Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

Get Eye-Catching Sandals For Women

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.

  • Trendy Adventure Strapless Paisley Satin Crop Top

    Endless summer adventures call for this trendy paisley satin crop top! Featuring a flattering strapless neckline, a stretchy smocked bandeau lining, and a tie-back closure for the perfect fit. Complete the look in denim shorts and sunglasses!

    Fit & Features

    • Paisley print, non-stretch satin fabric
    • Strapless neckline
    • Tie back design
    • Stretchy smocked bandeau lining
    • Pointed crop hem
    • Runs true to size

    Style Number/Barcode: 06003-2544

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Catch Tie Front Knit Bandeau

    Catch this stylish bandeau top for the ultimate vacation look! Featuring a strapless sweetheart neckline and a tie-front bust for a flirty allure while the ultra-cropped hem adds a trendy touch. Complete the look with the matching skirt.

    Shop Matching Bottoms: Stylish Catch High Rise Slit Midi Skirt

    Fit & Features

    • Knit fabric, sewn-in knit lining, minimal stretch
    • Strapless sweetheart neckline
    • Tie-front bust
    • Ultra-cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2418

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Social Butterfly Flower Hoop Earrings Set

    The perfect three-pack earring set to adorn all of your outfits for everything on the calendar! This set has one pair of rhinestone embellished butterflies, one pair of flowers, and one pair of rhinestone trim hoop earrings each with post-back closures. Complete the look with dressy heels.

    Fit & Features

    • Thre-pack earrings set
    • One pair of rhinestone butterflies
    • One paid of flowers
    • One pair of rhinestone trim hoop earrings
    • Post-back closures

     

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

    Style Number/Barcode: 07001-2032

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bloom With A View Floral Tube Top

    Wherever your travels take you, this floral tube top is here to make your view that much prettier! Designed to flatter, this top has a sleek strapless neckline and fitted crop hem that highlights your figure. Pair with the matching skirt to complete the look.

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining, moderate stretch
    • Strapless tube neckline
    • Fitted crop hem
    • Runs true to size

     

    Shop The Matching Skirt: Bloom With A View Floral Mini Skirt

    Style Number/Barcode: 06001-000140

    Category Name: Vacation Looks

    Price: $24.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Loving Heart Shell Necklace

    Fall for this heart shell necklace to adorn your vacation or weekend outfit! Complete the look in cute sandals.

    Fit & Features

    • Heart shell charm
    • Cord strand
    • Lobster clasp closure

    Style Number/Barcode: 07002-1838

    Category Name: Vacation Looks

    Price: $2.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bloom With A View Floral Mini Skirt

    Wherever your travels take you, this floral mini skirt is here to make your view that much prettier! Designed to flatter, this skirt has a sleek mid-rise waist and bodycon silhouette that highlights your figure. Pair with the matching top to complete the look.

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining, moderate stretch
    • Mid-rise waist
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

     

    Shop The Matching Top: Bloom With A View Floral Tube Top

    Style Number/Barcode: 06501-000048

    Category Name: Vacation Looks

    Price: $26.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Part of a Set
  • Keep It Chic Doorknocker Hoop Earrings

    Keep your everyday 'fits chic and on-trend with these sleek doorknocker hoop earrings! They feature a large teardrop-shaped post with a hanging hoop design. Include a post-back closure. Complete the look with a ring set.

    Fit & Features

    • Large teardrop post
    • Hanging hoop design
    • Post-back closure

     

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

    Style Number/Barcode: 07001-1986

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She’s The Moment Tie-Front Halter Top

    Serving main character energy with every knot—this top is that girl. The halter V-neck and flirty tie-fronts give it an effortlessly hot vibe that’s perf for your next weekend adventure.

    Fit & Features

    • Twill woven fabric
    • Sleeveless halter V-neckline
    • Multi-tie-front design
    • Partially open back
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-000068

    Category Name: Vacation Looks

    Price: $36.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L

  • Season Staple Denim Print Faux Leather Shoulder Bag

    Trendy with a chic structure, this denim print faux leather shoulder bag is a staple for the season. Designed with a medium-wash denim print on smooth faux leather material, this bag is a fabulous must-have! It features a small half-moon shape with curved seam accents, a snap button closure with a buckle strap accent, a top zipper closure to secure your essentials in the spacious woven interior, and an adjustable shoulder strap. Pair with the matching heels for a seamlessly stylish 'fit!

    Shop Matching Heels: Season Staple Denim Print Faux Leather Stiletto Heels

    Fit & Features

    • Faux leather material with medium-wash denim print
    • Small half-moon design
    • Snap button closure with buckle strap accent
    • Top zipper closure
    • Woven interior with pouch and zippered pocket
    • Adjustable shoulder strap
    • Black is solid faux leather material

    Style Number/Barcode: 07203-2018

    Category Name: Vacation Looks

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Looks V-Neck Lace Babydoll Dress

    Sweeten any occasion in this lace babydoll dress with a charming ruffled silhouette and mini-length hem!

    Fit & Features

    • Lace fabric, stretchy knit lining
    • V-neckline
    • Adjustable spaghetti straps
    • Ruffled babydoll silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000093

    Category Name: Vacation Looks

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: M, L

    Product Badge:
    • Best Seller
  • Whimsical Chic Organza Butterfly Statement Earrings

    Create an enchanting spring or summer party look with these whimsical butterfly statement earrings! They feature a gorgeous long cascading design with a dainty chain, large and small sheer organza butterfly accents, and a sparkling round rhinestone detail at the end. Include a fish hook closure. Style with a ring set.

    Fit & Features

    • Long linear design
    • Dainty chain
    • Sheer organza butterfly accents
    • Round rhinestone detail
    • Fish hook closure, rubber stopper


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

    Style Number/Barcode: 07001-1991

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fun In The Sun Raffia Platform Block Heels

    Have fun in the sun in these cute raffia heels designed to elevate your look with a platform sole, block heel, and a cushioned insole that keeps you comfortable all day! 

    Fit & Features

    • 4.5" Block heel
    • Almond toe, crisscross toe straps
    • Adjustable ankle strap, buckle closure
    • Platform sole
    • Luxe fit cushioned insole
    • Raffia material
    • Runs true to size

    Style Number/Barcode: 07401-5331

    Category Name: Vacation Looks

    Price: $34.90

    Availability: In Stock

    Available Color: NUDE

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

    Product Badge:
    • Best Seller
  • Here Comes The Sun Strapless Ruffled Mini Dress

    Here comes the sun and you radiating trendy vibes in this strapless mini dress perf for casual plans! The ruched sides and ruffled hem add a playful touch to the bodycon silhouette.

    Fit & Features

    • Double-lined brushed knit fabric, moderate stretch
    • Strapless straight neckline
    • Ruched side seams
    • Bodycon silhouette
    • Mini-length tiered ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5922

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: YELLOW, BROWN

    Available Size: M, L, XS, S

  • Chic Flair Oversized Square Sunglasses

    Add that chic flair to your everyday looks with these sleek square sunglasses! They feature an oversized square-shaped design, a trendy tortoiseshell plastic frame and arms, built-in nose pads for support, and tinted lenses. Style these shades with a faux leather handbag.

    Fit & Features

    • Oversized square-shaped design
    • Tortoiseshell plastic frame and arms
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1072

    Category Name: Vacation Looks

    Price: $4.97 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fab Trendsetter Rectangle Sunglasses

    Top off your fab summer 'fits with these trendy shades! The sunglasses feature a rectangular-shaped design, a plastic frame with a glam metallic sheen, built-in nose pads, and tinted lenses. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Rectangular-shaped design
    • Plastic frame, metallic sheen
    • Built-in nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-1090

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Perfect Day Puff Espadrille Wedge Sandals

    From beach vacations to sunset cocktails, these wedge sandals are perfect for summer fun! Featuring a square toe and a unique woven puff strap, you'll stand out in style. The espadrille platform wedge sole and padded faux leather footbed add comfort and elevated trendiness. Complete the look with a chic purse.

    Fit & Features

    • 2" Wedge heel
    • Square toe
    • Woven puff strap
    • Espadrille platform sole
    • Padded faux leather footbed
    • Runs true to size

    Style Number/Barcode: 07406-0358

    Category Name: Vacation Looks

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Best Times Doorknocker Earrings

    The best times start with the best accessories like these earrings! They feature a statement doorknocker design and a post-back closure. Complete the look in a bodycon dress for date night.

    Fit & Features

    • Dooknocker design
    • Post back closure

     

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

    Style Number/Barcode: 07001-2031

    Category Name: Vacation Looks

    Price: $7.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Structure Cuff Bracelet

    You'll obsess over the sleek structure of this trendy cuff bracelet! It features a teardrop-shaped overlapping design with a snap closure. Style with hoop earrings.

    Fit & Features

    • Teardrop-shaped overlapping design
    • Snap closure

    Style Number/Barcode: 07003-0557

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetly Sheer Lace Tie Front Crop Top

    A little angel, a little trouble—this lace crop is your new fave layering piece. Style it over a bralette or solo for that effortlessly flirty, carefree vibe!

    Fit & Features

    • Sheer lace fabric
    • Long sleeves with flare cuffs
    • Tie front
    • Ultra-cropped hem
    • Bra not included
    • Runs true to size

    Style Number/Barcode: 06204-000021

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: S, M, L

  • Remarkable Energy Abstract Striped Wide-Leg Jumpsuit

    This abstract striped jumpsuit will never fail to impress! The cutout bodice adds a sassy allure while the hidden side pockets along the flattering wide-leg silhouette provide trendy convenience! 

    Fit & Features

    • Abstract striped print, woven fabric
    • Sweetheart neckline, spaghetti straps
    • Stretchy smocked back
    • Cutout bodice
    • Hidden side pockets
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06302-000001

    Category Name: Vacation Looks

    Price: $49.90

    Availability: In Stock

    Available Color: BLK/WHT

    Available Size: S, M, L, XL

  • Frill Seeker Ruffled Denim Shorts

    These denim shorts? Total heartthrob. With a mid-rise waist and ruffled hem, it’s giving playful, pretty, and just the right amount of sass for any OOTD.

    Fit & Features

    • Cotton denim fabric, no stretch
    • Mid-rise waist
    • Side zipper and hook-eye closure
    • Ruffled trim hem
    • Form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 06303-000015

    Category Name: Vacation Looks

    Price: $32.90

    Availability: In Stock

    Available Color: DARK, DENIM

    Available Size: S, M, L, XL

  • Destined For Love Lace-Up Short Skater Dress

    You'll be destined for love in this short skater dress perfect for dressy parties! This flirty dress features a square neckline, adjustable spaghetti straps, and a lace-up back for a perfect fit. The skater silhouette and short-length hem add a playful touch, while the burnout pattern on the mesh fabric adds a touch of intrigue. Complete the look in block heels.

    Fit & Features

    • Burnout pattern, mesh fabric, tulle and stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps
    • Lace-up, back zipper and hook-eye closure
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3319

    Category Name: Vacation Looks

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heart It Oversized Round Sunglasses

    You'll totally heart these trendy oversized round sunglasses! They feature a round shape with a sleek plastic frame and arms, the cutest heart-shaped cutout design accented on the arms, built-in nose pads for support, and tinted lenses. Style these shades with a charm necklace.

    Fit & Features

    • Oversized round-shape
    • Plastic frame and arms
    • Heart-shaped cutout design
    • Built-in nose pads
    • Tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1081

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glamour Steps Rhinestone Strappy Flat Sandals

    Add glamour to your steps in these faux leather flat sandals showcasing a sparkling rhinestone embellished trim, round toe, and rhinestone-embellished strappy design with an adjustable ankle strap with buckle closure. Complete the look in a casual bodycon dress for a day out and about!

    Fit & Features

    • Flat sole
    • Faux leather material
    • Round toe
    • Rhinestone trim
    • Rhinestone embellished strappy design
    • Adjustable ankle strap, buckle closure
    • Luxe fit cushioned insole
    • Runs true to size

    Style Number/Barcode: 07404-1158

    Category Name: Vacation Looks

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free