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.

  • Desert Haze Paisley Flare Pants

    These boho-chic printed flare pants are perfect for a weekend getaway! They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, a flared hem, and a trendy paisley multi-print pattern. The knit fabric offers plenty of stretch. Style with a tie-front top and booties!

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Paisley multi-print pattern
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-0944

    Category Name: Vacation Looks

    Price: $11.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Muse Lace-Up Embroidered Crop Top

    Channel that boho babe vibe in this lace embroidered crop top with a trendy lace-up front design. Style with the matching mini skirt for festival season!

    Shop Matching Bottoms: Boho Muse Lace Embroidered Mini Skirt

    Fit & Features

    • Lined sheer mesh fabric with lace embroidery
    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Front lace-up design
    • Smocked back, zipper closure
    • Fitted cropped hem
    • Runs true to size

    Style Number/Barcode: 06003-2746

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: L

    Product Badge:
    • Part of a Set
  • Sandy Beaches Palm Wide-Leg Pants

    Can't you imagine strolling the beach in these palm print pants? Embrace vacay in this tropical stunner featuring a high-rise waist, wide-leg silhouette, and back zipper closure. Complete the look with the matching top.

    Shop Matching Top: Sandy Beaches Palm Bandeau Top

    Fit & Features

    • High rise waist
    • Wide-leg silhouette
    • Back zipper closure
    • Palm print, woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0655

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oopsy Daisy Print Knit Mini Dress

    It's no mistake if this casual mini-dress makes its way into your cart! Perfect for weekend outings and day dates, this daisy print dress features a sleeveless V-neck, spaghetti straps, a center bust ruched seam for a cute scrunched look, and a bodycon silhouette. Complete the look in strappy platform sandals.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Center bust ruched seam
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy daisy print
    • Rib knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5041

    Category Name: Vacation Looks

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Timeless Love Rib Knit Maxi Dress

    You'll adore this rib knit maxi dress time and time again! Create your capsule wardrobe with this perfect dress featuring a sleeveless square neck, spaghetti straps, a curve-hugging silhouette, and a sultry side slit. Complete the look in a statement crop jacket, hoop earrings, and your go-to sneakers!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Curve-hugging silhouette
    • Side slit
    • Maxi-length hem
    • Stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4916

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine State Of Mind Off-The-Shoulder Romper

    Perfect for soaking up the sun, this off-the-shoulder romper is an effortlessly stylish option for spring! It features puff short sleeves, a ruched bust with a faux wrap look and tie-back closure, and a flowy layered short hem. Complete your flirty outfit with platform sandals.

    Fit & Features

    • Puff short sleeves, off-the-shoulder
    • Ruched bust, faux wrap with tie-back closure
    • Back zipper and hook-eye closure
    • Flowy, layered short hem
    • Shorts-lining
    • Crepe woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06403-0297

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Get That Glow Tank And Biker Shorts Set

    Get that glow in this bold seamless set that you can style up or down! It features a cropped tank with a V-neckline, spaghetti straps, and a fitted silhouette. The matching biker shorts feature a high-rise waist, a mid-thigh length hem, and a form-hugging fit. The ribbed knit fabric offers plenty of stretch. Style with a denim jacket and sneakers.

    Fit & Features

    • Matching tank and shorts set
    • Cropped tank, V-neckline, spaghetti straps
    • Biker shorts, high-rise waist, mid-thigh length, form-hugging fit
    • Seamless ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 07103-0919

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Diva Moment Cat Eye Sunglasses

    Have a total diva moment in these edgy-glam sunglasses! They feature an oversized cat eye design with a flat top and dark-tinted lenses. Style with a quilted clutch.

    Fit & Features

    • Oversized cat eye design
    • Flat top
    • Plastic frame, stud accents
    • Dark-tinted lenses
    • 100% UV protection

    Style Number/Barcode: 07008-0989

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hidden Treasure Faux Pearl Slide Sandals

    You'll truly covet these faux pearl sandals all season long! They feature a square toe, a wide single strap with faux pearls, a quilted faux leather footbed, a flat sole, and slide-on-and-off styling. Complete the look in a trendy crossbody bag.

    Fit & Features

    • Square toe
    • Faux pearl wide single strap
    • Quilted faux leather footbed
    • Flat sole
    • Slide-on-and-off styling
    • Runs true to size

    Style Number/Barcode: 07404-1083

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Day To Night Chic Crossbody Bag

    This chic crossbody bag is perfect for transitioning from day to night! It features a mini design with a top handle strap, a fold-over design with a sleek metal trim and a snap-button closure, a diamond-shaped quilted faux leather exterior, a lined interior, and a thin chain-link shoulder strap. Style with a pair of strappy mules.

    Fit & Features

    • Mini design
    • Top handle strap
    • Fold-over design, metal trim, snap-button closure
    • Diamond quilted faux leather exterior
    • Woven lined interior
    • Chain-link shoulder strap

    Style Number/Barcode: 07203-1181

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Muse Butterfly Print Flare Pants

    You'll be a dreamy muse in these trendy and fab butterfly print flare pants! They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, and a flared hem. The sheer mesh fabric features an abstract butterfly print pattern, perf for festival season! Style with an embellished crop top and clear mules.

    Fit & Features

    • High-rise elasticized waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Butterfly print
    • Sheer mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-2265

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Under The Sun Chevron Knit Sweater Top

    Let the sun kiss your shoulders in this sweater knit top for festivals, concerts, or any weekend plans! It features a sleeveless halter neckline with a tassel tie-neck closure, a fitted crop hem with tassel trim, and a sultry open-back with a tassel tie-back closure. The top is designed with a multi-colored chevron knit fabric with minimal stretch. Complete the look in flare denim jeans.

    Fit & Features

    • Sleeveless halter neckline
    • Tassel tie-neck closure
    • Fitted crop hem, tassel trim
    • Open-back, tassel tie-back closure
    • Multi-colored chevron knit
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1660

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • For The Frill Ruffled Tie-Back Skater Dress

    You'll totally be eyeing this skater dress for its frills! Have your twirl-worthy moment in this short dress featuring a square neck, short puff sleeves, a tie-back detail, and a flowy fit and flare silhouette with a tiered ruffle trim skirt. Complete the look with a trendy purse and mules for a baby shower or celebration!

    Fit & Features

    • Square neck, short puff sleeves
    • Tie-back detail
    • Flowy, fit and flare silhouette
    • Tiered ruffle trim skirt
    • Short-length hem
    • Lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4851

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Flare To Remember Skater Dress

    You'll be unforgettable in this short skater dress perfect for twirling into baby showers, brunches, and family parties! Featuring a sleeveless plunge v-neckline, spaghetti straps that cross and tie along the open back, and a fit-and-flare silhouette. The dress is composed of airy printed chiffon fabric with a smooth woven lining. Style with strappy mules and a clutch! 

    Fit & Features

    • Sleeveless plunge v-neckline
    • Spaghetti straps
    • Open back, cross strap design, tie closure
    • Fit and flare skater silhouette
    • Short-length hem
    • Airy printed chiffon fabric, smooth woven lining
    • Runs true to size

    Style Number/Barcode: 05102-4988

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winged Beauty Butterfly Sunglasses

    Adorn your outfit with whimsical beauty! These statement sunglasses feature retro-style butterfly frames with tinted lenses, side rhinestone accents, nose supports, and metal arms. Complete the look with dainty fringe earrings.

    Fit & Features

    • Retro-style butterfly frames
    • Tinted lenses
    • Side rhinestone accents
    • Nose supports, metal arms

    Style Number/Barcode: 07008-0988

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vacay Dream Floral Strappy Maxi Dress

    POV: You just entered the group chat looking like a vacay dream. This mesh maxi dress hugs in all the right places with a strappy back that turns heads on vacation and summer parties!

    Fit & Features

    • Tropical floral print, mesh-lined fabric, moderate stretch
    • V-neckline
    • Bungee spaghetti straps
    • Strappy open back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000389

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Step Espadrille Lace-Up Wedges

    These espadrille wedges will put a spring in your step! They feature a faux leather square toe, wide toe strap, and lace-up ankle straps with a supportive ankle band. Complete the look with a trendy handbag.

    Fit & Features

    • Square toe
    • Wide toe strap
    • Lace-up ankle strap with supportive band
    • Espadrille sole
    • Faux leather trim
    • Wedge heel

    Style Number/Barcode: 07406-0325

    Category Name: Vacation Looks

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Savannah High-Rise Straight-Leg Jeans by Windsor Denim

    The Savannah straight-leg jeans by Windsor Denim are a major must-have in your everyday wardrobe! They feature a high-rise waist, destructed detailing down the front, a straight-leg fit, and a subtle frayed hem. The medium-wash denim fabric features a color-faded design for a cool vintage look. Style with a crop top and mules.

    Fit & Features

    • High-rise waist
    • Destructed detailing
    • Straight-leg fit, frayed hem
    • Five-pocket and belt loop styling
    • Front button, hidden zipper closure
    • Denim fabric, color-faded design, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0414

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Polished Paperbag Shorts

    Chic and polished, these woven paperbag shorts will elevate your casual looks! They feature a high-rise paperbag waist with small slit accents at the front, a tie-front belt, front pockets, a cuffed hem, and a fitted silhouette. The smooth twill fabric offers a lightweight feel. Style with a crop top and denim jacket.

    Fit & Features

    • High-rise paperbag waist, front slit accents
    • Tie-front belt
    • Hidden front zipper, hook and bar closure
    • Dual front pockets
    • Cuffed hem, fitted silhouette
    • Woven twill fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0284

    Category Name: Vacation Looks

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • True Staple Short Skater Dress

    A true staple for daytime soirees and celebrations! This short skater dress features a classic sleeveless square neck, adjustable spaghetti straps, a tie-front bust, flexible boning inserts along the bodice, and is composed of smooth woven fabric with a stretchy knit lining. Complete the look with a bracelet and heels.

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Tie-front bust, flexible boning inserts
    • Skater silhouette
    • Short-length hem
    • Woven fabric stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2016

    Category Name: Vacation Looks

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Budding Romance Floral Chiffon Skater Dress

    Create a dreamy spring date outfit in this adorable floral chiffon skater dress! It features a square neckline, ruching at the bust, a tie-front accent and keyhole cutout, short puff sleeves, a high waist seam, and a short skater skirt with a fit and flare silhouette. The airy chiffon fabric features an all-over dainty floral print pattern for the prettiest look. Style with espadrille sandals.

    Fit & Features

    • Square neckline, ruched bust, tie-front detail, keyhole cutout
    • Short puff sleeves, elastic cinched hems
    • Back zipper, hook and eye closure
    • High waist seam, short skater skirt, fit and flare silhouette
    • Dainty floral print
    • Chiffon fabric, knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1838

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Remy High-Rise Frayed Shorts By Windsor Denim

    Pick up the phone, the Remy jean shorts by Windsor denim are calling to be your number one this season! They feature a flattering high-rise waist, front and back heavy distressed accents, and a trendy frayed cut-off hem. The shorts are composed of vintage-inspired medium-wash denim fabric with color fading. Complete the look in a crop top and cowboy boots for the perfect festival or concert outfit!

    Fit & Features

    • High-rise waist
    • Front and back heavy distressed accents
    • Frayed, cut-off hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, color fading, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0244

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachside Stroll Printed Maxi Skirt

    You'll look effortlessly pretty as you take a beachside stroll in this fab maxi skirt! It features a high-rise waist, a faux wrap-front design creating a high slit, a form-hugging fit at the hips, and a maxi-length hem with a flowy silhouette. The knit fabric features an abstract tropical print for major vacay vibes. Style with a crop top and sandals.

    Fit & Features

    • High-rise elasticized waist
    • Faux wrap-front design
    • High front slit
    • Hip-hugging fit, maxi-length hem, flowy silhouette
    • Abstract tropical print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0819

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Resort Bound Tropical Print Flare Pants

    You'll look resort-ready in these trendy tropical print flare pants! They feature a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, and a flared hem. The stretchy knit fabric features a bold tropical palm leaf print that is perfect for pairing with a basic crop top. Complete your vacay look with strappy sandals.

    Fit & Features

    • High-rise elasticized waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Tropical palm leaf print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06502-2269

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance