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.

  • Coffee Break Smock Tie Waist Joggers

    The perfect woven joggers to throw on and get your coffee break on! They feature a high-rise smocked waist with a tie closure, front and back pockets, and a loose-fit leg with smocked cuffs. Complete the look in a trendy denim jacket.

    Fit & Features

    • High-rise smocked waist, tie closure
    • Front and back pockets
    • Loose-fit leg
    • Smocked cuffs
    • Woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06302-0639

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Spots Leopard Satin Scarf Top

    Spotted in the wild! This fierce leopard satin scarf top features adjustable spaghetti straps, a square neckline, and a cropped hem with tie-back closure. Complete the look in boyfriend jeans and heels.

    Fit & Features

    • Adjustable spaghetti straps
    • Square neckline
    • Leopard print
    • Cropped hem, tie-back closure
    • Satin fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1613

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • In The Bag High Rise Denim Shorts

    You've got style in the bag! These cute high-rise denim shorts feature a paper bag elasticized waist, trendy distressed accents, and a cuffed hem on vintage-inspired medium wash denim. Complete the look in a basic tee and sneakers.

    Fit & Features

    • High-rise paper bag elasticized waist
    • Distressed accents, cuffed hem
    • Front single button and hidden zipper closure
    • Four-pocket styling, belt loop accents
    • Vintage-inspired medium wash denim
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06603-0272

    Category Name: Vacation Looks

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Disco Era Rhinestone Trim Sunglasses

    Create a groovy vibe in these round sunglasses featuring rhinestone trim, gradient colored lens, rubber nose supports, and a sleek metal frame. Complete the look in a chic mesh dress for the festival season.

    Fit & Features

    • Round sleek metal frame
    • Rhinestone trim
    • Gradient colored lens
    • Rubber nose supports
    • 100% UV protection

    Style Number/Barcode: 07008-0943

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring The Heat Tropical Mesh Duster

    Bring the heat to your vacay look in this tropical mesh duster featuring long sleeves and an open-front design. Complete the look in the matching top and bottoms. 

    Shop The Matching Top: Bring The Heat Printed Tube Top

    Shop The Matching Bottoms: Bring The Heat Printed Midi Skirt

    Fit & Features

    • Long sleeves
    • Open-front
    • Tropical print
    • Sheer mesh fabric
    • Longline hem
    • Fits true to size

    Style Number/Barcode: 06202-0274

    Category Name: Vacation Looks

    Price: $23.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • High Priority Mock Neck Crop Top

    Every fashionista needs a staple like this mock neck crop top to create all sorts of looks. It features a sleeveless bodice on rib-knit fabric with a moderate stretch. Perfect for styling with a boyfriend blazer and jeans.

    Fit & Features

    • Sleeveless, mock neck
    • Cropped hem
    • Rib-knit 
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06002-1240

    Category Name: Vacation Looks

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romance In Bloom Floral Ruffle Slit Midi Dress

    She’s giving romance with a side of sass. This strapless midi stuns with flirty ruffle trim and a high front slit—aka your new fave for shower celebrations and dressy brunches! 

    Fit & Features

    • Floral print, airy woven fabric, stretchy knit lining
    • Strapless sweetheart neckline, twist bust accent
    • Hidden side zipper and hook-eye closure
    • Curve-hugging silhouette
    • High front ruffled trim slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000651

    Category Name: Vacation Looks

    Price: $52.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: S, M, L

  • Bloom Mood Floral Tie-Front Top

    Bloom with a floral top that brings the charm! The top features a pretty floral print, a plunging V-neckline with tie-front accent, long blousant sleeves, and a cropped hem. The top is composed of a semi-sheer lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with high waist jeans and mules for the perfect day date outfit.

    Fit & Features

    • Plunging V-neckline
    • Tie-front accent
    • Floral print
    • Long blousant sleeves
    • Cropped hem 
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 06204-1337

    Category Name: Vacation Looks

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bohemian Chic Paisley Tie Front Top

    Channel a bohemian chic vibe with a tie front top that brings on those lowkey vibes! The top features a bohemian paisley, a plunging V-neckline with a tie-front accent, long sleeves with elastic cuff, and a cropped hem. The top is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with a wrap skirt and mules. 

    Fit & Features

    • Paisley print
    • V-neckline
    • Tie-front hem 
    • Cropped hem
    • Lightweight woven fabric 
    • Minimal stretch
    • Runs true to size

    Style Number/Barcode: 06204-1231

    Category Name: Vacation Looks

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Retreat Chiffon Sweetheart Midi Dress

    Ready for a floral retreat? Feel the sunshine on your shoulders in this floral chiffon midi dress featuring dainty spaghetti straps, a sweetheart neckline with a bust tie, a fitted bodice, and a side slit accent. Complete the look in simple heels.

    Fit & Features

    • Sleeveless sweetheart neckline, bust tie accent
    • Spaghetti straps
    • Fitted bodice, back zipper, hook and eye closure
    • Midi-length hem, side slit
    • Ditsy floral pattern
    • Sheer chiffon fabric, knit lining
    • A-line silhouette, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4356

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • More Bling Please Round Sunglasses

    The more bling, the better! Showcase a festival-inspired 'fit with these fab sunglasses. They feature round tinted lenses with a rhinestone embellished outline and a thin metal frame. Style these shades with rhinestone fringe earrings.

    Fit & Features

    • Round tinted lenses
    • Rhinestone embellished outline
    • Thin metal frame
    • 100% UV protection

    Style Number/Barcode: 07008-0934

    Category Name: Vacation Looks

    Price: $5.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cross My Mind Comfort Slide Sandals

    If these sandals have crossed your mind, it's definitely a sign that you want them! They feature an almond toe, criss-cross straps, and a comfortable footbed. Complete the look in a casual jumpsuit for a beach brunch.

    Fit & Features

    • Almond toe
    • Criss-cross straps
    • Comfortable footbed
    • Slide-on/off styling 
    • PU material
    • Runs true to size

    Style Number/Barcode: 07404-1027

    Category Name: Vacation Looks

    Price: $12.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Crush Puff Sleeve Crop Top

    We're totally crushing on this adorable crop top, perfect for creating an effortless look! It features a deep V-neckline with a tie-front design, long puff sleeves with tapered, flared-out hems, and a majorly cropped fit. Style this top with high waist denim and cute sunnies.

    Fit & Features

    • V-neckline
    • Tie-front design
    • Long puff sleeves, tapered, flared-out hems
    • Elasticized hems
    • Cropped, form-hugging fit
    • Lightweight woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1646

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunny Days Floral Crop Top

    Bring the good vibes with this adorable puff sleeve crop top! It features a V-neckline, a tie-front design, a cropped fit, and an all-over dainty floral print. Style this top with cut-off denim shorts and sandals for the cutest spring look.

    Fit & Features

    • Short puff sleeves, elasticized hems
    • V-neckline
    • Tie-front
    • Cropped
    • Floral print
    • Lightweight woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1197

    Category Name: Vacation Looks

    Price: $18.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect Cut Snake Bodysuit

    This knit bodysuit has perfect cuts in all the right places! Bring the heat in this snake print bodysuit featuring a sleeveless, one-shoulder strap design with hoop inset and a sultry cutout bodice. Complete the look in boyfriend jeans for happy hour.

    Fit & Features

    • Sleeveless, one-shoulder strap, hoop inset
    • Cutout bodice
    • Snake print 
    • Thong bottom, dual snap-button closures
    • Fits true to size

    Style Number/Barcode: 06001-3981

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Edgy Links Wrap Platform Wedges

    Edgy and sultry, these platform wedges are perfect for warm nights! They feature an almond toe, chain-link toe strap, a wrap-around ankle with buckle closure, and faux suede material. Complete the look in a chic jumpsuit.

    Fit & Features

    • Almond toe
    • Chain-link toe strap
    • Wrap-around ankle, buckle closure
    • Platform sole
    • Faux suede material

    Style Number/Barcode: 07406-0288

    Category Name: Vacation Looks

    Price: $12.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Day Trip Twist Cutout Linen Romper

    Take a day trip looking so cute in this linen romper! It features a sleeveless, v-neck, adjustable spaghetti straps, a twisted cutout bodice on high-waist flowy shorts, and a partial open-back design with tie-closure. Complete the look in trendy wedges.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Twisted cutout bodice
    • Partial open-back, tie-closure
    • Flowy high-waist shorts
    • Linen fabric
    • Fits true to size

    Style Number/Barcode: 06303-0190

    Category Name: Vacation Looks

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Pick Me Floral Surplice Top

    This floral surplice top is the perfect pick for your closet! It features peasant long sleeves, a plunge V-neckline, and a surplice wrap bodice on a cropped hem. Complete the look in sleek faux leather pants.

    Fit & Features

    • Peasant long sleeves
    • Plunge V-neckline
    • Surplice wrap bodice
    • Cropped hem
    • Floral mesh partially lined fabric
    • Runs true to size

    Style Number/Barcode: 06001-3989

    Category Name: Vacation Looks

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

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

    Fits like a dream and goes with everything! Say hello to the Harper Mid-Rise Skinny Jeans By Windsor Denim. They feature trendy distressed accents on the skinny-leg design and an ankle grazer hem on vintage-inspired medium wash denim fabric. Complete the look in a cute sweater top and sneakers for a casual hang. 

    Fit & Features

    • Mid-rise waist
    • Distressed accents
    • Skinny-leg design, ankle grazer hem
    • Classic five-pocket styling, belt loop accents
    • Front button and hidden zipper closure
    • Vintage medium wash denim fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06602-0322

    Category Name: Vacation Looks

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Remy High-Rise Destructed Cut-Off Shorts

    The Remy destructed cut-off shorts will be your fave pair of the season! They feature a high-rise waist, trendy distressed detailing down the front, and a frayed, cut-off hem. The denim fabric offers a minimal stretch. Complete your casual everyday look with a cropped graphic tee and sneakers.

    Fit & Features

    • High-rise waist
    • Destructed detailing, frayed cut-off hem
    • Form-hugging fit
    • Five-pocket and belt loop design
    • Front button-down closure
    • Denim fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06603-0297

    Category Name: Vacation Looks

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vintage Mood Activated Retro Sunglasses

    These retro-inspired oval sunglasses give your fit an instant upgrade—perfect for rooftop brunches, low-key flexes, and celeb-off-duty moments.

    Fit & Features

    • Oval lens shape with slim metal frame
    • Nose support pads
    • 100% UV protection
    • Retro-inspired silhouette

    Style Number/Barcode: 07008-000012

    Category Name: Vacation Looks

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Grade A Linen Bustier

    If this bustier could get graded it'd receive an A. It features a sleeveless, boat neck, adjustable spaghetti straps, a cropped hem, hook-eye back closures, and flexible boning to provide structure. Complete the look in high-rise jeans for wine tasting.

    Fit & Features

    • Sleeveless boat neck
    • Adjustable spaghetti straps
    • Flexible boning
    • Cropped hem
    • Back hook-eye closures
    • Lined linen fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 06003-1743

    Category Name: Vacation Looks

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Twist Knot Ribbed Bikini Top

    Chill off in this cute bikini top that will have you ready for fun in the sun! The bikini top features a cute twist front accent at the center, triangle cups with removable padding, and adjustable tank shoulder straps. Complete look with the matching bikini bottoms. 

    Shop Matching Bikini Bottoms: High Waist Ribbed Bikini Bottoms

    Fit & Features

    • Twist-front accent 
    • Removable padding
    • Triangle cups
    • Adjustable tank straps
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 07104-0677

    Category Name: Vacation Looks

    Price: $8.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Swirl Bikini Top

    Keep it sassy in a bikini top that keeps your look on-trend! The bikini top features a fab swirl print, triangle cups with removable padding, halter ties for an adjustable fit, and back ties. Complete look with the matching bikini bottoms and sarong. 

    Shop Matching Bikini Bottoms: Sassy Swirl Hipster Bikini Bottoms

    Shop Matching Sarong: Sassy Swirl Swim Sarong

    Fit & Features

    • Swirl pattern 
    • Triangle cups
    • Removable padding
    • Halter neck ties
    • Back ties
    • Runs true to size 

    Style Number/Barcode: 07104-0679

    Category Name: Vacation Looks

    Price: $8.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale