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.

  • Casual Trendsetter Fleece Shorts

    Keep it cute and casual in these trendy fleece shorts that will step up your loungewear! They feature a high-rise elasticized waist, side pockets, and a relaxed fit. The shorts are composed of a cozy knit fabric with a soft fleece lining and offer a moderate stretch. Complete the look with the matching cropped hoodie.

    Shop Matching Hoodie: Basic Cropped Fleece Hoodie

    Fit & Features

    • High-rise elasticized waist
    • Side pockets
    • Relaxed fit
    • Knit fabric, fleece lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-0959

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sizzling Snake Lace-Up Bodysuit

    You'll look so fire in this snake mesh bodysuit featuring a sleeveless, plunge v-neckline with lace-up closure, dual snap-button closure, and a thong-cut bottom. Complete the look in a fab mini skirt for happy hour.

    Fit & Features

    • Sleeveless, plunge v-neckline
    • Lace-up closure
    • Snake pattern
    • Dual snap button closure
    • Thong-cut bottom
    • Stretchy mesh-lined fabric
    • Fits true to size

    Style Number/Barcode: 06001-4099

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Chic Vibes Mini Skirt

    This faux suede mini skirt will elevate your everyday look and bring major chic vibes. It features a high-rise waist, a small side slit, and a short, form-hugging silhouette. Style this skirt with a cute bodysuit and strappy mules.

    Fit & Features

    • High-rise waist
    • Back zipper, hook and eye closure
    • Side slit
    • Mini-length, form-fitting silhouette
    • Smooth faux suede fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06401-0451

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summertime Chic Mesh Swim Top

    Showcase major summertime chic vibes with this tank swim top! It features a sleeveless scoop neckline, tank shoulder straps, padded cups, and dual sheer mesh inserts at the hem. Style with the matching swim bottoms.

    Shop Matching Bottoms: Summertime Chic Mesh Swim Bottoms

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Padded cups
    • Dual sheer mesh inserts at the hem
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07104-0619

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • See Ya Later Snake Twist Midi Skirt

    Tell em' boy bye! You'll be looking so fab in this snake midi skirt featuring a high-rise waist, bodycon silhouette, and a twist front accent on brushed, stretchy knit fabric. Complete the look in the matching top.

    Shop Matching Top: See Ya Later Snake Twist Crop Top

    Fit & Features

    • High-rise waist
    • Bodycon silhouette
    • Twist front accent 
    • Midi-length hem
    • Stretchy brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 06501-0627

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • See Ya Later Snake Twist Crop Top

    Tell em' boy bye! You'll be looking so fab in this snake crop top featuring long sleeves, a plunge v-neck, and a twisted bodice on brushed, stretchy knit fabric. Complete the look in sultry faux leather pants and heels. 

    Shop Matching Skirt: See Ya Later Snake Twist Midi Skirt

    Fit & Features

    • Long sleeves
    • Plunge v-neckline
    • Twisted bodice
    • Cropped hem
    • Stretchy brushed knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4071

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Standing Ovation Crepe Pleat Romper

    This crepe romper deserves a standing ovation! Featuring a sleeveless, square neck, spaghetti straps, a flirty cutout bodice atop high-waisted pleat shorts, and an open-back with bow-tie closures. Complete your grad-day look in statement earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Cutout bodice
    • High-waisted pleat shorts
    • Open-back, bow-tie closures
    • Stretch-crepe lined fabric
    • Runs true to size

    Style Number/Barcode: 06503-0975

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cutest Ever Flutter Sleeve Mini Dress

    This airy chiffon mini dress designed with short flutter sleeves and a flowy A-line silhouette would be the cutest brunch style! You'll adore the subtle swiss dot pattern and dainty lace trim hem.

    Fit & Features

    • Sheer chiffon fabric, swiss dot pattern, woven lining, lace trim
    • Sleeveless scoop neckline, ruched bust
    • Adjustable spaghetti straps, flutter sleeve accent
    • Back zipper closure, tie-back design
    • Mini-length A-line silhouette, pleating
    • Runs true to size

    Style Number/Barcode: 05101-000078

    Category Name: Vacation Looks

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Chic Peasant Sleeve Top

    Achieve that charming chic look with this adorable peasant sleeve top. It features a sweetheart neckline, long sleeves with tapered hems, a triple tie-front design, and a cropped, form-hugging fit. Pair this top with vintage-style jeans.

    Fit & Features

    • Sweetheart neckline, ruching at the bust
    • Long peasant sleeves, tapered hems, triple button detailing
    • Triple tie-front design
    • Stretchy smocked back
    • Cropped, form-hugging fit
    • Lightweight woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-1706

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • May Flowers Crepe Tie-Front Top

    You'll be blooming for spring in this crepe floral top featuring long peasant sleeves, a plunge v-neckline with tie-front detail, a drawstring waist, and a ruffled hem. Complete the look in trendy high-rise jeans and sandals.

    Fit & Features

    • Long peasant sleeves
    • Plunge v-neckline
    • Tie-front detail
    • Drawstring waist
    • Ruffled hem
    • Floral pattern
    • Crepe fabric, no stretch, fits true to isze

    Style Number/Barcode: 06204-1149

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Needed Cutout Tank Top

    A one-shoulder tank top like this is always needed to create eye-catching looks! Featuring a sleeveless, one strap design, and a sultry side cutout with a drawstring so you can customize the fit. Composed of stretchy rib-knit fabric. Finish the look in jeans.

    Fit & Features

    • Sleeveless, one-shoulder strap design
    • Side cutout, adjustable drawstring
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06001-4077

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vineyard Floral Slit Maxi Dress

    Wine tasting anyone? This floral maxi is perfect for sipping on your fav red or white! It features a sleeveless, off-the-shoulder neckline, a form-fitting silhouette, and dual front slits for a sultry show of leg. Complete the look in wedges and a floppy hat.

    Fit & Features

    • Sleeveless, off-the-shoulder neckline
    • Flutter sleeve cuffs
    • Form-fitting silhouette
    • Dual front slits, maxi-length hem
    • Floral pattern
    • Stretch-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4554

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Style Refresh Tie Waist Crop Top

    Give your basics a refresh in this stylish tank top featuring a sleeveless, high neck, and a tie-waist design on the cropped hem. Composed of soft and stretchy fabric. Finish the look in sleek leggings and booties.

    Fit & Features

    • Sleeveless, high neck
    • Tie-waist design
    • Cropped hem
    • Soft and stretchy fabric
    • Runs true to size

    Style Number/Barcode: 06001-4083

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Sun Crepe Knit Midi Dress

    Bare your shoulders in this floral midi dress for brunch with the girls! Featuring spaghetti straps, a sweetheart neckline, and a front slit accent on crepe knit fabric with a moderate stretch. Complete the look in heeled mules and hoops.

    Fit & Features

    • Sleeveless, spaghetti straps
    • Sweetheart neckline, slit accent
    • Floral print
    • Midi hem
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4305

    Category Name: Vacation Looks

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • That Preppy Vibe Houndstooth Blazer

    Haven't you heard? That preppy vibe is so trendy this season! Create a cute look in this houndstooth plaid blazer featuring long sleeves, a collared neckline, an open-front with dual button closure, and flap pockets. Complete the look in the matching shorts.

    Shop Matching Shorts: That Preppy Vibe Houndstooth Shorts

    Fit & Features

    • Long sleeves
    • Collared neckline
    • Open-front, dual button closure
    • Flap pockets
    • Cropped hem
    • Houndstooth plaid pattern
    • Woven-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1316

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • That Preppy Vibe Houndstooth Shorts

    Haven't you heard? That preppy vibe is so trendy this season! Create a cute look in this houndstooth plaid blazer featuring long sleeves, a collared neckline, an open-front with dual button closure, and flap pockets. Complete the look in the matching shorts.

    Shop Matching Blazer: That Preppy Vibe Houndstooth Blazer

    Fit & Features

    • High-rise waist
    • Front button closure, belt loop accents
    • Pleat detailing
    • Form-fitting silhouette
    • Houndstooth plaid pattern
    • Woven-lined fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0221

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Layers Of Rhine Anklet

    Polish off your look in this rhinestone anklet featuring a layered design with a lobster clasp closure. Complete the look in a chic two-piece set.

    Fit & Features

    • Layered design
    • Rhinestones
    • Lobster clasp closure

    Style Number/Barcode: 07003-0338

    Category Name: Vacation Looks

    Price: $2.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High-Rise Destructed Ankle Jeans

    These high-rise destructed ankle jeans are perfect for styling with your everyday 'fits. They feature a high-rise waist, fading down the leg, destructed detailing at the knees, and a frayed ankle-cut hem. Style these jeans with a cute tie-front top and mules.

    Fit & Features

    • High-rise waist
    • Fading down the leg, destructed detailing at the knees
    • Frayed ankle-cut hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Dark wash denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06602-0297

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Meli Mid-Rise Cuffed Denim Shorts by Windsor Denim

    The Meli mid-rise jean shorts by Windsor Denim are the perfect pair for the spring and summer seasons! They feature a fitted waist, light destructed detailing, and a stylish frayed and cuffed hem. The dark wash denim fabric offers a moderate stretch for comfortable wear. Complete the look with your fave sandals.

    Fit & Features

    • Mid-rise waist
    • Light distressing
    • Frayed and cuffed hem
    • Five-pocket and belt loop design
    • Front button, hidden zipper closure
    • Dark wash denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06603-0227

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Geometric Fun Cutout Mini Dress

    This mini dress requires no math skills! Features a sleeveless V-neckline, spaghetti straps, bodycon silhouette, and a flirty front cutout bodice with ruched detail. Composed of geometric print fabric. Finish the look in strappy heels.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Bodycon silhouette
    • Front cutout, ruched detail
    • Mini-length hem
    • Adjustable drawstrings
    • Geometric print, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4350

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Skip A Beat Halter Ruched Crop Top

    Make every heart skip a beat! This trendy halter crop top features a sleeveless high neck, tie-back closure, and ruched seams that accentuate your curves on the stretchy rib-knit fabric. Complete the look in cute shorts.

    Fit & Features

    • Sleeveless, high neck, halter
    • Tie-back closure
    • Cropped hem
    • Ruched seams
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06001-4198

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Butterfly Effect Rimless Square Sunglasses

    Giving fairycore with a side of don’t talk to me. These rimless tinted lenses and butterfly accents are straight-up magical for brunch, beach, or bossing up.

    Fit & Features

    • Rimless square tinted lenses
    • Delicate butterfly accents on frame corners
    • Lightweight plastic arms
    • Nose support pads

    Style Number/Barcode: 07008-000014

    Category Name: Vacation Looks

    Price: $10.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

  • Edgy Deets Lace-Up Shorts

    You'll love the edgy details of these crepe shorts that are perf for festival season. They feature a high-rise waist, lattice designs down the sides, and a semi-cheeky, form-hugging fit. Style these shorts with a crop top and booties.

    Fit & Features

    • High-rise waist
    • Lattice designs down the sides, tie closures
    • Semi-cheeky, form-hugging fit
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-0962

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forget The Drama Sleeveless Jumpsuit

    Keep it laid back in a jumpsuit that brings on those cool-girl vibes. The jumpsuit features a sleeveless square neckline, adjustable spaghetti straps, and culotte-styled pants. The jumpsuit is composed of a lined lightweight woven fabric that offers a loose fit with a minimal stretch. Complete look with a cute boater hat and mules for a fab day out!

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Culotte-styled pants
    • Oversized fit, minimal stretch
    • Lined lightweight woven fabric
    • Runs true to size

    Style Number/Barcode: 06302-0650

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance