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.

  • Peep This Chrome Iridescent Rhinestone Sandals

    Peep that pedi girl! The shine is real with these slides, show off those toes in the realist way. Style perfectly with cut off denim and a cropped top, or with your swimsuit on the beach!

    • Open almond toe
    • Double row rhinestone trim
    • Thick clear band over the toe 
    • Rhinestone embellishments 
    • Chrome lining
    • Iridescent finish

    Style Number/Barcode: 07404-0140

    Category Name: Vacation Looks

    Price: $12.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Walk In The Park Tiered Romper

    Show up to your daytime date in this flowy and chic dress! Pair your look with a lovely rattan cross-body bag and some heels to match!

    Fits & Features

    • Spaghetti Straps
    • Scoop Neckline
    • Tie Back I Cut Out Opening 
    • Wide Leg Shorts I Tiered Skirt Overlay 
    • Woven Fabric 
    • Form Hugging Fit 

    Style Number/Barcode: 06403-0114

    Category Name: Vacation Looks

    Price: $13.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Peep The Pedi Square Toe Croc Sandals

    Peep the pedi and then watch me stride away in my cute af square toe sandals~

    • Slide on fit 
    • Square toe
    • Flat sole
    • Faux leather
    • Embossed with crocodile print

    Style Number/Barcode: 07404-0563

    Category Name: Vacation Looks

    Price: $11.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Totally Boho Smocked Waist Jumpsuit

    Get a total boho babe look in this relaxed fitting casual cute jumpsuit! Pair with some strappy sandals and a floppy hat to complete your vibe.

    Fit & Features

    • Short billowy sleeves | Beaded drawstrings to cinch
    • V neck and back
    • Stretchy smocked waist
    • Hidden pockets
    • Loose fitting pant legs | Smocked cuffs
    • Lightweight woven fabric
    • Overall relaxed, comfortable fit

    Style Number/Barcode: 06302-0143

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Blossum Babe Mesh Duster

    Babe, you'll blossum with beauty in this lightweight airy mesh duster! The all over floral print will pair perf with a simple top and some light wash jeans.

    Fit & Features

    • Long fitted sleeves
    • Open front
    • Sheer mesh fabric | Plenty of stretch
    • All over floral print
    • Flowy, relaxed fit

    Style Number/Barcode: 06202-0084

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Match Chevron Knit Midi Skirt

    Trend right with this chevron knit midi skirt for weekend fun or vacation! Pair with the matching top to complete the look.

    Fit & Features

    • Chevron pattern, stretchy knit fabric
    • High-rise waist
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Shop The Matching Top: Trendy Match Chevron Knit Tube Top

    Style Number/Barcode: 06501-1136

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S

    Product Badge:
    • Sale
  • On Vacay Tropical Mesh Duster

    She's out of office and on vacay! Pair this tropical duster with your fave bikini set and head straight to the beach! Don't forget to pick up a mojito on your way there 

    Fits & Features

    • Long Fitted Sleeves 
    • Open Front Design 
    • Belt Loops & Drawstring Waist 
    • Duster Length 
    • Sheer Unlined Mesh Fabric With Tropical-Inspired Prints
    • Relaxed Fit 

    Style Number/Barcode: 06202-0069

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Kimono Sleeve Tie Front Top

    Add some floral flair to your everyday look by layering on this pretty kimono sleeve tie front top! Dress it down with some jeans and sandals for a perf spring time feel.

    Fit & Features

    • Three quarter length kimono sleeves
    • V neckline
    • Tie front
    • Cropped
    • Floral print
    • Wool dobby woven fabric
    • No stretch

    Style Number/Barcode: 06204-0422

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vitamin Sea Lace-Up Front Swim Tank

    It's essential. You're going to need a cute swimsuit for all those beach and poolside visits! Just make sure you add the matching bottoms to cart! 

    Shop Matching Bottoms: Vitamin Sea Hipster Swim Bottoms 

    Fits & Features

    • Off Shoulder Straps
    • Adjustable Lace-Up Front Design 
    • Removable Padded Bust 
    • Fully Lined Moderate Stretch
    • Swim Bottoms Sold Separately 

     

    Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small

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

    Style Number/Barcode: 07104-0440

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vitamin Sea Hipster Swim Bottoms

    It's essential. You're going to need a cute swimsuit for all those beach and poolside visits! Just make sure you add the matching top to cart! 

    Shop Matching Bottoms: Vitamin Sea Lace-Up Front Swim Tank

    Fits & Features

    • Mid-Rise Waist
    • Mesh Lined
    • Hipster Fit
    • Moderate Stretch
    • Matching Swim Top Sold Separately 

     

    Model is 5'7" with a 32" bust, 24" waist and 37" hips. She is wearing a size small

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

    Style Number/Barcode: 07105-0588

    Category Name: Vacation Looks

    Price: $9.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In The Clear Molded Transparent Bra
    Clearly stay on trend with this head turning bra! Style with rhinestones and sequins and everything flashy!
    Fit & Features
    • Molded cups
    • Adjustable clear straps
    • Fasten closure
    • Completely sheer | Pasties not included
    • White underwire lining
    • Latex free

     

    For sizing, Small is equivalent to an A, Medium to a B and Large to a C. 

    Style Number/Barcode: 07107-0403

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Isadora Lace Two Piece Chiffon Floral Dress

    Special Occasion

    Glide through the room and ooze an ethereal presence in our charming Isadora! With a heavenly lace top and a dreamy floral chiffon skirt to match, these complementary pieces are the perfect fit. Our Isadora will have you standing out against the crowd in an enchanting fashion. 

    Fits & Features

    • Off Shoulder Scalloped Neckline & Sheer Short Sleeves
    • Lace Crafted Crop Top 
    • Fully Lined, Chiffon Skirt I Pleating Throughout
    • Floor Length Hemline I Wrap Skirt With Slit
    • Back Zipper With Hook & Eye Closure 
    • Moderate Stretch 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05006-0326

    Category Name: Vacation Looks

    Price: $42.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Love Chiffon Ruffle Strap Maxi Dress

    Romance is in the air! Take everyone's breath away with this charming maxi dress! 

    Fits & Features

    • Ruffle-Trim Shoulder Straps 
    • Surplice V Neckline I Smocked Back 
    • Adjustable Waist Tie
    • Maxi Length Silhouette I Partial, Mini Length Knit Lining
    • Wrap Skirt Reveals Front Slit 
    • Chiffon Fabric 
    • Moderate Stretch 

    Style Number/Barcode: 05101-0781

    Category Name: Vacation Looks

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Flirt Ruffle Hem Mini Dress

    You'll be a major flirt in this absolutely adorable ruffle hem mini! The dress is perf paired with some wedges for a spring day out!

    Fit & Features

    • Short sleeves
    • Wrap front | V neckline
    • High rise elastic banded waist
    • Wrap front skirt | Ruched detailing
    • Ruffle hem
    • Stretchy knit fabric

    Style Number/Barcode: 05102-0651

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Center Of Attention Ruched Mini Dress

    Be the center of attention in this sultry mini dress! Pair with some booties or heels for a chic look! 

    Fits & Features

    • V Neckline 
    • Roomy Sheer Long Sleeves 
    • Elastic Shoulder & Cuffs 
    • Adjustable Drawstring Center Front 
    • Mini Length Silhouette 
    • Mesh Lined Fabric 
    • Form Hugging Fit I Moderate Stretch 

    Style Number/Barcode: 05102-0696

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Livin' It Up Ruched Mini Dress

    You're out here livin' your best life, and babe we're here for it! Pair this sexy ruched mini dress with some strappy heels for a fun night out.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Ruched sides with drawstrings at hem
    • Short, curve hugging fit
    • Stretchy knit fabric

    Style Number/Barcode: 05102-0612

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect Pick Floral Swim Bottoms

    These pretty and vibrant floral swim bottoms will be the perfect pick for your spring break getaway! Be sure to get the matching top for an all together stunning look.

