Black Vacation Outfits
Black vacation outfits are the ultimate power move for your getaway lineup—effortlessly chic, totally mysterious, and always ready for a little mischief. Whether you’re plotting rooftop cocktails or spontaneous adventures, these looks have your back and then some. Slip into all-black everything and let your confidence do the talking—because every Windsor girl knows the best memories are made when you show up bold, fearless, and just a little extra.
$32.90
A sheer black crochet knit topper with long flared sleeves and an ultra-cropped hem for layering.
$46.90 - $49.90
A black high-waist cargo jogger with metal ring trims and elastic hem for a sporty look.
$42.90
A sleek black knit midi dress with a cowl neckline, high slit, and fitted A-line silhouette.
$34.90 - $42.90
A black crepe halter jumpsuit with a plunging V-neckline and flattering straight-leg pants.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$36.90
A black knit midi dress with a sleeveless square neckline, ruching, and pleated mermaid silhouette.
$46.90
A chic black knit jumpsuit featuring a strapless neckline and flattering wide-leg silhouette.
$44.90
A sultry black floral maxi dress with a V-neckline and form-hugging silhouette, perfect for vacations.
$44.90
A strapless black lace romper featuring a pleated mini hem and flattering, waist-accentuating silhouette.
$49.90
A sultry black knit jumpsuit featuring a cutout bodice and wide-leg silhouette.
$34.90
A black denim skort with a mid-rise waist, bodycon fit, and edgy studded pocket trim.
$15.97 $34.90 54% off
A sheer black chiffon kimono featuring relaxed short sleeves and a tie-front open design.
$39.90
A black tropical print maxi skirt in stretchy knit fabric featuring a high front slit and flowy silhouette.
$26.90
A pair of black crochet knit shorts featuring a sheer design and low-rise drawstring waist.
$34.90
A pair of black tropical print wide-leg pants crafted from stretchy knit fabric for a luxe vacation vibe.
$29.90
A black floral mesh crop top featuring long sleeves, a tie-front closure, and a dramatic ultra-cropped hem.
$29.90
A black tropical print crop top featuring a tie-front closure, long sleeves, and stretchy knit fabric.
$39.90
A black floral mesh maxi skirt featuring a high-rise waist, dramatic front slit, and attached panty lining.
$39.90
A chic pair of black high-rise skinny pants in coated faux leather with minimal stretch.
$39.90
A sultry black formal dress with rhinestone straps, a high slit, and a curve-hugging silhouette.
$35.90
A black knit bodycon mini dress with a pleated cowl neckline and spaghetti straps.
$46.90
A black strapless romper with rhinestone embellishments and a form-hugging silhouette for standout style.
$39.90
A trendy black lace romper with a plunging V-neck and ruffled mini-length overlay.
$44.90
A chic black skater romper with a lace back, wrap-front, and adjustable spaghetti straps.
$69.90
A bold black mesh mini dress with studded rhinestones, ruching, and sheer long sleeves.
$29.90
A black low-rise shorts with rhinestone embellishments and stretchy cotton-blend knit fabric.
$26.90
A black knit halter crop top featuring an open back, beaded accents, and a sheer cropped hem.
$59.90
A black woven glitter knit mini dress with a strapless sweetheart neckline and detachable bow accent.
$89.90
A black bodycon dress with faux pearl beading, sheer sleeves, and a plunging sweetheart neckline.
$36.90
A chic black mini dress with a pleated cowl neckline and flowy A-line silhouette.
$9.97 $42.90 77% off
A chic black strapless midi dress with a cowl-draped neckline and asymmetric hem for allure.
$64.90
An elegant black mesh dress featuring an off-the-shoulder neckline, sheer long sleeves, and a high side slit.
$34.90
A black crochet knit crop top featuring flare long sleeves and a flattering tie-front design.
$64.90
A luxe black velvet skater dress with an off-the-shoulder neckline and pleated drop-waist design.
$44.90
A black midi dress with a floral flocked velvet pattern, halter neckline, and high side slit.
$74.90
A black mesh mermaid dress featuring a plunging halter neckline, high side slit, and elegant ruching.
$49.90
An edgy black romper featuring a strapless corset bodice, grommet trim, and ruffled mesh overlay.
$19.97 $64.90 69% off
A black knit mermaid dress with an off-the-shoulder neckline and ruched bodice for formal occasions.
$64.90
A black velvet mermaid dress with a glittery corset bodice and adjustable spaghetti straps.
$29.97 $59.90 50% off
A stunning black lace dress featuring a high side slit and an elegant open-back design.
$9.97 $49.90 80% off
A black velvet mini dress with a twist accent, open back, and chic side slit.
$9.97 $44.90 78% off
A black velvet glitter mini dress with a one-shoulder neckline and wrap-around waist cutout.
$42.90
A black glitter mini dress with off-the-shoulder neckline, sheer sleeves, and ruching details.
$19.97 $79.90 75% off
A black mermaid dress with a plunging V-neckline, ruching, and smooth knit fabrication.
$59.90
A black mini dress with sequin embroidery, dual waist cutouts, and a bold open back.
$29.90
A black knit mini wrap skort featuring a belted side detail, hidden fitted shorts, and moderate stretch.
$34.90
A black glitter knit mini dress with a strapless neckline and bodycon fit for standout style.
$29.90
A black sheer lace dress featuring a sweetheart neckline and partially open back with tie straps.
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Lavish yourself with a luxe formal dress that elevates your special occasion outfit! Cheyenne features a one-shoulder neckline, a wired V-neck bust, a fitted long sleeve, a high side slit on the floor-length hem, and a curve-hugging A-line silhouette. The long dress is composed of a lined velvet fabric that offers a moderate stretch. Complete the look with rhinestone heels and a sphere clutch. Fit & FeaturesOne-shoulder neckline, wired V-neck bust, Fitted long sleeve, High side slit, floor-length hem, A-line silhouette, Lined velvet fabric, Form-hugging fit, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cheyenne Formal One-Shoulder Velvet Dress in Black-2 | Size: S | Rhinestone/Velvet Fabric
Dare to stun in the Jamie satin formal dress crafted with silky satin fabric for a gorgeous sheen. The bold plunge halter neckline and open lace-up back will turn heads while the fitted column silhouette flaunts your curves. Fit & FeaturesSilky satin fabric, short knit stretchy lining, Plunge halter V-neckline, shoulder straps, padded bra cups, Lace-up open back, lower zipper with hook-eye closure, High side slit, Fitted column silhouette, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, galas, and black-tie soirees. Free Shipping on All Orders Over $75. | Windsor Jamie Lace-Up Satin Formal Column Dress in Red | Size: XS | Knit Fabric/Satin Fabric
Sophistication meets sultry on the Marjorie formal dress perfect for cocktail parties and dressy family get-togethers. She features sheer chiffon peasant long sleeves, a square neckline, a bodycon silhouette, and a front ruched seam leading to the skin-flaunting slit along her midi-length hem. The formal dress is composed of a lined crepe fabric with a moderate stretch. Style with a chic clutch and heels to complete the look! Fit & FeaturesSheer chiffon peasant long sleeves, square neckline, Front ruched seam, slit detail, Bodycon silhouette, Midi-length hem, Lined crepe fabric, moderate stretch, Bra-friendly design, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Marjorie Formal Chiffon Sleeve Midi Dress in White | Size: XL | Chiffon/Crepe Fabric
A chic staple skater dress featuring a flirty off-the-shoulder folded neckline and a short-length perfect for styling with boots or heels. Fit & FeaturesRibbed knit fabric with plenty of stretch, Off-the-shoulder neckline, fold-over accent, Long fitted sleeves, Short-length hem, Skater silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Staple Ribbed Knit Skater Dress in Black | Size: XS | Knit Fabric
The Gwendolyn glitter knit bow-back mermaid dress will have you sparkling up the night with a glamorous allure! Make your entrance in this floor-length gown designed to turn heads with a curve-flaunting mermaid fit and backless design. Fit & FeaturesGlitter knit fabric, moderate stretch, Square neckline, spaghetti straps, Backless design, high waist seam, Bow-back accent, floor-length train, Floor-sweeping hem, mermaid silhouette, Runs true to size, Extra glitter for maximum sparkle - may have some natural fallout, Where to Wear:Weddings, black tie galas, formal dances, big birthday events, rehearsal dinners, engagement parties, red carpet occasions, upscale glam parties Free Shipping on All Orders Over $75. | Windsor Gwendolyn Glitter Knit Bow-Back Mermaid Dress in Pink | Size: S | Knit Fabric
A sparkling sequin scroll pattern adds beauty and shine to the glamorous Saige formal long dress! With a lace-up back that turns heads, a curve-hugging mermaid silhouette, and a high slit for a gorgeous look. Fit & FeaturesSequin scroll pattern, mesh fabric, stretchy full knit lining, Sleeveless plunge V-neckline, padded bust, Spaghetti straps, open lace-up back detail, Back zipper and hook-eye closure, Mermaid silhouette, floor-length hem, Runs true to size, Where to Wear:Prom, black-tie events, glam functions, and parties. Free Shipping on All Orders Over $75. | Windsor Saige Formal Sequin Lace-Up Mermaid Dress in Lavender | Size: XS | Knit Fabric/Mesh Fabric/Mesh Fabric
Chandler Strapless Lace-Up Sequin Formal Dress in Neon Orange
$19.97 $99.90
80% off
Chic with an elegant bold flair, the Chandler sequin formal dress was made to bring the drama. The floor-length dress has an alluring open back with a strappy lace-up design for customizable wear and a high slit for effortless allure. Fit & FeaturesSheer mesh fabric, full knit lining, moderate stretch, Strapless sweetheart neckline, angled design, structured boning, Open back, strappy lace-up design, tie closure, Fitted bodice, high waist seam, lower back zipper, hook and eye closure, Floor-length hem, high front slit, A-line silhouette, Sequin embroidery, scroll pattern, Runs true to size, Where to Wear:Prom, black-tie galas, red-carpet events, and fancy soirees. Free Shipping on All Orders Over $75. | Windsor Chandler Strapless Lace-Up Sequin Formal Dress in Neon Orange | Size: S | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
The Lucille formal satin dress will have you looking and feeling radiant and luxe! The dress captivates with a lace-up back, mermaid silhouette, and high front slit for effortless allure. Fit & FeaturesLined satin knit fabric, minimal stretch, Sleeveless square neckline, padded bust, adjustable spaghetti straps, Open lace-up back design, zipper and hook-eye closure, Fitted bodice, front ruched seam, high-cut slit, Mermaid silhouette, floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, black tie galas, red-carpet events, nights at the opera or theatre, big milestone celebrations Free Shipping on All Orders Over $75. | Windsor Lucille Formal Satin Mermaid Dress in Coral | Size: L | Knit Fabric/Satin Fabric
Bring the romantic allure to the evening affair in the Marylou lace mesh plunge formal dress! She embodies flirtatious style in a sleeveless plunge V-neckline with a built-in padded bust and adjustable spaghetti straps on her empire waist bodice. The sparkly embroidered lace mesh fabric effortlessly flows into a floor-length silhouette with a high-side slit to showcase some legs. She also features a curve-conscious silhouette to flaunt your stunning figure! Complete the look in an elegant hair clip. Fit & FeaturesPlunge V-neckline, adjustable spaghetti straps, Adhesive bra recommended, built-in padded bust, High side slit, back zipper, hook and eye closure, Empire waist, form-fitting silhouette, Floor-length hem, Sparkly embroidered lace mesh fabric, full knit lining, moderate stretch, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Marylou Lace Mesh Plunge Neck Formal Dress in Black | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
Spend an evening in the timeless elegance of the Alicia floor-length formal dress and feel like a work of art! The side ruched seams accentuate your curves along the mermaid silhouette, and the high front slit adds a touch of drama to the floor-length hem. Fit & FeaturesSmooth knit fabric lined with stretchy knit, Padded bra cups, Back zipper and hook-eye closure, High front slit, Mermaid silhouette, Runs true to size, Where to Wear:Prom, galas, black tie parties, weddings, bridesmaids, nights at the theatre and opera, red-carpets Free Shipping on All Orders Over $75. | Windsor Alicia Off-The-Shoulder Mermaid Formal Dress in Brown | Size: M | Knit Fabric
Black Vacation Outfits
When it comes to crafting the ultimate getaway vibe, nothing says “main character energy” like a black vacation outfit that’s equal parts effortless and iconic. Whether you’re jetting off for a girls’ trip, planning a dreamy baecation, or just treating yourself to a little R&R, black is the shade that never lets you down. It’s the go-to for the girl who wants to look pulled together from sunrise mimosa to late-night rooftop party—no outfit changes required. Imagine yourself lounging poolside in a sleek black vacation set that moves with you from cabana to cocktail hour, or twirling through a bustling market in a flowy black vacation dress that keeps you cool and collected, even when the temperature is rising. Black is that secret weapon in your suitcase: it doesn’t show the travel wrinkles, it’s basically spill-proof (hello, sangria!), and it instantly elevates every selfie. Plus, it’s the color that makes everyone look like a total knockout, whether you’re going for mysterious goddess or playful trendsetter.
Choosing the right black vacation outfit is all about dialing up the confidence and dialing down the stress. If you’re shopping for yourself, think about versatility—can you mix and match pieces for endless outfit combos? Is it comfy enough for that cross-country flight but glam enough for dinner with a view? If you’re shopping for your bestie, sister, or even your mom (because let’s be real, everyone deserves to feel like a star on vacay), a black vacation dress is a gift that’s guaranteed to get major mileage. These looks are made for making memories—whether you’re snapping pics on a sunset cruise, dancing barefoot on the sand, or just soaking up the good vibes with your ride-or-die crew. And let’s not forget the practical perks: black is ultra-flattering, hides last-minute packing chaos, and always looks expensive, even when you’re living that affordable luxury life. Pair your picks with chunky sandals, statement earrings, and a swipe of bold lipstick, and you’re ready to take on every adventure your escape throws your way.
No matter where your wanderlust takes you, the right black vacation set is like your personal hype squad—cheering you on, keeping you cool, and making every moment feel a little more cinematic. The best part? These are the pieces you’ll reach for long after your trip is over, whether you’re brunching with the girls or reliving your favorite memories in your camera roll. If you’re ready to level up your getaway wardrobe and make every day feel like a highlight reel, check out our curated collection of Vacation Clothes for even more inspo. Trust us, your suitcase (and your Insta feed) will thank you.