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.

  • Right On Cue Crepe Skort Romper

    Step out in this crepe skort romper and watch the heads turn! It features a sleeveless, v-neck, spaghetti straps, a high waist seam, and an envelope front design with shorts underneath. Complete the look in bold earrings for a daytime outing.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • High waist seam
    • Envelope front design
    • Cheeky shorts
    • Crepe-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06503-1001

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Jazz Night High Rise Pants

    Enter the room of the rhythm and blues! All eyes on you in these high-rise pants featuring a wide-leg silhouette, pull-on/off styling on pleated-lined fabric. Complete the look in the matching top.

    Shop Matching Top: Jazz Night Twist Front Crop Top

    Fit & Features

    • High-rise waistband
    • Wide-leg silhouette
    • Pull-on/off styling
    • Pleated-lined fabric
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06502-1282

    Category Name: Vacation Looks

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Spot Sweater Knit Bustier

    Stay sweet for the summer in your new fave bustier! It features a strapless, sweetheart neckline with wire underbust support, built-in padded cups, seam detailing along the bodice, and a fitted hem. Complete the look in skinny jeans for a dinner date. 

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Strapless, sweetheart neckline
    • Wire underbust support
    • Built-in padded cups
    • Seam detailing along the bodice
    • Fitted hem
    • Sweater-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1378

    Category Name: Vacation Looks

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Street Riders Graphic Short Dress

    You're not the average Jane...show your edgy side in this graphic short dress for a night of riding! It features a sleeveless, one-shoulder neckline with chain straps, a cutout accent, and a front graphic script that reads, " The Street Riders/Motorcycle Company", a bodycon silhouette, and a short-length hem. Complete the look in combat boots.

    Fit & Features

    • One-shoulder neckline, chain straps, cutout accent
    • A front graphic script that reads, " The Street Riders/Motorcycle Company"
    • Bodycon silhouette
    • Short-length hem
    • Cotton knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1314

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Boho Stunner Printed Scarf Top

    Show off your stunning boho-chic style in this printed scarf top. It features a sleeveless cowl neckline, halter spaghetti straps, a bold open-back with a tie-back design, and a cropped angled front hem. The smooth woven fabric features an all-over bohemian-inspired multi-print pattern. Pair this top with a faux suede mini skirt and mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Open-back, tie-back design
    • Cropped angled front hem
    • Multi-print pattern
    • Lined woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06003-1904

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Moment Claw Clip Set

    Have a totally trendy moment with these adorable claw clips! The set features three metal hair clips with varying designs to switch up your looks. Style with simple stud earrings and a charm necklace.

    Fit & Features

    • Set of three metal claw clips
    • Different designs

    Style Number/Barcode: 07006-0335

    Category Name: Vacation Looks

    Price: $5.97 $13.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Hit Of The Night Halter Crop Top

    You'll be the hit of the night in this sexy crop top featuring a trendy, off-the-shoulder, halter neckline, twist front design, and attached long sleeves. Complete the look in sleek faux leather leggings.

    Fit & Features

    • Off-the-shoulder 
    • Halter neckline, tie closure
    • Twist front design
    • Attached long sleeves
    • Cropped hem
    • Knit lined fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06001-4326

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Staple Crepe Suspender Skirt

    Your new elevated sweet staple! Showcase your unique style in this crepe skirt with attached suspenders, a high-rise, bodycon silhouette, and a front slit accent. Complete the look in a puff sleeve crop top and heels.

    Fit & Features

    • Attached suspenders
    • High-rise
    • Bodycon silhouette
    • Front slit accent
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06501-0684

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Amanda High Rise Boyfriend Jeans By Windsor Denim

    Ultra-flattering and edgy, keep your look trendy in the Amanda boyfriend jeans by Windsor Denim! They feature a classic high-rise waist, front distressed accents, and a cuffed hem on medium wash denim with no stretch. Complete the look in strappy mules.

    Fit & Features

    • High-rise waist
    • Front distressed accents
    • Boyfriend silhouette
    • Cuffed hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, no stretch, fits true to size

    Style Number/Barcode: 06602-0337

    Category Name: Vacation Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pit Stop Acid Wash Denim Jacket

    The perfect denim trucker jacket for one stylish pit-stop! It features an oversized silhouette with long sleeves, button cuffs, a collared neckline, front flap pockets, a button-down front, and belt loop waist accents on acid wash denim fabric. Complete the look in a basic bodysuit and shorts.

    Fit & Features

    • Long sleeves, button cuffs, collared neckline
    • Front flap pockets
    • Button-down front
    • Belt loop waist accents
    • Oversized silhouette
    • Acid wash denim fabric
    • Fits true to szie

    Style Number/Barcode: 06203-0477

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • That's A Wrap Crew Neck Crop Tee

    Your outfit of the day will slay in this crew neck tee featuring short sleeves and a wrap-tie cropped hem on stretchy, rib-knit fabric. Complete your trendy look in mid-rise jeans and sandals.

    Fit & Features

    • Short fitted sleeves
    • Crew neck
    • Wrap-tie cropped hem
    • Stretchy rib-knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1371

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Free Bird Mesh Lace-Up Paisley Top

    This paisley mesh top calls for a sun-soaked adventure! It features long sleeves, a plunge neckline, front lace-up closure, and a cropped hem on mesh-lined fabric. Complete your boho look in flared jeans.

    Fit & Features

    • Long sleeves
    •  Plunge neckline
    • Front lace-up closure
    • Cropped hem
    • Paisley mesh-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4338

    Category Name: Vacation Looks

    Price: $29.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Harper Mid Rise Skinny Jeans By Windsor Denim

    Forever-flattering and your new favorite! The Harper skinny jeans by Windsor denim feature a classic, mid-rise waist, distressed accents, and trendy knee slits on curve-hugging, medium wash denim fabric with a vintage-inspired color fade effect. Complete the look in a sleeveless bodysuit and sandals.

    Fit & Features

    • Mid-rise waist
    • Distressed accents, knee slits
    • Skinny-leg design
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim, color fade effect
    • Fits true to size

    Style Number/Barcode: 06602-0321

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Step Up Abstract Print Cutout Mini Dress

    Step up your night-out vibe in this bold abstract print mini dress designed with a plunging halter neck, open back, and sultry waist cutouts. The bodycon fit will flaunt your gorgeous curves.

    Fit & Features

    • Sheer mesh fabric with brushed knit lining, high stretch
    • Abstract print
    • Sleeveless plunging V-neckline, tie-back halter straps
    • Textured metal accent, side cutouts, waist keyhole cutout
    • Open back, tie-back spaghetti straps, lower back ruching
    • Mini-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-000104

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Speechless Satin Tie-Front Top

    Leave your date speechless in this silky satin crop top featuring eye-catching, bell sleeves, a v-neckline, and tie-front closure. Complete the look in chic hair clip and jeans.

    Fit & Features

    • Bell sleeves
    • V-neckline
    • Tie-front closure
    • Cropped hem
    • Silky satin woven fabric
    • Fits true to size

    Style Number/Barcode: 06204-1455

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Moto Graphic Tank Crop Top

    Enter the legendary racers club in this edgy tank crop top featuring a sleeveless, scoop neck, tank-style straps, front graphic detailing with "American Motorcycle" script, and contrast-stitched seams along the curved hem. Complete the look in cool denim shorts and combat boots.

    Fit & Features

    • Sleeveless, scoop neck, tank-style straps
    • Front graphic detail
    • "American Motorcycle" script
    • Contrast-stitched seams
    • Curved, crop hem
    • Cotton knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1293

    Category Name: Vacation Looks

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Hot And Cold Shoulder Strappy Top

    Bare your shoulders for a night on the town in this knit crop top featuring a sleek, cold shoulder neck with a strappy design, long sleeves, and a fitted crop hem. Complete the look in fab new bottoms and heels. 

    Fit & Features

    • Cold shoulder neck
    • Strappy design
    • Long sleeves
    • Fitted crop hem
    • Knit fabric
    • Fits true to size

    Style Number/Barcode: 06001-4405

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Butterflies Rhine Earrings

    You might feel all the butterflies for these whimsical earrings! They feature a linear design with butterfly charms and a post-back closure. Complete the look in glam stiletto heels.

    Fit & Features

    • Rhinestone butterfly charms
    • Post-back closure
    • Linear design

     

    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-1315

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Nothing But Edge Coated Romper

    Get ready to show off your curves in this edgy coated romper featuring a sleek, sleeveless square neck, spaghetti straps, high waist seam, and flirty waist cutouts leading to the short-length hem. Complete the look in statement earrings for a night on the town.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Back zipper closure
    • High waist seam, cutouts
    • Form-fitting silhouette
    • Short-length hem
    • Coated faux leather fabric
    • Fits true to size

    Style Number/Barcode: 06403-0236

    Category Name: Vacation Looks

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Playing Favorites Lace-Up Tank Top

    Somebody's playing favorites! You'll fall for this floral tank top featuring a sleeveless, scoop neck, tank-style straps, princess seam detail, and a trendy front lace-up with tie closure along the fitted, crop hem. Complete the look in shorts and sandals for a daytime event.

    Fit & Features

    • Sleeveless, scoop neck, tank-style straps
    • Front lace-up, tie closure, princess seam detail
    • Fitted crop hem
    • Ditsy floral print
    • Ribbed-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4285

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Girl On The Run Plaid Crop Blazer

    Arrive in style in this plaid crop blazer featuring long sleeves, shoulder pads for a structured fit, lapel collar neckline, and three front hook-eye closures, crafted on woven lined fabric. Complete the look in sleek trouser pants and heels.

    Fit & Features

    • Long sleeves
    • Lapel collar neckline
    • Three front hook-eye closures
    • Cropped hem
    • Buffalo plaid pattern
    • Woven lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06204-1461

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make A Wish Starburst Earrings

    Make a wish and these starburst earrings will be yours! They feature a linear silhouette, rhinestone insets, and a post-back closure. Complete the look in a matching set for a cute daytime outing.

    Fit & Features

    • Linear silhouette
    • Starbursts design
    • Rhinestone insets
    • Post-back closure 

     

    Earrings are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07001-1305

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Remy High Rise Distressed Shorts By Windsor Denim

    Your new favorite go-to denim shorts that hug just right! The Remy shorts by Windsor Denim feature a flattering, high-rise waist, minimal distressed accents, cool color fading, and a cut-off hem on dark wash denim fabric. Complete the look in a flirty tie-front top and sandals.

    Fit & Features

    • High-rise waist
    • Minimal distressed accents
    • Cut-off hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Color fading, dark wash denim, minimal stretch
    • Fits true to size

    Style Number/Barcode: 06603-0281

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Leopard Instinct Slit Midi Skirt

    Unleash your fierce-feline side looking so femme in this leopard midi skirt featuring a sleek, high-rise waist, slim fit silhouette, and a sultry front slit accent perfect for showcasing chic mules.

    Fit & Features

    • High-rise waist
    • Slim-fit silhouette
    • Front slit accent
    • Midi-length hem
    • Leopard print
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06501-0671

    Category Name: Vacation Looks

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance