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.

  • Sultry Fave Halter Cowl Neck Floral Maxi Dress

    You'll always embody sultriness in this floral mesh maxi dress perfect for weddings or cocktail parties! The halter cowl neckline with tie adds a touch of charm, while the form-hugging silhouette highlights your curves. The maxi-length hem and floral print mesh fabric bring an elegant and romantic touch. Complete the look with rhinestone earrings and a clutch.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Halter cowl neckline with tie
    • Form-hugging silhouette
    • Maxi-length
    • Runs true to size

    Style Number/Barcode: 05101-3331

    Category Name: Vacation Looks

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stacked To Perfection Beaded Stretch Bracelets

    Level up your stack game with zero effort. These beaded stretch bracelets are giving luxe layering vibes with that cool-girl ease you love.

    Fit & Features

    • Multi-pack beaded bracelets
    • Varying sizes
    • Stretchy design

    Style Number/Barcode: 07003-000051

    Category Name: Vacation Looks

    Price: $13.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Flirt Sweetheart Lace Trim Skater Dress

    This sleeveless chiffon skater dress features a lace trim sweetheart neckline and bodice for flirty flair while the drop waist seam accentuates your curves along the mini-length skater silhouette. Perfect for a dressy brunch or party.

    Fit & Features

    • Sheer chiffon woven fabric with stretchy knit lining
    • Lace trim sweetheart neckline with bow detail, bust underwire
    • Adjustable lace trim shoulder straps
    • Partially smocked back with zipper and hook-eye closure
    • Lace trim bodice, drop waist seam
    • Mini-length skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3461

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Desert Daze Straw Cowboy Hat

    This straw cowboy hat is giving rodeo queen meets boho babe—lightweight, breezy, and made for your next sun-soaked photo dump.

    Fit & Features

    • Straw material
    • Woven design
    • Structured top
    • Wide curved brim
    • Thin twisted band, tie-back design

    Style Number/Barcode: 07302-000070

    Category Name: Vacation Looks

    Price: $11.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Read All About It Newspaper Bodycon Mini Dress

    Extra, extra read all about how fine you'll look in this newspaper print mini dress! This dress features a sweetheart neckline with lace trim and adjustable spaghetti straps for a perfect fit. The built-in padded underwire bust ensures support while the bodycon fit and mini-length hem create a flattering silhouette. Complete the look in a crop denim jacket.

    Fit & Features

    • Newspaper print, knit fabric with stretchy lining
    • Adjustable spaghetti straps
    • Sweetheart neckline with lace trim
    • Back zipper and hook-eye closure
    • Built-in padded underwire bust
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05103-5578

    Category Name: Vacation Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Smooth Talker Lace Bow Pleated Ponte Mini Dress

    Smooth ponte knit fabric shapes this sleeveless mini dress featuring a lace bow trim square neckline, spaghetti straps, and a fitted silhouette that leads to a pleated flare mini-length hem.

    Fit & Features

    • Smooth pointe knit fabric, minimal stretch
    • Lace bow trim square neckline
    • Spaghetti straps
    • Fitted silhouette
    • Pleated flare mini-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3661

    Category Name: Vacation Looks

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Of Mine Four Piece Bracelet Set

    Perfect for stacking or styling alone, this four piece bracelet set will add a chic finishing touch to any look. This versatile bracelet set features an array of complementary styles, some adorned with dazzling rhinestones and elegant faux pearls.

    Fit & Features

    • Four-piece bracelet set
    • One faux pearl bracelet, stretchy fit
    • One twisted chain bracelet, lobster clasp closure
    • One rhinestone embellished bracelet, toggle closure
    • One chain coin charm bracelet, lobster clasp closure

    Style Number/Barcode: 07003-000035

    Category Name: Vacation Looks

    Price: $12.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress

    Shine bright and serve a gorgeous aura in this strapless floral tie-dye maxi dress perfect for summertime soirees! The strapless neckline and lace-up back design exude effortless elegance, while the form-hugging fit accentuates your curves. The ruffled maxi-length hem adds a playful touch to this stunning dress. Complete the look with a ring set and sandals.

    Fit & Features

    • Floral tie-dye print, smooth knit fabric, moderate stretch
    • Strapless neckline
    • Lace-up back design
    • Form-hugging fit
    • Ruffled maxi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3277

    Category Name: Vacation Looks

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    Price: $9.97 $14.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    Price: $6.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    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 Looks

    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 Looks

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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 Looks

    Price: $14.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Cowgirl Colored Stone Straw Western Hat

    Top off your cowgirl core look with this straw western hat at bachelorettes, festivals, or country bar nights! Made from distressed straw material for a rustic feel.  Featuring a string tie bow adorned with a colorful stone and metal ball trim, this hat adds a touch of glam to the classic curved wide brim. Complete the look in cowboy boots.

    Fit & Features

    • String tie bow, colored stone and metal ball trim
    • Classic curved wide brim
    • Distressed straw material
    • Adjustable inner strings for a snug fit

    Style Number/Barcode: 07302-1604

    Category Name: Vacation Looks

    Price: $4.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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 Looks

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Shades Square Sunglasses

    Discover these trendy sunglasses perfect for any sunny day to keep your style on point! They feature a small square shape, tinted UV protective lenses, and comfortable arms and nose support. Complete the look with platform sneakers for a casual day out.

    Fit & Features

    • Small square shape
    • Tinted UV protective lenses
    • Comfortable arms and nose support

    Style Number/Barcode: 07008-1089

    Category Name: Vacation Looks

    Price: $9.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Feeling Sleeveless Bubble Hem Mini Dress

    A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.

    Fit & Features

    • Knit fabric, moderate stretch
    • Crew neckline
    • Form-hugging fit
    • Drop waist seam, bubble mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5873

    Category Name: Vacation Looks

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Reusable Gel Lift Pasties

    These gel bra pasties create the perfect lift and nipple coverage for a smooth look. The supportive sticky bra design with its adhesive interior gently lifts the breasts and perfectly covers the nipples for a seamless look. Wear these bra pasties underneath an open-back halter top or strapless cocktail dress with a smooth shapewear style for the ultimate flawless ensemble. Wear with a sleeveless top and a cute pair of denim for your next-day date.

    Fit & Features

    • One pair
    • Gel pasties
    • Reusable, can be worn up to 25 times
    • Provide smoothing, lifting, and supporting effects

     

    Fashion tape, adhesive bras, adhesive panties, pasties, cosmetics, and lingerie are considered final sale merchandise. FINAL SALE and CLEARANCE merchandise may not be returned or exchanged.

    Style Number/Barcode: 07101-0272

    Category Name: Vacation Looks

    Price: $9.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: NS