Vacation Looks
Vacation outfits should feel as effortless as your out-of-office vibe. Think long floral dresses that move with the breeze, easy cover-ups for poolside lounging, and bold two-piece sets that pop in every photo. From beachy maxis that bring instant elegance to denim shorts that nail casual cool, each piece blends comfort with style so you never have to choose between the two. These looks are made for packing light, looking chic, and serving up Instagram-worthy vacation moments.
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      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.
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                 Sultry Fave Halter Cowl Neck Floral Maxi Dress Sultry Fave Halter Cowl Neck Floral Maxi DressYou'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
 
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                 Stacked To Perfection Beaded Stretch Bracelets Stacked To Perfection Beaded Stretch BraceletsLevel 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
 
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                 Such A Flirt Sweetheart Lace Trim Skater Dress Such A Flirt Sweetheart Lace Trim Skater DressThis 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
 
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                 Desert Daze Straw Cowboy Hat Desert Daze Straw Cowboy HatThis 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
 
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                 Read All About It Newspaper Bodycon Mini Dress Read All About It Newspaper Bodycon Mini DressExtra, 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
 
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                 Smooth Talker Lace Bow Pleated Ponte Mini Dress Smooth Talker Lace Bow Pleated Ponte Mini DressSmooth 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
 
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                 Love Of Mine Four Piece Bracelet Set Love Of Mine Four Piece Bracelet SetPerfect 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
 
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                 Gorgeous Aura Strapless Floral Tie-Dye Maxi Dress Gorgeous Aura Strapless Floral Tie-Dye Maxi DressShine 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
 
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                 Adorable Basic Scoop Neck Seamless Crop Top Adorable Basic Scoop Neck Seamless Crop TopYou'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
 
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                 Denim Diva Square Toe Block Heels Denim Diva Square Toe Block HeelsFall 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
 
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                 Unique Addition Strapless Cut Out Tube Crop Top Unique Addition Strapless Cut Out Tube Crop TopA 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
 
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                 Everyday Beauty Sleeveless A-Line Mini Dress Everyday Beauty Sleeveless A-Line Mini DressThis 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
 
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                 Sweetly Coy V-Neck Slit Lace Crop Top Sweetly Coy V-Neck Slit Lace Crop TopEnhance 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
 
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                 Beachy Vibes Bell Sleeve Tie-Front Top Beachy Vibes Bell Sleeve Tie-Front TopThis 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
 
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                 Sangria Sunset Strapless Paisley Satin Crop Top Sangria Sunset Strapless Paisley Satin Crop TopThe 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
 
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                 Low Effort Luxe Retro Sunglasses Low Effort Luxe Retro SunglassesInstant 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
 
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                 Done In One Zip-Front Tie-Waist Denim Romper Done In One Zip-Front Tie-Waist Denim RomperDesigned 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
 
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                 Minimalist Moment Two-Pack Bracelet Set Minimalist Moment Two-Pack Bracelet SetWhen 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
 
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                 Lavish Leopard Print Palazzo Wide-Leg Pants Lavish Leopard Print Palazzo Wide-Leg PantsLook 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
 
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                 Everyday Cowgirl Colored Stone Straw Western Hat Everyday Cowgirl Colored Stone Straw Western HatTop 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
 
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                 Love Of Details V-Neck Lace-Up Skater Dress Love Of Details V-Neck Lace-Up Skater DressFall 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
 
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                 Trendy Shades Square Sunglasses Trendy Shades Square SunglassesDiscover 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
 
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                 Weekend Feeling Sleeveless Bubble Hem Mini Dress Weekend Feeling Sleeveless Bubble Hem Mini DressA 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
 
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                 Reusable Gel Lift Pasties Reusable Gel Lift PastiesThese 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 Product Badge:- Best Seller