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.

  • So Obsessed Strappy Platform Sandals

    You'll be so obsessed with these edgy-chic platform sandals! They feature a square toe, a double-banded strap design, an adjustable ankle strap, a heel strap, and a flat platform sole. Style these sleek faux leather sandals with a crossbody bag.

    Fit & Features

    • Square-shaped toe
    • Double-banded strap design
    • Adjustable ankle strap, buckle detail
    • Heel strap
    • Flat platform sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1113

    Category Name: Vacation Looks

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring It One Lace Ruffle Strap Mini Dress

    Put a spring in your step in this lace mini dress for an adorable party look! It features a sleeveless square neckline, half ruffled straps and half adjustable spaghetti straps, an open back with a tie closure, a side pleated seam, and a bodycon silhouette with an asymmetrical wrap hem. Complete the look with a dainty necklace for a bridal shower or graduation!

    Fit & Features

    • Sleeveless square neck
    • Half ruffled straps, half adjustable spaghetti straps
    • Open back with tie closure
    • Side pleated seam, bodycon silhouette
    • Asymmetrical wrap mini-length hem
    • Lace fabric, stretchy knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2142

    Category Name: Vacation Looks

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Heart Eyes Statement Sunglasses

    You'll have major heart eyes for these adorable statement sunglasses! They feature heart-shaped pink-tinted lenses with a dripping design, sleek metal arms, and rubber nose pads for support. Style with hoop earrings for a cool summer festival look.

    Fit & Features

    • Heart-shaped pink-tinted lenses
    • Dripping design
    • Thin metal arms
    • Rubber nose pads

    Style Number/Barcode: 07008-1017

    Category Name: Vacation Looks

    Price: $4.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Essential Mesh Long Kimono

    Bring it back to basics with cute layered looks with a flowy kimono! The kimono features a draped open front, long kimono sleeves, and a flowy long length. The kimono is composed of a sheer mesh fabric that offers a relaxed fit with a moderate stretch. Complete the look with a mini dress and sandals.

    Fit & Features

    • Draped open front
    • Long kimono sleeves
    • Flowy long length 
    • Sheer mesh fabric
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06202-0382

    Category Name: Vacation Looks

    Price: $4.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Beauty Smocked Bra Top

    This adorable bra top is a must-have for a beachside vacay. It features a sleeveless sweetheart neckline, adjustable spaghetti straps for a customized fit, an all-over-smocked design, and a fitted cropped hem. Style with the matching button-down top and distressed denim shorts for a casual summer vibe.

    Shop Matching Top: Beachside Beauty Button-Down Top

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • All-over stretchy smocked design
    • Fitted cropped hem
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 06003-2120

    Category Name: Vacation Looks

    Price: $3.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beachside Beauty Button-Down Top

    This adorable button-down top is a must-have for a beachside vacay. It features a collared neckline, long sleeves with buttons to cuff, a complete button-down front, and a relaxed fit. Style with the matching bra top and distressed denim shorts for a casual summer vibe.

    Shop Matching Top: Beachside Beauty Smocked Bra Top

    Fit & Features

    • Collared neckline
    • Long sleeves, single buttons to cuff
    • Button-down front
    • Relaxed fit
    • Smooth woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-2121

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Cool Crew Neck Mini Dress

    Keep it cool and casual in this effortless knit mini dress for hangs with friends! It features short sleeves, a crew neck, a bodycon silhouette, and a ruched drawstring that lets you customize the style. The dress is composed of a stretchy brushed knit fabric. Complete the look in cute flat sandals.

    Fit & Features

    • Short sleeve, crew neck
    • Bodycon silhouette
    • Ruched, adjustable drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4856

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flaunt It Girl V-Neck Twist Crop Top

    Flaunt your cute self in this crop top featuring short sleeves, a V-neck, a twisted bodice, and a fitted hem on stretchy rib fabric. Style with high-rise pants to complete the look for a lunch with friends!

    Fit & Features

    • Short sleeves
    • V-neck
    • Twisted bodice
    • Crop fitted hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-4816

    Category Name: Vacation Looks

    Price: $4.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Summer Style Wrap Midi Skirt

    Show off a breezy boho summer style with this lightweight woven midi skirt. It features a high-rise waist with a side knot detail, a wrap silhouette creating a subtle front slit, a midi-length hem, and a relaxed fit. The woven fabric features a bohemian-inspired diamond multi-print pattern. Complete the look with a basic bodysuit and strappy sandals.

    Fit & Features

    • High-rise waist, side knot detail
    • Back zipper closure
    • Wrap silhouette, front slit
    • Midi-length hem, relaxed fit
    • Bohemian-inspired diamond multi-print pattern
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06301-0164

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Remy High-Rise Lace-Up Shorts by Windsor Denim

    Spice up the denim scene in the Remy shorts by Windsor Denim! They feature a flattering high-rise waist with a lace-up placket, a form-hugging fit, and an edgy raw cut-off hem on premium denim fabric with minimal stretch. Complete the look in a cool graphic top for a concert!

    Fit & Features

    • High-rise waist
    • Lace-up placket
    • Form-hugging fit
    • Raw cut-off hem
    • Four-pocket styling, belt loop accents
    • Premium denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0328

    Category Name: Vacation Looks

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dainty Chic Shine Layered Star Charm Necklace

    Show off a dainty chic shine with this layered star charm necklace. It features a shorter layer with a beaded chain design and a longer layer with a center star charm with a gemstone accent. Style with your fave hoop earrings.

    Fit & Features

    • Premium silver-dipped or gold-dipped necklace
    • Two-row layered design
    • Shorter layer, beaded chain design
    • Longer layer, center star charm, gemstone accent
    • Lobster clasp closure

    Style Number/Barcode: 07002-1513

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Slay Ribbed Knit Midi Dress

    Showcase an everyday slay in this curve-hugging midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a double strap design, a midi-length hem with a bodycon silhouette, and a thigh-high side slit for a sultry accent. The ribbed knit fabric offers plenty of stretch. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, double strap design, tie closure
    • Midi-length hem, bodycon silhouette
    • High side slit
    • Ribbed knit fabric, lining at the bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4770

    Category Name: Vacation Looks

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Sunshine Linen Tie-Back Midi Dress

    For the sun-soaked days ahead, this linen midi dress will make a cute companion! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back closure, and a flowy ruffled hem. Style with trendy sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Tie-back closure
    • Flowy ruffled midi hem
    • Airy linen fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5012

    Category Name: Vacation Looks

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • She's A Doll Sweetheart Skater Dress

    You'll be looking like a total doll in this poplin skater mini dress for graduation and family parties! The dress features adorable puff short sleeves, a sweetheart neckline, an empire waist seam, and a flattering fit and flare short-length silhouette. Complete the look in eye-catching lace-up heels.

    Fit & Features

    • Puff short sleeves, sweetheart neckline
    • Back zipper and hook-eye closure
    • Empire waist seam
    • Fit and flare, skater silhouette
    • Short-length hem
    • Poplin cotton-blend fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2324

    Category Name: Vacation Looks

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Glam Rhinestone Oversized Sunglasses

    Level up your looks with these embellished sunglasses that bring the summer glam! They feature an oversized flat top design with two rows of mini rhinestone embellishments and reflective lenses. Complete your accessories with sleek hoop earrings.

    Fit & Features

    • Oversized flat top design
    • Two rows of mini rhinestones
    • Reflective lenses
    • Plastic frame

    Style Number/Barcode: 07008-1011

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pleated Princess Bow Back Skater Dress

    Look and feel like a princess in this skater dress for cocktail wedding showers or graduation parties! It features a sleeveless square neck, adjustable spaghetti straps, a pleated bodice with a pretty bow on the back, and a fit-and-flare short silhouette. Complete the look in stiletto mules and a clutch.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Pleated bodice, back bow, zipper closure
    • Skater, fit and flare silhouette
    • Short-length hem
    • Cotton-blend fabric, smooth woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2333

    Category Name: Vacation Looks

    Price: $5.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Trendsetter Strappy Platform Sandals

    Show up this season with a trendy summer style in these sleek and strappy platform sandals. They feature a round toe, a dual adjustable strap design with buckle and stud details and a patent faux leather sheen, an open back for easy on-and-off styling, and an edgy platform lug sole. Pair these sandals with a graphic tee and distressed denim shorts.

    Fit & Features

    • Round toe
    • Dual adjustable strap design
    • Buckle and stud details, patent faux leather sheen
    • Open back, slip-on design
    • Platform lug sole
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07404-1146

    Category Name: Vacation Looks

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Desert Vibes Turquoise Stone Cowboy Hat

    Elevate your desert weekend getaway looks with this chic cowboy hat. It features a structured top, a wide, curved, up-turned brim, and a sleek thin faux leather band with detailed metal accents with turquoise stone embellishments. Style with a corset top and denim shorts.

    Fit & Features

    • Structured top
    • Wide, curved, up-turned brim
    • Thin faux leather band
    • Detailed metal accents
    • Turquoise stone embellishments

    Style Number/Barcode: 07302-1470

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • '90s Babe Butterfly Hair Clip Pack

    Throw it back and get the cutest '90s babe look with this trendy butterfly hair clip pack. The set features six pairs of small butterfly clips in assorted multi-colored hues. Style with hoop earrings.

    Fit & Features

    • Small butterfly hair clips
    • Six pairs
    • Assorted multi-colored hues

    Style Number/Barcode: 07006-0401

    Category Name: Vacation Looks

    Price: $3.97 $8.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirtatious Mood Ruffled Knit Romper

    Style up this flirty ruffled knit romper for your summer weekend plans! It features an off-the-shoulder neckline with a dainty ruffled trim, short puff sleeves, ruching at the bust, a stretchy smocked waist, and an adorable tiered ruffled design with a short skirt layered over flowy shorts. Complete the look with beaded earrings.

    Fit & Features

    • Off-the-shoulder neckline, ruffled hem
    • Short puff sleeves, cinched hems
    • Ruched bust
    • Stretchy smocked waist
    • Tiered ruffled design, short skirt overlay, flowy shorts
    • Crepe fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06503-1059

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shorebird Crochet Woven Kimono

    Chill along the shore looking so trendy in this crochet woven kimono featuring flowy, long sleeves with cuffs and a sheer longline design. Complete the look in a crop top and denim shorts.

    Fit & Features

    • Flowy long sleeves with cuffs
    • Open-front
    • Sheer longline design
    • Crochet woven fabric

    Style Number/Barcode: 06202-0363

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's All Business V-Neck Mini Dress

    Business and babe vibes are what this woven mini dress is all about! It features a sleeveless V-neckline, wide shoulder straps, a wrap-style bust with sultry cutouts, and a form-hugging silhouette. Style with stiletto pumps and a blazer to complete the look for a cocktail event!

    Fit & Features

    • Sleeveless V-neckline, wide shoulder straps
    • Back zipper and hook-eye closure
    • Wrap-style bust, cutouts
    • Form-hugging silhouette
    • Mini-length hem
    • Woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2438

    Category Name: Vacation Looks

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Smooth Silhouette Slit Midi Skirt

    Create the perfect basics closet by adding this smooth knit midi skirt to your lineup! It features a sleek and flattering high-rise waist, a bodycon fit, and a sultry side high slit along the midi-length hem. The double-lined stretchy knit fabric offers a seamless design and has an ultra-butterfly feel. Style with the matching top for a complete look!

    Shop Matching Top: Smooth Silhouette Crop Tube Top

    Fit & Features

    • High-rise waist
    • Bodycon fit
    • High side slit
    • Midi-length hem
    • Double-lined, butterfly soft knit fabric
    • Seamless design
    • Runs true to size

    Style Number/Barcode: 06501-0849

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Naturally Cute Strappy Platform Wedges

    Naturally, summer calls for cute styles like this platform wedge perfect for hanging poolside or a beach day! It features a square toe, a strappy design, a platform sole, slightly cushioned footbed, and an ankle strap with buckle closure. Complete the look with a breezy kimono.

    Fit & Features

    • Square toe
    • Strappy design
    • Platform style
    • Ankle strap with buckle closure
    • Slightly cushioned footbed
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07406-0318

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale