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.

  • Feeling Amore Tie-Back A-Line Eyelet Mini Dress

    Fall in love with this adorable eyelet mini dress perf for weekend plans. The flirty tie-back detail and ruffled A-line silhouette will get you all the compliments.

    Fit & Features

    • Eyelet knit fabric lined with stretchy knit
    • Adjustable spaghetti straps
    • Tie-back design
    • Ruffled trim
    • Short A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5434

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Life's A Breeze High Rise Shorts

    Life's a breeze under the palm trees in paradise! Create an effortless vacay vibe in this breezy short featuring a high-rise waist and flowy silhouette on palm print fabric. Complete the look in the matching top.

    Shop Matching Top: Life's A Breeze Kimono Tie-Front Top

    Fit & Features

    • High-rise waist
    • Flowy silhouette
    • Palm leaf print woven fabric
    • Runs true to size

    Style Number/Barcode: 06303-0152

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Life's A Breeze Kimono Tie-Front Top

    Life's a breeze under the palm trees in paradise! Create an effortless vacay vibe in this breezy crop top featuring 3/4 length kimono sleeves, a plunge V-neckline, and a tie-front closure on palm print fabric. Complete the look in the matching shorts.

    Shop Matching Shorts: Life's A Breeze High Rise Shorts

    Fit & Features

    • 3/4 length kimono sleeves
    • Plunge V-neckline
    • Tie-front closure
    • Cropped hem
    • Palm leaf print woven fabric
    • Runs true to size

    Style Number/Barcode: 06204-1146

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Flirt Ruched Chiffon Blouse

    Bring on the flirty vibes with a blouse that is made for romance! The blouse features a plunging V-neckline, flutter cap sleeves, a hook and eye closure, ruching at the hem, and a smocked back. The top is composed of a semi-sheer chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with mom jeans and mules. 

    Fit & Features

    • Plunging V-neckline
    • Flutter cap sleeves
    • Hook and eye front closure
    • Ruching
    • Smocked back
    • Chiffon fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06003-1805

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strappy Open-Back Knit Bodysuit

    Swap out your basic bodysuit for this sassy strappy back style! It features a sleeveless square neckline, bungee spaghetti straps, an open back with a dual bungee strap design, and a fitted silhouette with a thong bottom. Pair this bodysuit with faux leather pants and clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Open back, dual bungee strap design
    • Form-hugging fit
    • Thong bottom, dual snap button closure
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4224

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 bikini top and denim shorts.

    Fit & Features

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

    Style Number/Barcode: 06204-1320

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel The Sun Halter Sweetheart Skater Dress

    Bare your shoulders in this cute skater dress on a sunny day! Its easy, breezy design features a halter sweetheart neck, tie-back closure, a ruched bust, and a flowy silhouette and back zipper closure. Composed of seersucker woven fabric with an inner knit lining. Finish the look in lace-up sandals.

    Fit & Features

    • Sleeveless, halter sweetheart neck, tie-back closure
    • Ruched bust
    • Flowy skater silhouette
    • Above the knee length
    • Back zipper closure
    • Seersucker woven fabric, no stretch, inner knit lining
    • Runs true to size

    Style Number/Barcode: 05101-1537

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sleek Bar Charm Layer Necklace

    So sleek and so chic! This dainty layer necklace is all you need to keep your fit' on-trend. It features two-row lariat chains and three bar charms with lobster clasp closure. Complete the look in a moto jacket. 

    Fit & Features

    • Dainty chain-link layers
    • Two-row lariat chains
    • Three bar charms
    • Lobster clasp closure

    Style Number/Barcode: 07002-1005

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho Glam Statement Chain Belt

    Accessorize your trendy summer looks with this boho glam statement belt. It features a chain-link design with a rhinestone embellished square buckle to add some sparkle. Style with cutoff denim shorts.

    Fit & Features

    • Three-row chain-link design
    • Square buckle
    • Rhinestone embellishment

    Style Number/Barcode: 07301-0445

    Category Name: Vacation Looks

    Price: $2.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simplicity Is Bliss Delicate Lariat Necklace

    Keep your look simple and bliss in this delicate layer necklace featuring a five-row chain design, coin charms, and a rhinestone lariat with lobster clasp closure. Complete the look in a mock neck bodysuit for a coffee run.

    Fit & Features

    • Five-row layered design
    • Delicate chain-links
    • Coin charms, rhinestone lariat
    • Lobster clasp closure

    Style Number/Barcode: 07002-1002

    Category Name: Vacation Looks

    Price: $6.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Funky Chic Bikini Bottoms

    Funk it up under the sun! Create a retro beachy vibe in this bikini bottom featuring a high-rise waist, cheeky fit, side square ring insets, and a texture-knit lined fabric with a moderate stretch. Complete the look in the matching bikini bottoms.

    Shop The Matching Bikini Top: Funky Chic Tube Bikini Top

    Fit & Features

    • High-rise waist
    • Cheeky fit
    • Side square ring inserts
    • Textured knit-lined fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 07105-0770

    Category Name: Vacation Looks

    Price: $4.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Carefree Summer Days Woven Shorts

    These lightweight woven shorts were made for those carefree summer days! They feature a high-rise paper bag waist, a cute tie-front belt, and chic pleated detailing. Style these shorts with a basic bodysuit and slip-on sandals.

    Fit & Features

    • High-rise elasticized paper bag waist
    • Tie-front belt
    • Pleated silhouette
    • Airy gauze fabric, woven inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 06303-0165

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cali Palms Tropical Slit Maxi Skirt

    Embrace the sunshine in this palm tropical skirt perfect for your next adventure! It features a high-rise waist, form-fitting silhouette, and a sexy front slit along the maxi-length hem. Complete your vacay look in espadrille wedges.

    Fit & Features

    • High-rise elasticized waist
    • Form-fitting silhouette
    • Front slit
    • Maxi-length hem
    • Palm tropical print
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06501-0569

    Category Name: Vacation Looks

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunday's Best Floral Cutout Dress

    Create a cute look for Sunday brunch in this floral chiffon a-line dress featuring a sleeveless, v-neck, adjustable spaghetti straps, ruffled trim, cutout bodice, and a flowy, short-length hem. Complete the look in heels and a purse.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Ruffled trimming, back zipper closure
    • Cutout bodice
    • A-line silhouette
    • Flowy, short-length hem
    • Floral chiffon-lined fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1384

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Love High-Rise Lace Trim Skort

    This high-rise skort is perfect for any fun occasion! The high waist and flowy silhouette provide a flattering fit, while the uneven lace trim hem adds a touch of charm.

    Fit & Features

    • Stretchy knit fabric
    • Folded high-rise waist
    • Flowy silhouette
    • Uneven lace trim mini-length hem
    • Shorts lining
    • Runs true to size

    Style Number/Barcode: 06503-000025

    Category Name: Vacation Looks

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropic Beauty Strappy Midi Dress

    Unveil your beauty on your tropical getaway in this figure-flattering midi dress featuring a square neckline, spaghetti straps, an open strappy back design, and a bodycon silhouette on an asymmetrical midi-length hem. Complete the look in lace-up stilettos.

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • Open strappy back design
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • Tropical print fabric
    • Fits true to size

    Style Number/Barcode: 05102-4389

    Category Name: Vacation Looks

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Boho-Chic Tie-Front Top

    So effortless, this boho-chic tie-front top is the perfect lightweight summer staple. It features half-length kimono-style sleeves, a V-neckline, a tie-front design, a cropped, relaxed fit, and an all-over multi-print paisley pattern. Style with vintage-inspired jeans and cute mules.

    Fit & Features

    • Half-length kimono-style sleeves
    • V-neckline
    • Tie-front
    • Cropped
    • Multi-print paisley pattern
    • Woven gauze fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06204-1312

    Category Name: Vacation Looks

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Meli Mid-Rise Cuff Denim Shorts By Windsor Denim

    The Meli cuff denim shorts by Windsor Denim are a closet staple for this new season! They feature a mid-rise waist, trendy distressed accents, and a cuffed hem on vintage-inspired medium wash denim fabric with a color fade effect. Complete the look in a flirty tie-front top and slides.

    Fit & Features

    • Mid-rise waist
    • Distressed accents, cuffed hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Vintage medium wash denim with color fade effect
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06603-0234

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Va Va Vintage Denim Jacket

    Channel a vintage vibe with a denim jacket that is perf to layer over your fits'. The jacket features a collared neckline, a multi-button down front, two chest pockets, long sleeves, and a cropped hem with heavy distressing. Complete look with a flared pants. 

    Fit & Features

    • Collared neckline
    • Multi-button down front
    • Two chest pockets
    • Long sleeves
    • Cropped hem, distressing
    • Denim fabric 
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06203-0216

    Category Name: Vacation Looks

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lauren Double Buckle Denim Skirt by Windsor Denim

    Bring the edge with a denim skirt by Windsor denim that elevates your look! The skirt features a high-rise waist, a double buckle design with metal grommets, a side slit, and a mini-length hem. The skirt is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with a crop top and mules. 

    Fit & Features

    • High rise waist
    • Double-buckle design 
    • Front slit accent
    • Mini length hem 
    • Back zipper closure 
    • Dark wash denim, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06601-0050

    Category Name: Vacation Looks

    Price: $11.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sassy Knits Keyhole Halter Top

    So much sass on this sultry halter top! It features a sleeveless, tie-back neck closure and a front keyhole cutout, wrap-tie waist, on space-dye knit fabric with plenty of stretch. Complete the look in the matching bottoms and heels.

    Shop The Matching Bottoms: Sassy Knits Flare Pants

    Fit & Features

    • Sleeveless, halter neck with tie-back closure
    • Keyhole front cutout
    • Wrap-tie waist
    • Space dye knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06001-4121

    Category Name: Vacation Looks

    Price: $6.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sassy Knits Flare Pants

    So much sass on these flare pants! It features a high-rise waist, form-fitting silhouette, and a flared hem on space-dye knit fabric with plenty of stretch. Complete the look in the matching top and heels.

    Shop Matching Top: Sassy Knits Keyhole Halter Top

    Fit & Features

    • High-rise elasticized waist
    • Form-fitting silhouette
    • Flare hem
    • Pull-on/off styling
    • Space dye knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06502-0850

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Kaleidoscope Boho Flare Pants

    Serve major vibes in these boho flare pants featuring a high-rise waist, form-fitting silhouette, and a kaleidoscope striped print on stretchy knit fabric. Complete the look in a fringe crop top and cowgirl hat.

    Fit & Features

    • High-rise elasticized waist
    • Form-fitting silhouette
    • Kaleidoscope striped print
    • Flared hem
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06502-0861

    Category Name: Vacation Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Blend Crochet Knit Shorts

    Sun's out, legs out! These crochet-knit shorts are perfect for summer festivals and casual beach days. They feature a high-rise drawstring waist, front tie closure, and a form-fitting silhouette. Complete the look in the matching top.

    Shop Matching Top: Summer Blend Crochet Knit Top

    Fit & Features

    • High-rise drawstring waist
    • Front tie closure
    • Form-fitting silhouette
    • Crochet knit striped pattern
    • No stretch
    • Runs true to size

    Style Number/Barcode: 06503-0991

    Category Name: Vacation Looks

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance