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.

  • Casual Plans Rib Knit Bodycon Maxi Dress

    Casual plans? Look amazing in this sleeveless maxi dress for everything on your social calendar! It features a square neckline, spaghetti straps, a bodycon silhouette, and a fitted long hem on stretchy rib knit fabric. Complete the look in cute flower earrings and sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Maxi, fitted long-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5195

    Category Name: Vacation Looks

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slice Of Summer V-Neck Tank Maxi Dress

    Break yourself off a slice of this summer-ready rib knit maxi dress you'll love taking on vacation or around town! It features a sleeveless plunge V-neckline, tank shoulder straps, a form-hugging slim silhouette, and a sexy high-side slit. Complete the look with statement earrings and sandals.

    Fit & Features

    • Sleeveless plunge V-neckline
    • Tank shoulder straps
    • Form-hugging, slim silhouette
    • High side slit
    • Maxi-length hem
    • Soft and stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5080

    Category Name: Vacation Looks

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coolness In Check Oversized Chain Sunglasses

    Keep your coolness in check with these oversized sunglasses perfect for everyday styling! They feature square-shaped plastic frames, tinted lenses, and chain-link accented arms. Complete the look in sleek large hoop earrings.

    Fit & Features

    • Square-shaped oversized plastic frames
    • Tinted lenses
    • Chain-link accented arms

    Style Number/Barcode: 07008-1014

    Category Name: Vacation Looks

    Price: $3.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Trendy Charm Choker Necklace Set

    Layer on these trendy charm choker necklaces for a casual glam look this summer! The set features three separate choker necklaces with varying designs including faux pearl beading, a faux pearl beaded flower accent, and mini-hanging coin charms. Includes back adjustable chains and lobster clasp closures. Style with a cute ring pack.

    Fit & Features

    • Three-pack choker necklace set
    • Faux pearl beading
    • Faux pearl beaded flower accent
    • Mini-hanging coin charms
    • Adjustable chains, lobster clasp closures

    Style Number/Barcode: 07002-1505

    Category Name: Vacation Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Swept Away Gauze Tie-Front Top

    Let this tie-front top sweep you away somewhere sweet this summer! It features peasant long sleeves, a plunging neckline, a tie-front closure, and a cropped hem on leaf-printed gauze woven fabric. Complete the look with a boho necklace.

    Fit & Features

    • Peasant long sleeves
    • Plunging neckline
    • Tie-front closure
    • Cropped hem
    • Leaf print
    • Gauze woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1581

    Category Name: Vacation Looks

    Price: $4.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dream Big Butterfly Chain Belt

    Build your dream look by accessorizing with this statement chain belt featuring an eye-catching butterfly design with a back adjustable chain and a lobster clasp closure. Style with a flirty ruffled romper for a summer party!

    Fit & Features

    • Butterfly design
    • Back adjustable chain, lobster clasp closure

    Style Number/Barcode: 07301-0634

    Category Name: Vacation Looks

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coastal Drive Linen Wide-Leg Cargo Pants

    The cute and casual vibes of these linen-blend wide-leg cargo pants are perfect for a drive up the coast! They feature a high-rise waist with a back elastic waistband, front pockets, large cargo-style side pockets, a wide-leg silhouette with a cuffed hem, and an overall relaxed fit. Style with a crop top and sandals.

    Fit & Features

    • High-rise waist, back elastic waistband
    • Belt loops, hidden front zipper, button closure
    • Dual front pockets, dual large cargo-style side pockets
    • Wide-leg silhouette, cuffed hem
    • Relaxed fit
    • Linen-blend fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06302-0779

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Weekend Style Denim Skort

    Level up your casual summer weekend style with this on-trend denim skort. It features a high-rise waist, a short asymmetric wrap-front overlay with button detailing, front and back pockets, and a fitted silhouette. Pair with a basic bodysuit and strappy sandals.

    Fit & Features

    • High-rise waist
    • Short asymmetric wrap-front overlay
    • Button detailing
    • Belt loops
    • Dual front and back pockets
    • Denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0339

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Darling Ditsy Floral Flowy Shorts

    Create a sweet look that is oh-so-darling with these ditsy floral printed shorts! They feature a high-rise waist, a back zipper closure, and a flowy, relaxed silhouette. The lightweight woven fabric features an adorable dainty ditsy floral print pattern. Style with the matching crop top for the perfect brunch outfit.

    Shop Matching Top: So Darling Ditsy Floral Puff Sleeve Crop Top

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Flowy, relaxed fit
    • Ditsy floral print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0225

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Darling Ditsy Floral Puff Sleeve Crop Top

    Create a sweet look that is oh-so-darling with this disty floral printed crop top! It features a sweetheart neckline with a twist-front design at the bust, short puff sleeves with ruffled trims, tie-back straps, and a fitted, cropped hem. The lightweight woven fabric features an adorable dainty ditsy floral print pattern. Style with the matching flowy shorts for the perfect brunch outfit.

    Shop Matching Bottoms: So Darling Ditsy Floral Flowy Shorts

    Fit & Features

    • Sweetheart neckline, twist-front design at the bust
    • Short puff sleeves, elasticized hems, ruffled trims
    • Tie-back straps
    • Fitted, cropped hem
    • Ditsy floral print
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1797

    Category Name: Vacation Looks

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Occasion Satin Collared Button-Down Romper

    Make your next party a chic occasion in this silky sleek satin romper! It features a collared neckline, short sleeves, a button-down front, buttoned chest pockets, a cinched waist with a faux tie-front design, front pockets, and relaxed-fitting shorts. The smooth satin woven fabric gives off a stunning sheen to amp up the chic factor. Style with a chunky chain-link necklace and clear mules.

    Fit & Features

    • Collared neckline, short sleeves
    • Button-down front
    • Dual buttoned chest pockets
    • Cinched high waist, faux tie-front
    • Dual front pockets, relaxed-fitting shorts
    • Silky satin woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0334

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Just Spotted Leopard Lace-Up Midi Dress

    Just spotted, you in this effortlessly fierce leopard print midi dress! It features a sleeveless V-neckline with a twisted bust accent, spaghetti straps that lace up in the back, and a flattering A-line silhouette with a flowy hem. Complete the look with a sleek choker for lunch with friends!

    Fit & Features

    • Sleeveless V-neckline, twisted bust accent
    • Spaghetti straps, lace-up back
    • A-line silhouette
    • Flowy midi-length hem
    • Leopard print, breezy woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4976

    Category Name: Vacation Looks

    Price: $10.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • What A Girl Wants V-Neck Mini Dress

    What a girl wants is this casual mini dress perfect for styling up or down! The dress features a sleeveless V-neckline, wide shoulder straps, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in stunning lace-up heels for a party.

    Fit & Features

    • Sleeveless V-neckline
    • Wide shoulder straps
    • Bodycon silhouette
    • Mini-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5100

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easy Decision V-Neck Cutout Maxi Dress

    A maxi dress you can style up or down? That's an easy decision! It features a sleeveless V-neckline, spaghetti straps, a knotted bust with cutout sides and back, and a hip-hugging slim silhouette with a sultry high-side slit on stretchy rib knit fabric. Complete the look in trendy sandals for a beach club or vacation!

    Fit & Features

    • Sleeveless V-neckline, knotted bust, spaghetti straps
    • Side and back cutouts
    • Hip-hugging, slim silhouette
    • High side slit
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5094

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Strut Lace-Up Platform Block Heels

    Showcase a chic strut in these cool-girl platform block heels. They feature an open square-shaped toe, a thin strappy design with knotted accents, lace-up straps that wrap around the leg, a platform sole, and a chunky block heel. Style with a mini handbag.

    Fit & Features

    • Open square-shaped toe
    • Thin strappy design, knotted details
    • Lace-up strappy wrap-around design, tie closure
    • Open back
    • Platform sole, thick block heel
    • Faux leather material, subtle cushioned insole
    • Runs true to size

    Style Number/Barcode: 07401-4240

    Category Name: Vacation Looks

    Price: $29.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • For A Spin Rhinestone Spiral Flat Sandals

    Take these luxe sandals out for a glamorous spin! Day or night, they're perfect for a classic GNO, wedding, or semi-formal event. Featuring a square toe, metallic flat sole with mini rhinestone trim, thin toe rhinestone straps, and a spiral ankle strap with rhinestone embellishments. Complete the look with a clutch purse.

    Fit & Features

    • Square toe
    • Metallic flat sole, mini rhinestone trim
    • Thin toe rhinestone straps
    • Spiral ankle rhinestone strap
    • Runs true to size

    Style Number/Barcode: 07404-1148

    Category Name: Vacation Looks

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Best Vibes Mid-Rise Denim Skort

    Give off the best style vibes in this breezy denim skort perfect for casual summer plans! It features a flattering mid-rise waist, a bodycon silhouette, a skirt-like front design, and a short-length hem on stretchy medium wash denim. Complete the look in a basic tank top and sandals.

    Fit & Features

    • Mid-rise waist
    • Bodycon silhouette
    • Skirt-like front design, short-length hem
    • Front dual button and hidden zipper closure
    • Three-pocket styling, belt loop accents
    • Medium wash denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06603-0337

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coastal-Chic Woven Straw Belt

    Accessorize your summer looks with this on-trend belt for a coastal-chic vibe. It features a woven straw design with a round buckle. Style with a crop top and distressed denim shorts.

    Fit & Features

    • Woven straw design
    • Round metal buckle

    Style Number/Barcode: 07301-0635

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Alert Cutout High Slit Mini Dress

    Get ready to flirt up a storm in this cutout high slit mini dress that will bring that sultry allure. It features a sleeveless square neckline, spaghetti straps, an asymmetric side cutout at the waist to show off some skin, a mini-length hem with a high-cut side slit, and a fitted A-line silhouette. The brushed knit fabric offers plenty of stretch. Style with lace-up heels for a night out.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Asymmetric side cutout at the waist
    • Mini-length hem, high-cut side slit
    • Fitted A-line silhouette
    • Double-lined brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-5045

    Category Name: Vacation Looks

    Price: $5.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stripe It Right Crepe Tie-Front Crop Top

    Trend right with this breezy striped crepe top essential for summer! It features bell long sleeves, a plunge V-neckline, and a flirty tie-front closure along the ultra-cropped hem. Complete the look in high-waisted jeans for exploring a beach city.

    Fit & Features

    • Bell long sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Ultra cropped hem
    • Striped print
    • Crepe fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1348

    Category Name: Vacation Looks

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 2000s Babe Rhinestone Denim Bucket Hat

    Channel that 2000s babe energy with this trendy denim bucket hat! It features a classic bucket hat design with a wide brim and all-over mini rhinestone embellishments for a stylish sparkle. Pair with a graphic tee and low-rise jeans!

    Fit & Features

    • Classic bucket hat design
    • Wide brim
    • Mini rhinestones
    • Denim material

    Style Number/Barcode: 07302-1460

    Category Name: Vacation Looks

    Price: $4.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Whimsical Beauty Butterfly Layered Necklace Set

    Adorn your semi-formal dress with this whimsical necklace set! It features a layered design with a butterfly charm, dainty flower charms, and multi-colored beads. Complete the look in a flirty skater dress for a rehearsal dinner or celebration!

    Fit & Features

    • Layered necklace
    • Butterfly charm
    • Dainty flower charms
    • Multi-colored beads
    • Sleek chain link string
    • Losber clasp closure

    Style Number/Barcode: 07002-1504

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Perfect Basic Knit Mini Dress

    This casual knit mini dress is the perfect basic for creating cute everyday 'fits! It features a V-neckline, short fitted sleeves, a mini-length hem, and a form-hugging fit. The cotton-blend fabric offers a moderate stretch. Style with hoop earrings and strappy mules.

    Fit & Features

    • V-neckline
    • Short fitted sleeves
    • Mini-length hem
    • Form-hugging fit
    • Cotton-blend smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5050

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Stroll Rib Knit Midi Dress

    Take a casual stroll looking cute in this rib knit midi dress essential for afternoon pick-me-ups with the girls! Featuring a sleeveless square neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the hem. Complete the look with a layered choker necklace.

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Form-hugging silhouette
    • Front slit
    • Midi-length hem
    • Rib knit fabric, bust lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5183

    Category Name: Vacation Looks

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale