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.

  • Adorable Looks Tie Front Bodycon Midi Dress

    All of your adorable looks this season will include this eyelet midi dress with a flirty tie front and bodycon silhouette. This dress is perfect for shower celebrations or graduations!

    Fit & Features

    • Eyelet fabric
    • Tie front sweetheart neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6008

    Category Name: Vacation Looks

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Main Stage Energy Fringe Denim Shorts

    Built for the spotlight and made to move—these denim shorts bring big fringe energy. The high-rise waist snatches your silhouette while the side fringe brings the drama.

    Fit & Features

    • Denim fabric
    • High-rise waist
    • Five-pocket and belt loop design
    • Front button closure
    • Side fringe detailing
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-000064

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Flair Floral Lace-Up Maxi Dress

    Bring the romantic flair in this gorgeous floral print maxi dress with a form-hugging silhouette to highlight your curves. The alluring open lace-up back will turn heads and capture all the attention.

    Fit & Features

    • Knit fabric, high stretch
    • Floral print
    • Sleeveless V-neckline
    • Open back, cross-back lace-up design
    • Maxi-length hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000055

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Statement Paisley Boho Satin Scarf

    Create a statement look with this paisley boho satin scarf with versatile styling options! Wrap it around your head, tie it around a bag or your waist for a trendy and sassy vibe.

    Fit & Features

    • Paisley boho print
    • Smooth silky satin material

    Style Number/Barcode: 07305-000001

    Category Name: Vacation Looks

    Price: $3.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bohemian Vibes Crochet Knit Maxi Skirt

    This crochet knit maxi skirt will bring those boho vibes to your trendy festival 'fit! Designed with a high-cut side slit, style with the matching crop top for an alluring look.

    Shop Matching Top: Bohemian Vibes Crochet Knit Crop Top

    Fit & Features

    • Sheer crochet knit fabric
    • High-rise waist, tie-front detail
    • High side slit
    • Maxi-length hem
    • Fitted silhouette
    • Runs true to size
    • Undergarments not included

    Style Number/Barcode: 06501-1137

    Category Name: Vacation Looks

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Into The Sun V-Neck Maxi Dress

    Sun goddess maxi dress boasting a V-neckline with a unique metal accent and a body-skimming silhouette. Style with strappy sandals for a sunset dinner.

    Fit & Features

    • Textured knit fabric, soft knit stretchy lining
    • V-neckline with metal accent
    • Spaghetti straps
    • Body-skimming silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000002

    Category Name: Vacation Looks

    Price: $45.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: L

  • Going On Vacation Straw Clutch Bag

    Keep your vacation essentials in this cute straw clutch bag with a detachable chain strap for versatile styling!

    Fit & Features

    • Top handles
    • Pull apart closer
    • Detachable chain strap
    • Spacious lined interior with pocket

    Style Number/Barcode: 07203-000008

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fave Chic Cutout Strap Sandals

    Your new fave chic sandals have arrived for everyday wear. Featuring an open square toe and a cutout strap design, you'll love styling these with your casual 'fits.

    Fit & Features

    • Faux leather material
    • Open square-shaped toe
    • Cutout strap design
    • Open back, on-and-off styling
    • Flat sole
    • Runs true to size

    Style Number/Barcode: 07404-1263

    Category Name: Vacation Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Fave Linen Slingback Stiletto Pumps

    These slingback stiletto pumps will be your new summer fave, designed with circular buckle accents and chic linen material.

    Fit & Features

    • Stiletto heel
    • Linen material
    • Closed pointed toe
    • Circular buckle accents
    • Slingback adjustable strap
    • Cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-000077

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Beauty V-Neck Slit Midi Dress

    Jet set on your next tropical getaway or weekend escape in this perfect slit midi dress! Featuring a bold metal insert and a flattering bodycon fit, this dress is perfect for any occasion. 

    Fit & Features

    • Palm leaf tropical print, stretchy knit fabric, soft knit lining
    • V-neckline with metal insert
    • Spaghetti straps
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6095

    Category Name: Vacation Looks

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Beauty In The Tropics Flower Strappy Mules

    Take your vacation look up a notch in these tropical flower mules with a strappy design and stiletto heel.

    Fit & Features

    • 2.5" Stiletto heel
    • Square toe
    • Tropical flower, strappy design
    • Patent leather material
    • Runs true to size

    Style Number/Barcode: 07401-000218

    Category Name: Vacation Looks

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Beauty Strappy Back Floral Maxi Dress

    Aim to charm effortlessly in this floral maxi dress while on vacation for a sunset dinner! With its stunning strappy back and curve-hugging fit, this dress is a must to pack.

    Fit & Features

    • Floral print, mesh fabric, stretchy knit lining
    • Square neckline, padded bra cups
    • Spaghetti straps
    • Strappy back, lower zipper and hook-eye closure
    • Curve-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000829

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: WHITE, BLUE

    Available Size: XS, S, M, L

  • Sunny Day Plans Bow Espadrille Wedges

    Your sunny day plans aren't complete without these espadrille wedges! These stylish shoes feature a crisscross toe strap adorned with an adorable bow, while the wedge sole elevates your outfit.

    Fit & Features

    • Wedge heel
    • Square toe
    • Crisscross toe strap with bow
    • Espadrille sole
    • Adjustable ankle strap, buckle closure
    • Runs true to size

    Style Number/Barcode: 07406-000010

    Category Name: Vacation Looks

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Beaded Straw Cowboy Hat

    Capture a chic western look with this beaded straw cowboy hat to top off your concert or festival outfit!

    Fit & Features

    • Beaded string 
    • Curved wide brim
    • Adjustable interior strings for a snug fit
    • Straw material

    Style Number/Barcode: 07302-000003

    Category Name: Vacation Looks

    Price: $3.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Key Oversized Chain Sunglasses

    Make a statement that's anything but subtle in these oversized square sunglasses! Designed with edgy chain arms and cool tinted lenses that give your look an effortlessly trendy touch.

    Fit & Features

    • Oversized square frames
    • Tinted lenses
    • 100% UV protection
    • Chain arms
    • Rubber nose supports

    Style Number/Barcode: 07008-1138

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Super Star Mid-Rise Denim Shorts

    Creating trendy looks is easy with these mid-rise denim shorts with a head-turning star back design and a cut-off hem for a touch of edge!

    Fit & Features

    • Light wash denim fabric
    • Mid-rise waist
    • Star back design
    • Front seam details
    • Cut-off hem
    • Runs true to size

    Style Number/Barcode: 06603-000027

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Livin' My Best Life Oversized Square Sunglasses

    These oversized sunglasses are sure to become an instant favorite! Perfect for any occasion, slip into these cool shades with edgy metal trim sides.

    Fit & Features

    • Oversized square frames
    • Metal trim sides
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1137

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Style Tropical Halter Mesh Maxi Dress

    Get that tropical feeling whenever you wear this halter mesh maxi dress! The cowl neckline adds a touch of elegance while the form-hugging fit flatters your curves, perfect for vacations or beach days.

    Fit & Features

    • Tropical print, mesh-lined fabric
    • Cowl halter neckline
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4081

    Category Name: Vacation Looks

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Days Off Scoop Neck Smocked Skater Dress

    Grab your favorite sunnies cause it's time to take a sunny stroll in this skater dress down by the beach or to the coffee shop! With adjustable straps and a stretchy smocked bust, this dress provides the perfect fit every time. The playful ruffled skater silhouette and short-length hem make it a must-have for any sunny day. Complete the look with strappy sandals.

    Fit & Features

    • Airy woven fabric with woven lining
    • Adjustable spaghetti straps
    • Scoop neckline
    • Stretchy smocked bust
    • Ruffled skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5462

    Category Name: Vacation Looks

    Price: $39.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • American Honey Baseball Cap

    It's the land of the free and the home of babes like you in this baseball cap featuring "American Honey" embroidered across the front to flaunt your status.

    Fit & Features

    • Two-tone design
    • Embroidered "American Honey"
    • Adjustable back strap
    • Curved wide brim

    Style Number/Barcode: 07302-000002

    Category Name: Vacation Looks

    Price: $7.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Coastal Chic Starfish Charm Necklace

    This stunning necklace features a faux pearl starfish charm that adds a chic touch while connecting you to the beauty of the ocean!

    Fit & Features

    • Faux pearl trim starfish charm
    • Dainty chain
    • Lobster clasp closure

    Style Number/Barcode: 07002-000056

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mermaid Core Starfish Stud Earrings

    Play up your summer looks with these trendy starfish stud earrings that give off a mermaid core vibe.

    Fit & Features

    • Large starfish design
    • Post-back closure

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-000052

    Category Name: Vacation Looks

    Price: $2.97 $7.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Serving Summer Raffia Stretch Belt

    You'll be serving all the summer vibes in this raffia woven textured belt with a stretch design and front curved metal buckle.

    Fit & Features

    • Raffia woven material
    • Stretch design
    • Front curved metal buckle closure

    Style Number/Barcode: 07301-000008

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sandy Shores Tropical Floral Maxi Skirt

    This vibrant tropical floral maxi skirt will transport you to the sandy shores of a tropical paradise. With its stunning print and flattering high-rise waist, this skirt is perfect for any summer occasion. Pair with the matching top.

    Fit & Features

    • Tropical floral print, stretchy knit fabric
    • Strapless neckline
    • Fitted crop hem
    • Runs true to size

     

    Shop the Matching Top: Sandy Shores Tropical Floral Crop Top

    Style Number/Barcode: 06501-000049

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale