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.

  • Long Mesh Duster

    This simple cover-up won't downplay your outfit! The sheer lightweight duster is perf for layering over your everyday looks. It features an open front, long fitted sleeves, and a flowy fit. The sheer mesh fabric offers a moderate stretch. Style with sleek hoop earrings.

    Fit & Features

    • Draped open front 
    • Long fitted sleeves
    • Long flowy fit 
    • Sheer mesh fabric 
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-1035

    Category Name: Vacation Looks

    Price: $14.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tied Down Flutter Sleeve Tie Front Top

    Get tied down to this cute top! Perfectly paired with denim skinnies or cut-offs, feel chic and fresh with this outfit topper! 

    Fits & Features

    • Plunging V Neckline
    • Center Tie Front 
    • Double Layer, Short Flutter Sleeves
    • Woven Lightweight Gauze Fabric 
    • Cropped Hem

     

    Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 06204-0500

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Light And Fresh Cold Shoulder Button Up Tunic

    Keep it fresh in a button up! Designed with a touch of feminine, this tunic is per for lunch out, or a celebratory party!

    Fit & Features

    • Off the shoulder fold over neckline
    • Cold shoulder design
    • Adjustable spaghetti straps
    • Long sleeves that smock at the wrist
    • Button down center | Belted waist line
    • Mini hemline | Relaxed fit
    •  Linen like material | Minimal stretch
    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.  

    Style Number/Barcode: 06003-0898

    Category Name: Vacation Looks

    Price: $16.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Waist Wide Leg Crochet Pants

    You'll be totally festival seaon ready in these trendy wide leg crochet pants!

    Fit & Features

    • High rise waist
    • Wide leg pants
    • Sheer crochet fabric
    • Minimal stretch
    • Undergarment not included

    Style Number/Barcode: 06502-0247

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sassy Strappy Back Crop Top

    Make a sassy, bold move in this strappy back crop top! Perf for the spring, pair with some high waisted denim cutoffs and sneaks!

    Fit & Features

    • Bungee spaghetti straps
    • Strappy back detail
    • Square neckline
    • Cropped
    • Stretchy knit fabric
    • Form hugging fit

    Style Number/Barcode: 06001-2633

    Category Name: Vacation Looks

    Price: $6.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fairy Tale Florals Chiffon Skater Dress

    Enchant them in this dreamy skater dress! They won't be able to keep their eyes off you 

    Fits & Features

    • Adjustable Spaghetti Straps
    • Surplice V Neckline | Back Zip With Hook & Eye Closure
    • Mini Length Hem | Flowy, Skater Style Silhouette
    • Chiffon Fabric | Floral Prints Throughout 
    • Form Hugging 

     

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

    Style Number/Barcode: 05101-0315

    Category Name: Vacation Looks

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ditsy Floral Twist Front Romper

    We love a ditsy floral print. This adorable twist front romper is calling your name! Trust us, add to cart.

    Fit & Features

    • Spaghetti straps
    • V neckline
    • Twist front detail
    • Front keyhole cut out
    • High rise banded waist | Flowy shorts
    • Ditsy floral print
    • Knit fabric | Plenty of stretch

    Style Number/Barcode: 06503-0102

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • My Vibe Floral High Waist Dress Pants

    Make floral your vibe when you slip in to this summer essential pair! Easily styled with a simple crop top, or dressed up with a sleek bodysuit!

    Fit & Features

    • High waist fit
    • Tie waist accent
    • Straight leg
    • Composed of a crepe material
    • Featuring a pop of color floral print
    • Moderate stretch
    • Form fitting down to a relaxed hemline

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

    Style Number/Barcode: 06502-0373

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Nautical Babe Striped Jumpsuit

    You'll be a total nautical babe in this spring ready striped jumpsuit! Pair with some cute wedges and you've got yourself an absolutely adorable look!

    Fit & Features

    • Off the shoulder square neckline | Ruffle trim
    • Keyhole cut out | Tie front
    • Short sleeves
    • Stretchy smocked high waist
    • Flowy wide pant legs
    • Woven fabric | Short knit lining

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 06402-0172

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • My Wavelength Skater Mini Dress

    Good vibes only in this skater dress! The mini skater dress features a deep v-neckline, spaghetti straps that offer plenty of support, back zip, a darted bust that adds structure to the bodice, a banded waist that flatters, and A-line flared skirt. Complete outfit with chic clear heels and statement earrings.

    Fit & Features

    • Sleeveless v-neckline
    • Darted seams at the bust
    • Spaghetti straps
    • Banded waist 
    • A-line skater silhouette
    • Composed of soft mid-weight woven fabric 
    • Form hugging fit

     

    Ivory and Mint Dress: Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.

    Blue Dress: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.

    Denim Dress: Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.

    Style Number/Barcode: 05101-8697

    Category Name: Vacation Looks

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Catch This Floral Romper

    Looas beautiful as a bouquet in this gorgeous romper! 

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Plunging V Neckline I Button Front Closure 
    • Lace & Zipper Detail At Back 
    • Fully Lined, Crepe Fabric 
    • Wide Leg Openings 
    • Form Hugging Fit I Moderate Stretch 

     

    Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06403-0051

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Chiffon Skater Romper

    Dress up and look enchanting in this pretty and playful romper! 

    Fits & Features

    • Adjustable Spaghetti Straps Cross At Back 
    • Surplice V Neckline 
    • Back Zipper With Hook & Eye Closure 
    • Ties At The Waist
    • Tiered Design with Shorts Underlay And Skirt Overlay 
    • Chiffon Fabric With Knit Lining 
    • Moderate Stretch

    Style Number/Barcode: 06403-0050

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunshine So Fine Hipster Swim Bottoms

    You'll look oh so fine ask you bask in the sunshine in these bold hipster swim bottoms! Don't forget to purchase the matching top!

    Shop Matching Top: Sunshine So Fine Tie Front Swim Top

    Fit & Features

    • Hipster style design
    • Cheeky bottom
    • All over contrasting hued stripes

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

    Style Number/Barcode: 07105-0600

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Delightful Charm Halter A-Line Midi Dress

    Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Woven fabric, no stretch
    • Halter pleated neckline
    • Open back, zipper and hook-eye closure
    • Beaded tie waist
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5648

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunshine So Fine Tie Front Swim Top

    You'll look oh so fine ask you bask in the sunshine in this bold tie front swim top! Don't forget to purchase the matching bottoms!

    Shop Matching Bottoms: Sunshine So Fine Hipster Swim Bottoms

    Fit & Features

    • Adjustable tank-like thin shoulder straps
    • V neckline
    • Tie front detail
    • Tie back closure
    • Removable padding
    • All over contrasting hued stripes

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

    Style Number/Barcode: 07104-0453

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Radiant And Ruffled One Shoulder Swim Top

    Look oh so radiant in this ruffle detail one shoulder swim top! Make sure to get the matching bottoms to get the perf sunkissed look bby!

    Shop Matching Bottoms: Radiant And Ruffled High Waist Swim Bottoms

    Fit & Features

    • One shoulder neckline
    • Ruffle trim
    • Removable padding

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

    Style Number/Barcode: 07104-0459

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Radiant And Ruffled High Waist Swim Bottoms

    Look oh so radiant in these ruffle detail high waist swim bottoms! Make sure to get the matching top to get the perf sunkissed look bby!

    Shop Matching Top: Radiant And Ruffled One Shoulder Swim Top

    Fit & Features

    • High rise waist
    • Ruffle hip detail
    • Cheeky bottom

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

    Style Number/Barcode: 07105-0606

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Stunner Hipster Swim Bottoms

    You'll be such a stunner as you strut down the beach in these hipster swim bottoms! Don't forget to pair them with the matching top!

    Shop Matching Top: Such A Stunner Twist Front Swim Top

    Fit & Features

    • Hispter style design
    • Side tie closures
    • Cheeky bottom

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

    Style Number/Barcode: 07105-0603

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Stunner Twist Front Swim Top

    You'll be such a stunner as you strut down the beach in this twist front swim top! Don't forget to pair it with the matching bottoms!

    Shop Matching Bottoms: Such A Stunner Hipster Swim Bottoms

    Fit & Features

    • Adjustable halter spaghetti strap | Strap is removable
    • Padded molded cups
    • Twist front detail
    • Tie back closure

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

    Style Number/Barcode: 07104-0456

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Summer Long Royal Swim Bottoms

    Add a swim suit to your collection that you can rock all summer long babe! This is it, easy to mix and match or style with its matching top, don't forget to pick it up!

    Shop Matching Top: All Summer Long Royal Mesh Swim Top

    Fit & Features

    • High rise fit
    • Mesh detail
    • Cheeky bottom
    • Moderate stretch

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

    Style Number/Barcode: 07105-0616

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Summer Long Royal Mesh Swim Top

    Add a swim suit to your collection that you can rock all summer long babe! This is it, easy to mix and match or style with its matching bottoms, don't forget to pick those up!

    Shop Matching Bottoms: All Summer Long Royal Swim Bottoms

    Fit & Features

    • Round neckline
    • Adjustable spaghetti straps
    • Mesh detailing above the hemline
    • Not-padded
    • Moderate stretch

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

    Style Number/Barcode: 07104-0469

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Waist Belted Denim Shorts

    Stylishly cinch your look with these trendy high waist belted denim shorts! Pair with a graphic tee and some booties to add some effortless edge.

    Fit & Features

    • High rise waist
    • Included denim belt
    • Front buttons | Hidden zipper closure
    • Slanted front pockets | Back pockets
    • Fitted shorts
    • Denim fabric | No stretch

    Style Number/Barcode: 06603-0099

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Floral Bell Sleeve Top

    Look just as sweet as can be in this adorable floral bell sleeve top! Pair with some high rise white denim cut off shorts or jeans and strappy heels for the perf fresh spring time vibe.

    Fit & Features

    • Long bell sleeves
    • V neckline
    • Tie front detail
    • Cropped
    • All over floral print
    • Polyester woven fabric

    Style Number/Barcode: 06204-0560

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fab Day Tassel Fan Earrings

    Make your day a fab one with these fun tassel earrings to give your outfit a pop of color. 

    • Hammered Metal on Post
    • Fish Hook Back
    • Mint Colored 
    • Long Fan Tassel 

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

    Style Number/Barcode: 07001-0574

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale