Vacation Looks

Loading...

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.

  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Versatile Basic Rib Knit Crop Top

    Your new favorite basic to create all sorts of showstopping outfits! This rib knit crop top features long sleeves, a scoop neck, and a fitted hem. Complete the look in a plaid skirt, jacket, and booties for the perf autumn vibe!

    Fit & Features

    • Long fitted sleeves
    • Scoop neckline
    • Fitted cropped hem
    • Soft and stretchy
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1438

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Warm Embrace Cable Knit Sweater

    Cozy up on chilly autumn days in this cable knit sweater featuring the perfect oversized fit, long sleeves with ribbed cuffs, a mock neckline with a trendy cutout, and a relaxed hem. Complete the look in leggings and cute suede boots.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Long sleeves, ribbed cuffs
    • Mock neckline with cutout
    • Oversized silhouette
    • Relaxed fit hem
    • Cable knit design
    • Fits true to size

    Style Number/Barcode: 06005-1452

    Category Name: Vacation Looks

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Always Chic Over-The-Knee Slouch Boots

    Your look will always be chic in these bold over-the-knee boots! They feature a slouched design, a pointed toe, a sleek stiletto heel, and an inner zipper closure. Pair with a corset top and a faux leather skirt and strut in style!

    Fit & Features

    • Over-the-knee fit
    • Slouched design
    • Pointed toe
    • Stiletto heel
    • Zipper closure
    • Faux leather material, smooth lining
    • Runs true to size

    Style Number/Barcode: 07402-0830

    Category Name: Vacation Looks

    Price: $30.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fabulous Diva Leopard Print Faux Fur Coat

    Layer on this ultra-soft faux fur coat to showcase fabulous diva energy! The coat features a lapel collar, long sleeves, lined side pockets, a relaxed silhouette, and an all-over trendy leopard print pattern. The faux fur fabric includes a knit lining. Style with knee-high boots.

    Fit & Features

    • Lapel collar
    • Long sleeves
    • Lined side pockets
    • Relaxed fit
    • Leopard print
    • Faux fur fabric, knit lining with minimal stretch
    • Runs true to size

    Style Number/Barcode: 06201-0322

    Category Name: Vacation Looks

    Price: $21.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stacked On Style Lace-Up Boots

    Stack on the style with boots that dare to go bold! The faux suede boots feature an over-the-knee shaft length, a sexy bungee strap lace-up back, an inner zipper closure, a pointed toe, and a sleek stiletto heel. Complete the look with a sweater and mini skirt for a dinner date!

    Fit & Features

    • Over-the-knee shaft length
    • Lace-up bungee strap back 
    • Inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux suede material 
    • Runs true to size

    Style Number/Barcode: 07402-0825

    Category Name: Vacation Looks

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chill Tale Corduroy Faux Sherpa Shacket

    This tale is as chill as time! The corduroy shacket offers a cozy and cute look to bundle up in this season. It features long sleeves, button cuffs, a hooded neckline, four-pocket styling, a button-down front, and a longline hem with faux sherpa lining. Complete the look in knee-high boots.

    Fit & Features

    • Long sleeves, button cuffs
    • Hooded neckline
    • Four-pocket styling
    • Button-down front
    • Longline hem
    • Corduroy fabric, faux sherpa lining, no stretch
    • Fits true to size

    Style Number/Barcode: 06201-0307

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Knit Distress Crop Sweater

    The perfect knit crop sweater to level up your autumn closet! The crew neck sweater features long sleeves and a hem with distressed accents on a purl knit fabric. Complete your trendy look in high-rise jeans and booties for everyday styling!

    Fit & Features

    • Long sleeves and hem with distressed accents
    • Crew neck
    • Cropped length
    • Purl knit design
    • Fits true to size

    Style Number/Barcode: 06005-1548

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Femme Edge Platform Lug Booties

    Play up your edgy female energy in these faux leather booties featuring a trendy utility design, a round toe, block heel, chunky platform lug sole, knit side panels, and inner zipper closure on an ankle-length shaft. Complete the look in a cool moto jacket!

    Fit & Features

    • Round toe
    • Block heel
    • Chunky platform lug sole
    • Side knit panels and inner zipper closure
    • Ankle-length shaft
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1559

    Category Name: Vacation Looks

    Price: $12.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cold Babe Plaid Blanket Scarf

    You can still be a babe and brace for the cold thanks to this cozy plaid blanket scarf! It features a trendy fringe edge design on cozy and soft fabric. Complete the look in a trendy jacket for a coffee run.

    Fit & Features

    • Plaid pattern
    • Fringe edge design
    • Soft and cozy fabric

    Style Number/Barcode: 07305-0431

    Category Name: Vacation Looks

    Price: $3.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best Of Friends Color Block Sweater

    You and this cozy sweater will be the best of friends! The sweater top features color block long sleeves, a crew neck, a ribbed-knit design, and a relaxed fit hem. Complete the look in skinny jeans.

    Fit & Features

    • Color block long sleeves
    • Crew neck
    • Relaxed silhouette
    • Ribbed-knit design
    • Comfortable and soft fabric
    • Fits true to size

    Style Number/Barcode: 06005-1521

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The OG Rock Babe Slash Graphic Tee

    Flaunt your original status as a rock babe in this edgy graphic tee featuring short sleeves, a crew neck with a V-cut notch, a slashed hem, and a front script that reads, "The Original Rock N Roll". Complete the look in sleek faux leather shorts for a concert!

    Fit & Features

    • Short sleeves
    • Crew neck
    • V-cut notch
    • Slashed crop hem
    • Front script that reads, "The Original Rock N Roll"
    • Graphic detailing
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1428

    Category Name: Vacation Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Jay High-Rise Wide Leg Jeans By Windsor Denim

    Easy, breezy, and effortlessly cool slip into the Jay jeans by Windsor denim designed to showcase your edgy-cute style! They feature a flattering high-rise waist, front distressed accents, and knee rips along the wide-leg silhouette. The jeans are crafted from a medium wash with vintage-inspired color fading for the perfect worn-in fit and feel. Complete the look in sleek pointed-toe booties.

    Fit & Features

    • High-rise waist
    • Front distressed accents, knee rips
    • Wide-leg silhouette
    • Hidden front five-button fly
    • Five-pocket styling, belt loop accents
    • Medium wash denim, color fade effect
    • Runs true to size

    Style Number/Barcode: 06602-0380

    Category Name: Vacation Looks

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Look Back At Me Cable Knit Top

    Watch head-turn as you walk by in this fab cable knit sweater top featuring a sleeveless mock neck, a flirty open-back design, and a cropped hem. Pair with skinny jeans and booties for a fall festival!

    Fit & Features

    • Sleeveless mock neck
    • Open-back design
    • Cropped hem
    • Cable knit sweater fabric
    • Soft and comfortable
    • Fits true to size

    Style Number/Barcode: 06005-1673

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry Bloom Floral Mesh Tube Top

    Serve a sultry vibe in this blooming floral printed mesh tube top! Designed with ruched side seams to show off your curves, style with the matching maxi skirt for a gorgeous look.

    Shop Matching Bottoms: Sultry Bloom Floral Mesh Maxi Skirt

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Strapless straight neckline, no-slip strip
    • Ruched side seams
    • Mid-length hem
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06001-5714

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Date Vibes Satin Cropped Blouse

    Get a dreamy-chic look for date night with this sleek satin cropped blouse! It features a deep V-neckline with a wrap-front, long peasant sleeves with smocked hems, a lace-up back design, and a cropped, form-hugging fit. The lightweight woven satin fabric has no stretch. Style with faux leather pants and heels.

    Fit & Features

    • V-neckline, wrap-front
    • Long peasant sleeves, tapered smocked hems
    • Lace-up back design, tie closure
    • Cropped hem, form-hugging fit
    • Woven satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1831

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Press Pause Faux Leather Corset Bodysuit

    You'll wanna press pause cause you'll be obsessed with how you slay in this faux leather corset bodysuit perfect for a night out. It features a sleeveless sweetheart neckline, adjustable and detachable spaghetti straps, ruched bust, fitted bodice, and mesh thong bottom with dual snap-button closures. Complete the look in straight-leg jeans.

    Fit & Features

    • Sleeveless sweetheart neck
    • Adjustable and detachable spaghetti straps
    • Ruched bust, back zipper closure
    • Corset-style fitted bodice
    • Mesh thong bottom, dual snap-button closure
    • Faux leather non-stretch lined fabric
    • Runs true to size

    Style Number/Barcode: 06003-1972

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Rock Babe Lace-Up Graphic Dress

    If you're a rock babe this graphic short dress is the one for you! It features short sleeves, a crew neck, a front lace-up placket, and graphic detail with a script that reads, "Rock N Roll World Tour" along the fitted hem. Complete the look in over-the-knee boots.

    Fit & Features

    • Short sleeves
    • Crew neck
    • Front lace-up placket
    • Graphic detail/ front reads, "Rock N Roll World Tour"
    • Short and fitted hem
    • Jersey knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1459

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Cropped Denim Trucker Jacket

    Layer on the casual vibes with this vintage-inspired cropped denim trucker jacket. It features a collared neckline, long sleeves, a complete button-down front, buttoned chest pockets, side pockets, and a cropped fit. Style over a basic tee with distressed jeans.

    Fit & Features

    • Collared neckline
    • Drop shoulder design, long sleeves, single button detailing
    • Button-down front
    • Buttoned chest pockets, side pockets
    • Cropped
    • Denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06203-0473

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Winter Strolls Fringe Scarf

    This ultra-soft lightweight scarf is perfect for staying cozy on outdoor strolls this winter season. It features an oblong design with fringe detailing at the hems. The faux wool material has no stretch. Style with lace-up boots.

    Fit & Features

    • Oblong design
    • Fringe detailing
    • Soft faux wool material, no stretch

    Style Number/Barcode: 07305-0425

    Category Name: Vacation Looks

    Price: $4.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wrap Me In Plaid Fringe Scarf

    Layer on this plaid scarf to brace for the cold weather ahead! It features a fringe edge design on super soft and cozy fabric. Complete the look in a cute shacket and jeans.

    Fit & Features

    • Plaid pattern
    • Fringe edge design
    • Soft and cozy fabric

    Style Number/Barcode: 07305-0432

    Category Name: Vacation Looks

    Price: $1.97 $15.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strut In Style Over-The-Knee Boots

    Strut in style in these sleek faux leather over-the-knee boots. They feature an almond-shaped toe, a tall block heel, an inner zipper closure, and a tie-back detail at the top. Pair with a bodycon dress and a moto jacket.

    Fit & Features

    • Over-the-knee design
    • Almond-shaped toe
    • Block heel
    • Partial inner zipper closure
    • Tie-back detail
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0811

    Category Name: Vacation Looks

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Safari Babe Zebra Cowl Midi Dress

    Go on safari looking like a total babe in this zebra midi dress sure to make you in charge of the animal kingdom! It features a sleeveless cowl neckline, dual spaghetti straps, and a form-hugging silhouette. Complete the look in strappy mules for brunch!

    Fit & Features

    • Sleeveless cowl neckline
    • Dual spaghetti straps
    • Form-hugging silhouette
    • Midi-length hem
    • Zebra print
    • Knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-2026

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knit Girl Cold Shoulder Sweater

    If you're a girl who loves her knit sweaters this one is for you! The cold shoulder sweater features cozy long sleeves with ribbed cuffs, a turtle neckline, a relaxed fit, and a cropped hem ribbed knit fabric. Complete the look in a skirt and knee-high boots. 

    Fit & Features

    • Long sleeves, ribbed cuffs
    • Turtle neckline
    • Cold shoulder accents
    • Relaxed fit
    • Cropped hem
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1588

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance