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.

  • Main Style Ribbed Knit Tank Mini Dress

    This adorable tank mini dress will be your new main style to create the cutest everyday looks! Designed with a stretchy ribbed knit fabric for comfortable wear, it features a sleeveless scoop neck and back, thin tank shoulder straps, and a bodycon silhouette to flaunt your figure. Pair this short dress with a denim jacket and sneakers for a coffee date with friends.

    Fit & Features

    • Stretchy ribbed knit fabric
    • Scoop neck and back
    • Thin tank straps
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1975

    Category Name: Vacation Looks

    Price: $8.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off Duty Babe Luxe Zip-Up Crop Hoodie

    Elevate your off-duty look babe in this luxe crop hoodie perfect for running errands or coffee runs! It features relaxed long sleeves with elasticized cuffs, a hooded neckline, front zipper closure, functional pockets, and a cropped elasticized hem on stretchy scuba knit fabric. Layer over a basic top and pants.

    Fit & Features

    • Relaxed long sleeves, elasticized cuffs
    • Hooded neckline
    • Front zipper closure
    • Functional pockets
    • Cropped elasticized hem
    • Stretchy and luxe scuba knit fabric
    • Runs true to size

    Style Number/Barcode: 06202-0379

    Category Name: Vacation Looks

    Price: $16.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Cute Striped Oversized Sweater

    Layer on this casual cute striped oversized sweater for an adorable everyday 'fit! It features a high crew neckline, long dolman sleeves with tapered cuffs, and a mid-length hem with a relaxed fit. The knit fabric features an all-over striped pattern with thick and thin stripes. Pair with your favorite go-to jeans and ankle booties.

    Fit & Features

    • High crew neckline
    • Long dolman sleeves, tapered cuffs
    • Mid-length hem
    • Oversized relaxed fit
    • Striped pattern, thick and thin stripes
    • Ribbed knit fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06005-1436

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Mermaid Mood Starfish and Seashell Earrings

    Giving vacation vibes, even if you’re just at brunch. These earrings mix starfish, seashells, and faux pearls for a playful, ocean-inspired finish.

    Fit & Features

    • Starfish and seashell designs
    • Faux pearl embellishments
    • Post-back closure

     

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

    Style Number/Barcode: 07001-000125

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Pearl-Fect Pick Sweater Maxi Dress

    Forever a perfect pick for your next chic soiree! This sweater maxi dress features long fitted sleeves, a plunge V-neckline, a center front faux pearl button-down along the bodycon silhouette, and a slit accent. The ribbed knit fabric offers a moderate stretch. Complete the look with pointed-toe booties.

    Fit & Features

    • Sweater ribbed knit fabric, moderate stretch
    • Long fitted sleeves
    • Plunge V-neckline
    • Center front faux pearl button-down
    • Bodycon fit
    • Front slit
    • Runs true to size

    Style Number/Barcode: 06005-1525

    Category Name: Vacation Looks

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Trendsetter Rhinestone Lace-up Skinny Jeans

    You'll be a trendsetting muse in these glam rhinestone-accented skinny jeans! They feature a high-rise waist, a rhinestone embellished lace-up front, a skinny-leg silhouette, and a form-hugging fit. The denim fabric offers a moderate stretch. Complete the look with sparkly mules.

    Fit & Features

    • High-rise waist
    • Rhinestone embellished lace-up front design
    • Skinny-leg silhouette
    • Five-pocket design, three belt loops
    • Front button, hidden zipper closure
    • Denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06602-0389

    Category Name: Vacation Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Style Warm Up Sweater Knit Dress

    Cozy up this season in style! This sweater mini dress is the best of both worlds featuring cozy dolman sleeves, a surplice v-neckline, belted tie-front waist, and a bodycon silhouette. The dress is composed of soft cable and rib-knit fabric that offers plenty of stretch. Style with knee-high boots to complete the look!

    Fit & Features

    • Dolman sleeves
    • Surplice v-neckline
    • Belted tie-front waist, belt loop accents
    • Bodycon silhouette, mini-length
    • Cable and rib-knit sweater fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1572

    Category Name: Vacation Looks

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Don't Tempt Me Textured Slit Crop Top

    Don't let your girls tempt you from taking this sultry crop top out for a good time! It features fitted long sleeves, an open V-neckline, a center front slit accent, and is composed of a textured sheer knit fabric. Complete the look in distressed denim jeans.

    Fit & Fetaures

    • Fitted long sleeves
    • Open V-neckline
    • Center front slit accent
    • Cropped hem
    • Textured sheer knit fabric
    • Runs true to size

    Style Number/Barcode: 06001-5267

    Category Name: Vacation Looks

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bold Allure One-Shoulder Cutout Waist Knit Midi Dress

    Bring the bold allure to your summer 'fits with this sultry cutout waist midi dress! Made with a lined stretchy ribbed knit fabric, the mid-length dress features a sleeveless one-shoulder neckline and a tank strap with a trendy twisted-back design. The asymmetric goes around the waist, accented with a chic O-ring cutout at the front. The midi-length hem is detailed with a high-cut side slit along the figure-flaunting bodycon silhouette. Style with lace-up sandals for a weekend getaway!

    Fit & Features

    • Stretchy ribbed knit fabric, knit lining
    • One-shoulder neckline, tank strap with twisted-back design
    • Asymmetric waist cutout
    • Front O-ring cutout
    • High side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5697

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunshine Livin' High Rise Palazzo Crochet Pants

    These crochet palazzo pants were meant for living under the sun! Whether you're heading to a festival or a getaway, these pants will keep you boho-cute. They feature an elasticized high-rise waist and a flattering relaxed silhouette. Complete the look with the matching top.

    Shop Matching Top: Sunshine Livin' Halter Crochet Crop Top

    Fit & Features

    • Crochet fabric lined with stretchy knit
    • High-rise elasticized waist
    • Relaxed silhouette
    • Runs true to size

    Style Number/Barcode: 06302-0823

    Category Name: Vacation Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paradise Bound Tropical Floral Satin Midi Dress

    You'll be ready to jet set off to paradise in this gorgeous tropical floral satin midi dress! The silky sleek satin woven fabric is accented with a blooming tropical floral print, an iconic look for your vacay getaway. The mid-length dress features a sleeveless V-neckline, adjustable spaghetti straps with a racer-back design, a flattering tie-back detail, and an asymmetric hanky hem with a flowy A-line silhouette for that effortless vibe. Style with hoop earrings and a layered necklace.

    Fit & Features

    • Tropical floral print
    • Non-stretch satin woven fabric with top knit lining
    • V-neckline
    • Adjustable spaghetti straps, racer-back design
    • Tie-back design
    • Asymmetric hanky hem, A-line fit
    • Runs true to size

    Style Number/Barcode: 05101-3468

    Category Name: Vacation Looks

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Chic Side Slit Skort

    Create a simply chic everyday outfit with this classic crepe skort. It features a high-rise waist, a back zipper closure, a mini-length overlay with a side slit, and fitted shorts. The crepe fabric offers a moderate stretch. Complete the look with a bodysuit and mules.

    Fit & Features

    • High-rise waist
    • Back zipper closure
    • Mini-length overlay, side slit
    • Fitted shorts
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06503-1038

    Category Name: Vacation Looks

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty In Fall Cable Knit Dress

    Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Open-back design
    • Midi-length hem
    • Soft cable knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1614

    Category Name: Vacation Looks

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Edgy Stretch Resin Bracelet

    A little shine, a lot of style. This resin stretch bracelet with sleek metal trim is the low-effort way to elevate any outfit—stack it up or let it stand alone.

    Fit & Features

    • Smooth resin material
    • Stretch elastic fit
    • Polished metal trim accents
    • Lightweight and comfortable
    • Please note color varies

    Style Number/Barcode: 07003-000110

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: BROWN, GREEN

    Available Size: NS

  • Paradise Awaits Cutout Tropical Knit Jumpsuit

    This sexy cutout tropical knit jumpsuit is a definite must when packing for your trip to paradise! The stretchy lightweight knit fabric showcases an eye-catching palm leaf print perfect for your dream vacay. It features a sleeveless plunging neckline with cross-front spaghetti straps and a halter tie-back design for a customized fit. The alluring waist cutouts lead to an open lower back for added sultry flair. The hip-hugging fit flows down to a relaxed wide-leg silhouette. Complete the look with strappy sandals.

    Fit & Features

    • Tropical printed knit fabric, lined bust, plenty of stretch
    • Plunging neckline with cross-front spaghetti straps, halter tie-back design
    • Waist cutouts, open back
    • Hip-hugging fit
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06502-2494

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style Knit Right Chenille Sweater

    You'll love styling this chenille crop sweater into your weekly outfit rotation! It features cozy long sleeves, a crew neck, and a striped color block pattern composed of a cable knit design. The ultra-soft chenille fabric has no stretch. Complete the look in boyfriend jeans for a cute and casual vibe!

    Fit & Features

    • Long sleeves
    • Crew neck
    • Striped color block pattern
    • Cropped hem
    • Cable knit design
    • Chenille fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06005-1562

    Category Name: Vacation Looks

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • City Streets Slouch Stiletto Boots

    Walk down the city streets like it's your runway in these chic slouch stiletto boots! They feature an above-the-ankle height with a trendy slouched design, a pointed toe, and a sleek stiletto heel. Style with a crossbody bag.

    Fit & Features

    • Above-the-ankle height
    • Slouchy silhouette
    • Partial inner zipper closure
    • Pointed toe
    • Stiletto heel
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07403-1592

    Category Name: Vacation Looks

    Price: $8.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Updated Chic High Rise Slit Linen Maxi Skirt

    Whether you're heading on vacation or out on the weekend, this linen maxi skirt will help you look chic all season! The high-rise waist and form-hugging fit flatter your figure while the adjustable front drawstring allows for a perfect fit. The high slit adds a touch of drama and the maxi-length hem exudes effortless style. Complete the look in a corset top and wedges.

    Fit & Features

    • Linen blend fabric, woven lining, no stretch
    • High-rise waist, side zipper and hook-eye closure
    • Adjustable front drawstring
    • High slit
    • Maxi-length, form-hugging
    • Runs true to size

    Style Number/Barcode: 06301-0188

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mixed Signals 50/50 Knee-High Boots

    Don't get your signals crossed, these knee-high boots are just what your closet needs! They feature an almond toe, low-block heel, side zipper, and are half faux suede and knit compression. Style with a chic handbag. 

    Fit & Features

    • Almond toe
    • Low-block heel
    • Side zipper
    • Knee-high length
    • Half faux suede, half knit compression
    • Runs true to size

    Style Number/Barcode: 07402-0696

    Category Name: Vacation Looks

    Price: $8.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Play My Song Lace Fringe Crop Top

    Move to the music in this lace fringe crop top at festivals, concerts, or your fave country bar!

    Fit & Features

    • Lace fabric, bust knit lining
    • Strapless neckline
    • Sheer fitted crop hem, fringe trim
    • Runs true to size

    Style Number/Barcode: 06001-000105

    Category Name: Vacation Looks

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sleek Energy Over The Knee Boots

    Embody a sleek fashion sense in these over-the-knee boots perfect for elevating your fit! They feature an almond toe, block heel, inner side zipper closure, and an adjustable drawcord. Complete the look in a trendy sweater dress.

    Fit & Feature

    • Almond toe
    • Block heel
    • inner side zipper closure
    • Over-the-knee length shaft
    • Adjustable drawcord
    • Faux leather material
    • Runs true to size

    Style Number/Barcode: 07402-0833

    Category Name: Vacation Looks

    Price: $4.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Call The Shots High-Rise Wide-Leg Pants

    Decide your fashion direction in these high-rise pants for creating unique and stylish outfits! They feature a flattering high-rise waist and a breezy wide-leg silhouette for comfort and chicness. Style with a crop top, earrings, and wedges!

    Fit & Features

    • Woven fabric with minimal stretch
    • High-rise waist, back elastic band
    • Wide-leg silhouette
    • Runs true to size

    Style Number/Barcode: 06402-1395

    Category Name: Vacation Looks

    Price: $12.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Making Waves Shell Claw Clip Set

    Not your average hair clip—these shell-shaped claws bring full glam to your grab-and-go moments. Whether you're throwing your hair up for errands or adding a little luxe to your vacation look.

    Fit & Features

    • Two-pack claw clip set
    • High-shine metal material
    • Seashell design

    Style Number/Barcode: 07006-000077

    Category Name: Vacation Looks

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let It Flow Crochet V-Neck Skater Dress

    Flowy and flirty! Twirl all day in this crochet V-neck skater dress featuring a sleeveless bodice with adjustable spaghetti straps, an open back with tie closure, and a tiered short hem. Composed of a gauze woven fabric with an inner lining. Finish the look in trendy mules.

    Fit & Features

    • Sleeveless bodice, crochet V-necklined
    • Adjustable spaghetti straps
    • Open-back, tie closure
    • Tiered short hem
    • Skater silhouette
    • Airy gauze woven fabric, inner lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4397

    Category Name: Vacation Looks

    Price: $21.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale