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.

  • Play All Day Platforms
    Play all day in these beautiful nude platforms! Featuring an open toe and an adjustable ankle strap with a gold toned pin buckle closure. These beauties are composed of a nude matte faux leather material and the heel is a braided rope. We are loving the natural hues of these platforms that make it easy to pair with any outfit day or night!

    Runs a half size bigger.

    Style Number/Barcode: 07401-2076

    Category Name: Vacation Looks

    Price: $26.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Chic Aesthetic Five-Pack Bracelet Set

    The bracelet set features five bracelets with varying chic designs including a sleek snake chain, a trendy disc chain, a dainty paperclip chain accented with beading and faux pearls, a flat chain, and a classic paperclip chain. Style with hoop earrings.

    Fit & Features

    • Five-pack bracelet set
    • Snake chain
    • Disc chain
    • Dainty paperclip chain with beading and faux pearls
    • Flat chain
    • Paperclip chain
    • Adjustable lobster clasp closures

    Style Number/Barcode: 07003-0571

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • On The Rise Platform Heels

    Elevate your look in these statement making heels! The heels feature an open back, an adjustable ankle strap, wide crisscross straps, a peep toe, a wide platform and a wooden stacked heel. They are composed of a faux nubuck material and a faux leather insole lining.

    Style Number/Barcode: 07401-0009

    Category Name: Vacation Looks

    Price: $23.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Krystal Formal Floral Open Back Dress
    Special Occasion 

    Make a captivating entrance in florals! Krystal enchants the room with her sleeveless bodice, square neckline and bold open back with a lattice back. Her slim fit bodice leads to a sweeping floor length      A Line silhouette. Her all over floral print features pink and mauve hues that complement the ivory background. 

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-6777

    Category Name: Vacation Looks

    Price: $21.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • New Heights Strappy Wedge Heels

    Take your summer style to new heights with these must have wedge heels. They feature a multi strap design, a back zipper closure, and a high wedge platform heel.The best part is that their natural tan color can be paired with everything!

    Style Number/Barcode: 07406-0001

    Category Name: Vacation Looks

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Must Have Faux Leather Clutch

    This sleek faux leather clutch is def a must have! It features an envelope design with a fold over magnetic closure, a gold metal accent, a single interior zippered pocket, and links to attach an included gold chain to easily convert it to a crossbody. The black hued clutch is composed of a faux leather material with a woven lined interior.

    Style Number/Barcode: 07203-1789

    Category Name: Vacation Looks

    Price: $10.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Garden Groove Maxi Dress

    Pretty as a picture and primed for party-going! This icrepe maxi embodies chic warm-weather dressing. Maxi features a sleeveless bodice, deep V neckline, back zipper, banded waist with removable tie, and a high-low curved hem. Dress is lined and offers a modest amount of stretch.

    Style Number/Barcode: 05101-8846

    Category Name: Vacation Looks

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pearl Bobby Pins Set

    Show off that blinding highlight with these adorable pearl adorned gold bobby pins! The set features four pins, two of them with a straight row of pearls and the other two with a chic twisted row.

    Style Number/Barcode: 07006-0007

    Category Name: Vacation Looks

    Price: $2.97 $10.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go-To Pointy Flats
    Toe the line between pretty and polished with these versatile black slip-ons. Shoes feature a pointy toe, flat sole, and open back. Shoes are made from a soft, faux suede material with a faux leather insole.

    Style Number/Barcode: 07405-0000

    Category Name: Vacation Looks

    Price: $13.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Marlena Floral Chiffon Gown
    Special Occasion

    Perfect for parties, weddings, and evenings out, our lovely Marlena gown embodies elegance in navy floral chiffon. She features adjustable spaghetti straps, a draped empire-style bodice with V neckline, a back zip with hook-and-eye closure, and a full A-line wrap skirt with side tie. Marlena is fully lined and made from a semi-sheer woven material with little to no stretch.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-0073

    Category Name: Vacation Looks

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Plus Floral Fascination Midi Dress

    Fascinate and charm in gorgeous florals! This midi dress features a sleeveless bodice, a plunging V neckline, narrow adjustable strap and a pretty pink floral print throughout! Dress is composed of a slightly sheer smooth knit fabric that offers a bodycon curve hugging fit with a moderate stretch.  

    Style Number/Barcode: 15101-0079

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Persuasion Layered Skater Dress
    Persuade them all in pretty florals! This fun skater dress features an ivory hue, a plunging V neckline, narrow straps and a double layered skater skirt. The all over floral print features pink florals with green foliage. Dress is composed of a scuba knit fabric that offers a form hugging fit.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-8727

    Category Name: Vacation Looks

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dainty Ring Variety Pack

    Make a simply stunning statement with a hint of gold! This variety pack features 14 dainty gold hued bands to easily stack or wear alone.

    Style Number/Barcode: 07004-0986

    Category Name: Vacation Looks

    Price: $10.00 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Braid In The Shade Dress
    Color-saturated hues and retro flair lend this skater-style red mini its easy appeal. Dress features a halter neck with deep V, banded waist with cutout and two rows of braid trim, a braided clasp back, and a swing-y A-line skirt with back zip. Dress is partially lined and made from a soft, crepe-like woven material with little to no stretch.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0182

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Braid For Shade Maxi Dress
    Elegantly subdued hues and sophisticated cut lend this maxi its easy appeal. Dress features a halter neck with deep V, banded waist with cutout and two rows of braid trim, a braided clasp back, and an A-line skirt with back zip. Dress is partially lined and made from a soft, crepe-like woven material with little to no stretch.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0181

    Category Name: Vacation Looks

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortlessly Cool Mid-Rise Camo Cargo Shorts

    These effortlessly cool camo cargo shorts feature a mid-rise waist paired with a mid-thigh length relaxed fit. The cargo-style side pockets add some trendy edge to the casual silhouette.

    Fit & Features

    • Camo-printed cotton woven fabric, no stretch
    • Mid-rise waist with belt loops
    • Hidden front zipper with button closure
    • Two front pockets, two cargo side pockets, two faux back pockets
    • Mid-thigh length, relaxed fit
    • Shorts in size small have a 10" front rise with an 8" inseam
    • Runs true to size

    Style Number/Barcode: 06303-0289

    Category Name: Vacation Looks

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life's A Beach Mesh Dress

    Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.

    Style Number/Barcode: 05102-0158

    Category Name: Vacation Looks

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wild Thoughts Thigh-Slit Midi Dress

    Preen, play, and prowl in this body-skimming leopard print midi dress. Dress features adjustable spaghetti straps, back zip, and a thigh-high slit. Dress is lined and made from a satin-like fabric with little to no stretch.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0082

    Category Name: Vacation Looks

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffled In Love Sleeveless Dress
    Keep it lovely in ruffles in this stunning dress! It features a sleeveless square neckline, narrow shoulder straps and a midi length silhouette with an asymmetrical ruffled hem. Dress is composed of a stretchy crepe fabric that offers a form hugging fit.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0359

    Category Name: Vacation Looks

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Crossed In Florals Midi Dress

    Get crossed up in pretty florals as you stun in this gorgeous dress! It features a sleeveless bodice, and a plunging V neckline with adjustable cross-straps. The relaxed fit bodice leads to a curve hugging asymmetrical skirt accented with ruching details and a high side slit. The all over floral print features pink with white hues. Dress is composed of a smooth knit fabric that offers a curve hugging fit.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-4032

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Stunning LBD
    Keep it sleek and stunning in this LBD! It features a sleeveless bodice, a square neckline and wide shoulder straps that lead to an open back design with multi narrow cross straps. The relaxed fit bodice leads to a curve accentuating midi length silhouette. Dress is composed of a ponte-like fabric that offers a moderate stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05103-3528

    Category Name: Vacation Looks

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tied With Style Mini Dress
    Make your look all tied together with style with this summer ready mustard yellow mini dress! It features a sleeveless strapless bodice with a square neckline, a tie front belt, side ruched detailing, and a front envelope hem. The dress is composed of a crepe fabric with moderate stretch.

    Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

    Style Number/Barcode: 05102-3919

    Category Name: Vacation Looks

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Vibes Gauzy Mini Dress
    Feel the heat while keeping it cool in this gauzy olive skater dress. Dress features a deep V at front and back, side bar cutouts, an elasticated waist, and an all-over crinkle effect. Dress is made from a rayon fabric with moderate stretch. Dress is semi-sheer and unlined.

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-3847

    Category Name: Vacation Looks

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smocked In Spring Florals Dress
    Spring into the season with gorgeous florals! This dress features an ivory color, an off the shoulder neckline with a ruffled trim, a sweetheart bust and smocked side panels. The all over floral print features pink and green hues to create the perfect spring time look! Dress is composed a lightweight woven fabric that offers a curve hugging fit with minimal stretch. 

    Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

    Style Number/Barcode: 05102-0010

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance