Vacation Looks

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STYLE SPOTLIGHT

Discover Short Sleeve Dresses

Capture On-Trend Sundresses

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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.

  • Miami Nights One-Shoulder Crop Top

    Bring the heat and take on the night scene in this alluring crop top! It features a sleeveless asymmetric one-shoulder neckline with a single spaghetti strap, ruched detailing, and a fitted cropped hem. The lined mesh fabric offers plenty of stretch. Style with the matching mini skirt and a pair of strappy stilettos.

    Shop Matching Bottoms: Miami Nights Ruched Mini Skirt

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Single adjustable spaghetti strap
    • Ruching
    • Fitted cropped hem
    • Sheer mesh fabric, full knit lining
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06001-4672

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Find Lace-Up Cork Block Heels

    Embrace the warmer months with these cork block heels that are the cutest find! They feature an open almond-shaped toe, a thin strappy design across the foot, a heel strap, a thin lace-up strappy design that wraps around the leg, and a cork block heel. Style with a mini handbag.

    Fit & Features

    • Open almond-shaped toe
    • Thin strappy design across the foot
    • Heel strap
    • Thin strappy lace-up wrap-around design, tie closure
    • Cork block heel
    • Faux leather insole and straps
    • Runs true to size

    Style Number/Barcode: 07401-4315

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Glam Rhinestone And Pearl Sandals

    These effortless glam embellished sandals are a perfect pick for the summer season! They feature a square-shaped toe, dual clear straps with pearl embellishments, a two-row rhinestone outline along the flat sole, and an open back for easy on-and-off styling. Pair these sandals with a mini handbag.

    Fit & Features

    • Square-shaped toe
    • Dual clear PVC straps
    • Pearl embellishments
    • Two-row rhinestone outline, flat sole
    • Open back
    • Runs true to size

    Style Number/Barcode: 07404-1108

    Category Name: Vacation Looks

    Price: $12.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready For It Faux Leather Lace-Up Wedges

    You'll be ready for a fabulous night out in these bold lace-up wedges! They feature an open almond-shaped toe with a strap, thin criss-cross straps across the foot, a heel strap, thin lace-up straps that wrap around the leg, and a tall, sturdy wedge heel. Style with a chic crossbody bag.

    Fit & Features

    • Open almond-shaped toe, strap
    • Thin criss-cross straps across the foot
    • Heel strap, thin lace-up straps
    • Wrap-around design, tie closure
    • Tall wedge heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-0334

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute Factor Eyelet Lace Skater Dress

    Bring the cute factor by wearing this eyelet lace skater dress for picnics, brunch, or casual family parties! Featuring adorable puff short sleeves, a square neck with a ruched bust, a flirty tie-back closure, and a fit-and-flare silhouette and short hem. Complete the look with cute flower earrings.

    Fit & Features

    • Puff short sleeves
    • Square neck, ruched bust
    • Tie-back closure
    • Skater, fit and flare silhouette
    • Short-length hem
    • Eyelet lace fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4910

    Category Name: Vacation Looks

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • My Favorite Chiffon Floral Crop Top

    This chiffon crop top will be your favorite for day dates or coffee with friends! It features dreamy sheer peasant sleeves, a sweetheart neckline, a twisted bust, a stretchy smocked back, and an ultra-cropped hem. Style with high-rise jeans and sandals to complete the look!

    Fit & Features

    • Sheer peasant long sleeves
    • Sweetheart neckline, twisted bust
    • Ultra cropped hem
    • Stretchy smocked back
    • Blooming floral print
    • Lined airy chiffon
    • Runs true to size

    Style Number/Barcode: 06003-2151

    Category Name: Vacation Looks

    Price: $4.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Quick Instinct Zebra Print Mesh Flare Pants

    If your instincts lead to these zebra print flare pants...they belong in your cart! Featuring a high-rise waist, a hip-hugging fit, a form-hugging fit throughout the legs, and a flared hem on a mesh fabric. Complete the look with the matching bustier.

    Shop Matching Top: Quick Instinct Zebra Print Mesh Bustier

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Form-hugging fit throughout the legs
    • Flared hem
    • Zebra print
    • Mesh fabric
    • Runs true to size

    Style Number/Barcode: 06502-2257

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Quick Instinct Zebra Print Mesh Bustier

    If your instincts lead to this zebra print bustier...it belongs in your cart! Featuring a strapless and structured bodice with flexible boning, a pointed crop hem, and a back zipper and hook-eye closure on a lined mesh fabric. Complete the look with the matching flare pants.

    Shop Matching Bottoms: Quick Instinct Zebra Print Mesh Flare Pants

    Fit & Features

    • Strapless and structured bodice
    • Flexible boning
    • Pointed crop hem
    • Back zipper and hook-eye closure
    • Zebra print
    • Lined mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4742

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Breezy Chic Crochet Trim Kimono

    Layer on this breezy and chic kimono to elevate every outfit! It features short sleeves, an open-front design, a back crochet trim, and a flowy long hem. Complete the look in flat sandals for a boho style!

    Fit & Features

    • Short sleeves
    • Open front design
    • Back crochet trim
    • Flowy hem
    • Lightweight woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1586

    Category Name: Vacation Looks

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Switch It Up Wayfarer Oversized Sunglasses

    Switch up your style this season in these wayfarer sunglasses perfect for wearing on beach days or at pool parties! They feature an oversized design, pink frames with sleek metal arms, and tinted pink lenses. Complete the look in a sassy matching set.

    Fit & Features

    • Oversized design
    • Sleek metal arms
    • Pink frame
    • Tinted pink lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1007

    Category Name: Vacation Looks

    Price: $3.96 $9.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Road Trippin' Classic Aviator Sunglasses

    Slip on these classic aviator sunglasses during your next road trip or beach day! They feature a sleek design, a metal frame, rubber nose supports, and tinted brown lenses to help protect your eyes from the sun. Complete the look in a trendy crop denim jacket.

    Fit & Features

    • Sleek design
    • Metal frame
    • Rubber nose supports
    • Tinted brown lenses
    • 100% UV protection

    Style Number/Barcode: 07008-1004

    Category Name: Vacation Looks

    Price: $3.96 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Playful Touch Crepe Daisy Print Short Dress

    Add a playful touch to your closet with this adorable crepe daisy print dress to wear for birthdays or family parties! It features puff short sleeves, a sweetheart neckline, a flirty bust tie, a stretchy smocked back, hidden side pockets for keeping your hands warm, and a tiered ruffled short-length hem. Complete the look with dainty earrings.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neckline
    • Bust tie front, stretchy smocked back
    • Hidden side pockets
    • Tiered ruffled short-length hem
    • Daisy print, 

    Style Number/Barcode: 05101-2338

    Category Name: Vacation Looks

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Subtle Love Ditsy Floral Mini Dress

    Effortlessly cute with subtle detail, what's not to love about this ditsy floral mini dress? It features a sleeveless V-neckline with a ruched bust seam, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a brunch.

    Fit & Features

    • Sleeveless V-neckline, ruched bust seam
    • Spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Ditsy floral print
    • Ribbed stretchy knit fabric, knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5073

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can't Resist Chiffon Floral Skater Dress

    No one can resist you in this chiffon floral dress - a staple for all of the upcoming soirees! It features a sleeveless V-neckline, adjustable spaghetti straps, a tie-back closure, and a flattering skater short silhouette. Complete the look in faux leather mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Tie-back closure
    • Skater silhouette
    • Short-length hem
    • Floral print, chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2057

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Drink Tequila Graphic Tee

    Get ready to go to happy hour with your squad in the cutest graphic tee! It features a crew neckline with a side cutout, short sleeves, a front agave and limes graphic with the script "Time To Drink Tequila," a mid-length hem, and a relaxed fit. The cotton fabric offers a moderate stretch. Style with denim shorts and strappy sandals.

    Fit & Features

    • Crew neckline, side cutout
    • Short sleeves
    • Agave and limes graphic
    • Script that reads, "Time To Drink Tequila"
    • Mid-length hem, relaxed fit
    • Cotton fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1558

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay On My Mind Floral Mini Skirt

    You'll be ready for your vacay getaway with this bold floral mini skirt. It features a high-rise waist, dual vertical seams down the front, all-over ruching, a mini-length hem, and a curve-hugging silhouette. The lined mesh fabric features a tropical floral print pattern. Style with the matching bustier and a pair of mules!

    Shop Matching Top: Vacay On My Mind Floral Bustier Top

    Fit & Features

    • High-rise elasticized waist, back zipper, hook and eye closure
    • Dual vertical seams down the front
    • All-over ruching
    • Mini-length hem, bodycon fit
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06501-0791

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay On My Mind Floral Bustier Top

    You'll be ready for your vacay getaway with this bold floral bustier top. It features a sleeveless sweetheart neckline, adjustable spaghetti straps, a corset-designed bodice with ruching at the bust, and a fitted, cropped hem. The mesh fabric features a tropical floral print pattern. Style with the matching mini skirt and a pair of mules!

    Shop Matching Bottoms: Vacay On My Mind Floral Mini Skirt

    Fit & Features

    • Sleeveless sweetheart neckline, padded cups
    • Adjustable spaghetti straps
    • Corset-designed bodice, ruched bust
    • Fitted, cropped hem
    • Tropical floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4714

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Seriously Stylish Satin Trouser Pants

    These satin trouser pants are seriously stylish for working babes and after-hours fun! They feature a flattering high-rise waist, hidden side pockets, and a wide-leg silhouette. Complete the look in a sleeveless top and strappy sandals. 

    Fit & Features

    • High-rise waist
    • Hidden side pockets
    • Side zipper closure
    • Wide-leg silhouette
    • Silky satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06402-1281

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Start Your Engines Slash Graphic Crop Tee

    Start your engines and rev up in edgy style by showcasing this graphic crop tee! It features short sleeves, a crew neck, a front graphic with "Custom Parts Classic Motors" and a slashed cropped hem. Complete the look in trendy denim jeans for a concert or chilling with friends!

    Fit & Features

    • Short sleeves
    • Crew neck
    • Front graphic and script, "Custom Parts Classic Motors"
    • Slashed cropped hem
    • Stretchy cotton fabric
    • Runs true to size

    Style Number/Barcode: 06002-1555

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Beauty Ditsy Floral Romper

    Keep it sweet in this gorg romper that is perf for your next date night! The romper features a sleeveless square neckline, spaghetti straps, a ditsy floral print, a lower back keyhole cutout with tie-back straps, and wide-leg shorts with a tiered skater overlay.  Complete the look with sandals.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print
    • Lower back keyhole cutout, tie-back straps
    • Wide-leg shorts
    • Tiered skater overlay, fit and flare silhouette
    • Woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06403-0276

    Category Name: Vacation Looks

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Classic Chic Vibes Paperbag Romper

    Bring those classic and chic vibes to your look with this stylish romper! It features a sleeveless V-neckline, adjustable spaghetti straps, a high-rise paperbag waist, a tie-front belt, and a fitted silhouette. Complete the outfit with a layered necklace and heeled mules.

    Fit & Features

    • V-neckline
    • Adjustable spaghetti straps
    • High-rise paperbag waist, tie-front belt
    • Hidden side zipper and hook and eye closure
    • Side pockets
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0218

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go-Getter Gal Zebra Print Wrap Tie Top

    Amp up your business casual fits' or everyday style with this zebra print top to create stylish looks for the girls on the go! The top features peasant long sleeves with dual button cuffs, a V-neckline, surplice bodice with a wrap-tie cropped hem on smooth woven fabric. Complete the look in straight-leg jeans, heels, and a mini tote.

    Fit & Features

    • Peasant long sleeves, dual button cuffs
    • V-neckline
    • Surplice bodice
    • Wrap-tie cropped hem
    • Zebra print
    • Smooth woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1997

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Total Jetsetter Swirl Print Flare Pants

    Whether you're jet-setting to an island resort or road-tripping up to a music festival, these swirl print flare pants are just the ticket to make a stylish entrance! They feature a high-rise waist, hip-hugging fit, and a flared hem on brushed stretchy knit fabric. Complete the look in a cute corset top.

    Fit & Features

    • High-rise waist
    • Hip-hugging fit
    • Flared hem
    • Swirl print
    • Brushed stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-2246

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Weekend Ready High-Rise Denim Mom Shorts

    You'll be ready for casual weekend plans with these trendy denim mom shorts. They feature a super high-rise waist with a front button and hidden zipper closure, rolled hems, and a relaxed fit. The denim fabric offers a rigid fit with no stretch. Style with a graphic tee and sandals.

    Fit & Features

    • Super high-rise waist
    • Front button, hidden zipper closure
    • Five-pocket and belt loop design
    • Rolled hems
    • Relaxed fit
    • Denim fabric, rigid fit, no stretch
    • Runs true to size

    Style Number/Barcode: 06603-0351

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance