Vacation Dresses & Outfits

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STYLE SPOTLIGHT

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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.

  • Golden Hour Shell Toe Ring Set

    Serving seaside glam with zero sand required. This 3-piece shell ring set brings the beach to your fingertips—literally. Stack 'em, mix 'em, or wear solo for a subtle flex.

    Fit & Features

    • Starfish, cowrie, and conch shell charms
    • Coastal-inspired accents
    • Pack includes three toe-rings

    Style Number/Barcode: 07004-000032

    Category Name: Vacation Dresses & Outfits

    Price: $6.90

    Availability: In Stock

    Available Color: GOLD

    Available Size: NS

  • Adorable Basic Scoop Neck Seamless Crop Top

    You'll always feel adorable in this basic crop top perfect for layering or styling on its own! The top is crafted from a seamless knit fabric offering plenty of stretch and comfort. It features a flattering scoop neckline, shoulder straps, and a fitted crop hem. Complete the look in denim shorts.

    Fit & Features

    • Seamless knit fabric, moderate stretch
    • Scoop neckline
    • Shoulder straps
    • Fitted crop length
    • Runs true to size

    Style Number/Barcode: 07109-0408

    Category Name: Vacation Dresses & Outfits

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bow And Tell Floral Slide Sandals

    Serving garden party glam with zero effort. These floral bow slides are playful, comfy, and practically begging for a vacay moment (or brunch pic).

    Fit & Features

    • Round toe
    • Bow strap
    • Flat sole
    • Floral print
    • Faux leather insole
    • Runs true to size

    Style Number/Barcode: 07404-000015

    Category Name: Vacation Dresses & Outfits

    Price: $22.90

    Availability: In Stock

    Available Color: MULTI

    Available Size: 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 10

  • Chill Vision Small Rectangle Sunglasses

    For the days when you’re chill, but still need to serve a look. These small rectangle sunglasses are the perfect low-key statement for brunch hangs, solo city strolls, or golden hour selfies.

    Fit & Features

    • Small rectangular-shaped design
    • Plastic frame with glossy finish
    • Thin arms
    • Flexible nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000059

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

  • Vacay Dream Floral Strappy Maxi Dress

    POV: You just entered the group chat looking like a vacay dream. This mesh maxi dress hugs in all the right places with a strappy back that turns heads on vacation and summer parties!

    Fit & Features

    • Tropical floral print, mesh-lined fabric, moderate stretch
    • V-neckline
    • Bungee spaghetti straps
    • Strappy open back
    • Form-hugging fit
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000389

    Category Name: Vacation Dresses & Outfits

    Price: $49.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L, XL

  • Denim Diva Square Toe Block Heels

    Fall head over heels for these denim block heels! Strut like a diva in these shoes featuring a square toe, a wide band, a block heel, and a luxe fit cushioned faux leather insole for comfort. Complete the look with a trendy handbag for any occasion!

    Fit & Features

    • 3" Block Heel
    • Square toe
    • Wide band
    • Luxe fit cushioned faux leather insole
    • Denim material
    • Runs true to size

    Style Number/Barcode: 07401-4885

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meet Me in the Meadow Chiffon Floral Maxi Dress

    Easy, breezy, and made for photoshoots and parties. This strapless chiffon maxi dress with a smocked bodice and floral print gives off-carefree weekend energy with a soft, boho vibe.

    Fit & Features

    • Floral print, chiffon fabric, short woven lining
    • Strapless smocked bodice
    • Flowy silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000107

    Category Name: Vacation Dresses & Outfits

    Price: $52.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Unique Addition Strapless Cut Out Tube Crop Top

    A chic strapless tube top makes a unique addition to your fashion lineup! The cutest date or night-out top features a strapless neckline, a trendy side cutout with an adjustable drawstring, and an asymmetrical cut cropped hem. Complete the look in a cute mini skirt and your favorite heels.

    Fit & Features

    • Soft knit stretchy fabric
    • Strapless neckline
    • Side cutout, adjustable drawstring
    • Asymmetrical cut cropped length
    • Runs true to size

    Style Number/Barcode: 06001-5377

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Juicy Drama Cherry Earrings

    These cherry earrings know how to steal the spotlight. Serve juicy drama with every head turn, whether you're posting or partying!

    Fit & Features

    • Cherries with sleek stems
    • Pull-through design

     

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

    Style Number/Barcode: 07001-000098

    Category Name: Vacation Dresses & Outfits

    Price: $9.90

    Availability: In Stock

    Available Color: BLOOD, RED

    Available Size: NS

    Product Badge:
    • Best Seller
  • Minimalist Moment Two-Pack Bracelet Set

    When your wrists need a glow-up. This two-pack bracelet set brings sleek, sculptural energy that’s perfect for stacking or wearing solo.

    Fit & Features

    • Two-pack bracelet set
    • High-shine metal material
    • Sleek, structured designs
    • Hinge clasp design

    Style Number/Barcode: 07003-000033

    Category Name: Vacation Dresses & Outfits

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Out Of Office Gradient Oversized Sunglasses

    These sunnies say “catch me on a yacht”—even if it’s just brunch. With oversized gradient lenses and glam hardware, these sunglasses are made for low-effort luxe and spontaneous selfies.

    Fit & Features

    • Rimless square-shaped oversized design
    • Metal chain-link detail on the arms
    • Flexible nose pads
    • Gradient-tinted lenses

    Style Number/Barcode: 07008-000058

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: PINK

    Available Size: NS

  • Everyday Beauty Sleeveless A-Line Mini Dress

    This sleeveless mini dress features a crew neckline, a flattering A-line silhouette, and a front slit accent. The soft rib knit fabric offers plenty of stretch and comfort.

    Fit & Features

    • Rib knit fabric, moderate stretch
    • Crew neckline
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5631

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drama Meets Paradise Floral Maxi Dress

    Giving goddess energy with every step you take. This mesh maxi dress clings in all the right places with a daring cowl neckline and a strappy open back made to be seen.

    Fit & Features

    • Floral print, mesh fabric, soft stretchy knit lining
    • Plunging cowl neckline
    • Strappy open back with hoop insert
    • Form-hugging fit
    • Flowy maxi hem and front slit
    • Runs true to size

    Style Number/Barcode: 05101-000352

    Category Name: Vacation Dresses & Outfits

    Price: $46.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Sweetly Coy V-Neck Slit Lace Crop Top

    Enhance your everyday style in this lace crop top featuring a V-neckline with a twist accent, spaghetti straps, and a center slit design. The lace-lined fabric offers stretch and a romantic look. 

    Fit & Features

    • Lace lined fabric, minimal stretch
    • V-neckline with twist
    • Spaghetti straps
    • Center slit 
    • Cropped length hem
    • Runs true to size

    Style Number/Barcode: 06001-5431

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Muse Square Sunglasses

    Serving low-effort luxe from sunrise to happy hour. These square sunglasses give effortless it-girl vibes with a sleek metal frame that pairs with everything from linen sets to poolside 'fits.

    Fit & Features

    • Curved square-shaped design
    • Thin metal frame
    • Thin arms
    • Flexible nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000055

    Category Name: Vacation Dresses & Outfits

    Price: $11.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: NS

  • Beachy Vibes Bell Sleeve Tie-Front Top

    This airy lightweight knit tie-front top gives off those effortless beachy vibes! It features a scoop neckline, a dual tie-front design, long flared bell sleeves, a cute scalloped front hem, and a mid-length, relaxed fit. The sheer knit fabric features a textured ribbed pattern. Layer over a basic bodysuit and style with light-wash denim.

    Fit & Features

    • Scoop neckline
    • Dual tie-front design, thin straps
    • Long bell sleeves
    • Scalloped front hem
    • Mid-length, relaxed fit
    • Sheer knit fabric, textured ribbed pattern, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06202-0400

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruffle Repeat Lace Tube Mini Dress

    She’s sleek up top, party on the bottom—aka your new go-to for nights that need a little extra twirl. The strapless neckline and tiered ruffles make it an easy yes for going out.

    Fit & Features

    • Lace fabric, stretchy knit lining
    • Strapless tube neckline
    • Form-hugging fit
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000171

    Category Name: Vacation Dresses & Outfits

    Price: $48.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Sangria Sunset Strapless Paisley Satin Crop Top

    The perfect paisley satin crop top to wear during sunset cocktail hour! Crafted from a silky satin fabric with a summery paisley print, this crop top elevates every outfit. It features a strapless neckline and stretchy smocked back, a flirty tie design, and a pointed cropped hem that flaunts your figure. Complete the look in denim jeans and strappy sandals.

    Fit & Features

    • Paisley print, satin fabric, no stretch
    • Strapless neckline
    • Tie back design, smocked back
    • Pointed cropped length
    • Runs true to size

    Style Number/Barcode: 06003-2545

    Category Name: Vacation Dresses & Outfits

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Low Effort Luxe Retro Sunglasses

    Instant cool-girl mode: activated. These rectangular-shaped sunglasses are giving low-effort luxe with a sleek retro frame that pairs perfectly with chunky hoop earrings.

    Fit & Features

    • Rectangular-shaped design
    • Thin metal frame
    • Thin metal arms
    • Flexible nose pads
    • Tinted lenses

    Style Number/Barcode: 07008-000025

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Done In One Zip-Front Tie-Waist Denim Romper

    Designed to be your new favorite done in one piece, this denim romper offers a cute and flattering style year-round! It's designed with classic short sleeves and collar neckline, a zip-front closure, two flap pockets and side pockets for convenience, a tie-waist belt that cinches your waistline, and a form-hugging fit. Complete the look with sleek hoop earrings and your fave sneakers!

    Fit & Features

    • Denim fabric, slight stretch
    • Short sleeves and collar neckline
    • Zip-front closure
    • Two flap pockets, side pockets
    • Tie-waist belt 
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06603-0400

    Category Name: Vacation Dresses & Outfits

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Barely Blushing Floral Mini Dress

    Soft girl, but make it sultry. This floral mini dress clings in all the right ways, with delicate straps and a dreamy texture that feels flirty but effortless!

    Fit & Features

    • Floral print, burnout texture, mesh fabric, stretchy knit lining
    • Scoop neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000165

    Category Name: Vacation Dresses & Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Lavish Leopard Print Palazzo Wide-Leg Pants

    Look lavish in these leopard palazzo pants boasting a mid-rise waist and wide-leg silhouette perfect for elevating your look. Style with a crop top and heels.

    Fit & Features

    • Smooth woven fabric, no stretch
    • Leopard print 
    • Elasticized mid-rise waist
    • Wide-leg pant
    • Pants in size small have an 11.5" front rise with a 28" inseam
    • Runs true to size

    Style Number/Barcode: 06402-1449

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cloud Cruisin’ Oval Frame Sunglasses

    These trendy oval sunglasses serve retro realness with a sleek plastic frame—perfect for iced lattes, low-effort fits, and avoiding eye contact with your ex.

    Fit & Features

    • Smooth plastic oval frames
    • Subtle curve with mid-coverage lenses
    • Classic Y2K-inspired silhouette

    Style Number/Barcode: 07008-000049

    Category Name: Vacation Dresses & Outfits

    Price: $10.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: NS

  • Love Of Details V-Neck Lace-Up Skater Dress

    Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.

    Fit & Features

    • Lace fabric line with stretchy knit
    • Adjustable spaghetti straps, V-neckline
    • Back zipper and hook-eye closure
    • Mesh lace-up bodice
    • Asymmetrical ruffles
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3436

    Category Name: Vacation Dresses & Outfits

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale