perfect for beachin' it! It features a curved wooden handle and a black hued netted pouch.

    Style Number/Barcode: 07203-0021

    Category Name: Vacation Looks

    Price: $13.45 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Cutie Mini Backpack
    Carry all your essentials in this must have! The black mini backpack features a top zipper closure, a front zippered pocket, removable adjustable straps and a top handle. The body is composed of faux croc embossed material.

    Style Number/Barcode: 07203-0009

    Category Name: Vacation Looks

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free