    Shop Matching Top: Perfect Pick Floral Swim Top

    Fit & Features

    • High rise waist
    • Ruched side detailing
    • Cheeky bottom
    • All over floral print

    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07105-0497

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Babe Halter Swimsuit

    You'll be a major babe in this floral halter one piece swimsuit! Perf for your spring break getaway, pair with some oversized sunnies and get ready to relax bb!

    Fit & Features

    • Halter neck | Tie closure
    • Deep plunging V neckline
    • Removable padding
    • Low scoop back
    • High waist
    • Cheeky bottom
    • All over floral print

    Model is 5'8" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

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

    Style Number/Barcode: 07109-0206

    Category Name: Vacation Looks

    Price: $14.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Pick Floral Swim Top

    This pretty and vibrant floral swim tank will be the perfect pick for your spring break getaway! Be sure to get the matching bottoms for an all together stunning look.

    Shop Matching Bottoms: Perfect Pick Floral Swim Bottoms

    Fit & Features

    • Thin shoulder straps
    • Deep V neckline
    • Faux tie front detail
    • Hook and bar back closure
    • All over floral print
    • Removable padding

    Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.

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

    Style Number/Barcode: 07104-0346

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Eyes on You Lace Low Back Midi Dress

    Soft girl era, but make it spicy. With a sheer midi hem, sultry low back, and flirty side slit, this is the “accidentally iconic” dress for nights out, beach dates, or brunches.

    Fit & Features

    • Stretch lace knit fabric, partially lined
    • V-neckline, spaghetti straps
    • Low back cut
    • Curve-hugging silhouette
    • Sheer midi hem, side slit
    • Runs true to size

    Style Number/Barcode: 05102-000222

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Ready Rose Print Swim Bottoms

    Get totally vacay ready in these too cute rose print swim bottoms! Paired with the matching top, you'll be lookin' absolutely adorable.

    Shop Matching Top: Vacay Ready Rose Print Swim Top

    Fit & Features

    • Top ruffle trim
    • Side tie closures
    • Cheeky bottom
    • All over small rose print

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

    Style Number/Barcode: 07105-0498

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea Me Now Tie Side Hipster Swim Bottoms

    Wait till they see you! Turn heads in this flirty and fun swimsuit. Make sure you add the matching top to cart to complete the look! 

    Shop Matching Top: Sea Me Now Ruffle Trim Molded Swim Top

    Fits & Features

    • Mid-Rise Waist
    • Tie Sides
    • Cheeky Fit
    • Fully Lined 
    • Matching Top Sold Separately 

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

    Style Number/Barcode: 07105-0579

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreaming of Summer Ombre Swim Bottoms

    We're dreaming of sunny days and poolside vibes in these ombre swim bottoms! Don't forget to pair these must haves with the matching top! 

    Shop Matching Swim Top: Dreaming of Summer Ombre Swim Top

    Fit & Features

    • Hipster Rise Waist 
    • Cheeky Bottom 
    • Tie-Dye Ombre Pattern

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

    Style Number/Barcode: 07105-0595

    Category Name: Vacation Looks

    Price: $8.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Ready Rose Print Swim Top

    Get totally vacay ready in this too cute rose print swim top! Paired with the matching bottoms, you'll be lookin' absolutely adorable.

    Shop Matching Bottoms: Vacay Ready Rose Print Swim Bottoms

    Fit & Features

    • Thin ruffle shoulder straps
    • Sweetheart neckline
    • Wired bust | Light padding
    • Small front cut out | Tie front detail
    • Back hook and bar closure
    • All over small rose print

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

    Style Number/Barcode: 07104-0347

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free