Casual Black Maxi Dresses

Casual black maxi dresses are the ultimate partner-in-crime for every laidback adventure and spontaneous plan. Effortlessly cool, endlessly versatile, and always ready to turn a sidewalk into a runway—these dresses are here to keep your style game strong with zero stress required. Whether you’re brunch-bound, coffee-running, or just vibing with your crew, a casual black maxi dress lets you show up looking put-together without even trying. Throw on your favorite sneakers or some bold accessories and let your confidence do the talking—because when it comes to easy style wins, you just found your new obsession.

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Laid Back Fave Crew Neck Tank Maxi Dress in Black

$34.90

A black rib-knit maxi dress featuring a crew neck and form-hugging, stretchy silhouette for versatile styling.

Windsor Lasting Impression Sheer Mesh Maxi Dress in Black

$38.90

A curve-hugging black maxi dress crafted from partially sheer mesh fabric with a sweetheart neckline.

Windsor All Eyes On You High Slit Maxi Dress in Black

$42.90

A black knit maxi dress featuring a draped cowl neckline, side slit, and flattering ruching.

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Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black

$38.90

(46)

Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules. Fit & FeaturesStretchy ribbed knit fabric, V-neckline, Spaghetti straps, High front slit, Form-hugging fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Perfectly Stylish Sleeveless Ribbed Knit Midi Dress in Black | Size: M | Knit Fabric

Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown

$46.90

(27)

Channel the chic fall vibe in this ditsy floral woven midi dress featuring a sleeveless sweetheart neckline with a ruched bust and tie-front detail, thin tank shoulder straps, and a corset-style bodice. The high waist leads to a flowy A-line silhouette accented with a high-cut front slit. Fit & FeaturesDitsy floral-printed woven fabric, Sweetheart neckline, ruched bust, tie-front detail, underwire bust, Thin tank shoulder straps, Corset-style bodice with piping, high waist seam, Hidden side zipper and hook-eye closure, High front slit, Midi-length A-line fit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Fall Vibe Ditsy Floral Corset Midi Dress in Brown | Size: L | Woven Fabric

Windsor Smooth Talker Strapless Bodycon Midi Dress in Mocha

$33.90

(11)

Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion! Fit & FeaturesRib knit fabric, sewn-in knit lining, moderate stretch, Strapless neckline, Side slit, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Smooth Talker Strapless Bodycon Midi Dress in Mocha | Size: L | Knit Fabric

Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown

$32.90

(10)

The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch. Fit & FeaturesSmooth knit fabric, stretchy knit lining, Sleeveless crew neck, Side ruched seams, Bodycon silhouette, Midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Dinner Downtown Sleeveless Ruched Midi Dress in Brown | Size: XS | Knit Fabric

Pretty Vibes Eyelet Knit Layered Skater Dress in White-2

$32.90

(5)

Show off pretty vibes in this adorable layered skater dress made with breezy eyelet knit fabric. Pair with sneakers for a cute casual look or wedges for a dressier style. Fit & FeaturesStretchy sheer eyelet knit fabric, partial knit lining, Square neckline, Spaghetti straps, Double-layered skater skirt, Short fit-and-flare silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Pretty Vibes Eyelet Knit Layered Skater Dress in White-2 | Size: L | Knit Fabric

Windsor It Girl High Neck Lace Up Maxi Dress in Black

$46.90

(4)

That “did she just walk in?” kind of dress. The bodycon knit dress hugs in all the right places with a lace-up back that does the flirting for you. Fit & FeaturesTexture knit fabric, knit lining, High neckline, Spaghetti straps, Lace-up back, Bodycon fit, maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor It Girl High Neck Lace Up Maxi Dress in Black | Size: M | Knit Fabric

Casually Sultry Strapless Bodycon Midi Dress in Wine

$34.90

(4)

Strut looking casually sultry in this strapless midi dress that accentuates your curves and can easily be dressed up or down! Fit & FeaturesBrushed knit double-lined stretchy knit fabric, Strapless neckline, Side ruched seams, Bodycon silhouette, Midi-length hem, side slit, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Casually Sultry Strapless Bodycon Midi Dress in Wine | Size: S | Knit Fabric

Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown

$45.90

(4)

Own the spotlight on vacation in this midi dress! Featuring a bold halter neckline and an sexy open back, this dress exudes allure, while the bodycon silhouette and slit add a flattering look. Fit & FeaturesSlinky knit fabric, smooth stretchy knit lining, Halter cowl neckline, beaded spaghetti strap tie, Open back with spaghetti strap tie, Bodycon silhouette, Slit accent, midi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Paradise Halter Open Back Slit Midi Dress in Red Brown | Size: L | Knit Fabric

Serving Sleek Square Neck Bodycon Midi Dress in Burgundy

$39.90

(3)

Serve a gorgeous sleek silhouette in this brushed knit midi dress featuring a sleeveless square neckline, thin tank straps, and a midi-length bodycon fit to hug your curves. Style with hoop earrings and stiletto heels. Fit & FeaturesBrushed knit fabric with knit lining, plenty of stretch, Square neckline, Thin tank shoulder straps, Midi-length bodycon silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Serving Sleek Square Neck Bodycon Midi Dress in Burgundy | Size: L | Knit Fabric

Soft Curves Ahead Cap Sleeve Maxi Dress in Black

$39.90

(3)

It’s giving sleek, sculpted, and effortlessly romantic. With a knotted bust, cap sleeves, and a chic back slit, this maxi is your low-key way to steal the spotlight at brunch, cocktail receptions, or date night! Fit & FeaturesSlinky knit fabric, soft knit stretchy lining, Cap sleeves, Sweetheart knotted neckline, Form-hugging silhouette, Center back slit, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Soft Curves Ahead Cap Sleeve Maxi Dress in Black | Size: L | Knit Fabric

Casual Black Maxi Dresses

There’s something quietly powerful about slipping into a casual black maxi dress. It’s the kind of wardrobe move that feels effortless but looks endlessly intentional—like you just know how to make an entrance, even if it’s just at your favorite coffee spot or a last-minute dinner with friends. The beauty of a black long dress casual enough for everyday wear is that it doesn’t demand attention, but it always earns a second glance. Think of it as your style safety net for those days when you want to look put together without trying too hard. Maybe you’re heading out for a winter brunch layered under a cozy cardigan, or maybe you’re running errands with a puffer jacket and chunky boots—the versatility is unmatched. And let’s be real, in December, when the calendar is packed and the weather can’t make up its mind, having a go-to black casual long dress is basically a seasonal superpower. It’s warm enough to layer, sleek enough for impromptu plans, and always ready for a quick dress-up or dress-down moment.

Windsor maxi dresses are made for women who want options without the overwhelm. Whether you’re shopping for yourself or searching for a gift that’s guaranteed to get real-world wear, a windsor black maxi dress is a smart, stylish choice. These dresses suit just about everyone—students juggling classes and coffee runs, professionals who want to look sharp on Zoom and IRL, or anyone who loves a look that transitions from day to night with a switch of shoes. If you’re gifting, it’s the kind of present that feels thoughtful and personal, especially for someone who loves classic pieces with a twist. And if you’re treating yourself, you’ll find that a long black dress casual enough for daily life becomes the backbone of your closet. It’s perfect for those “I have nothing to wear” mornings, those “should I have dressed up more?” evenings, and every spontaneous plan in between. Style it with sneakers and a denim jacket for errands, or swap in heeled boots and statement earrings for a dinner date—this is the definition of low-effort, high-impact dressing.

As you scroll through our curated selection, you’ll notice that each black casual long dress is designed with real life in mind—think soft, wearable fabrics, easy silhouettes, and just enough detail to make you feel special. Maxi lengths add a little drama, but in the most relaxed, wearable way. Black is a year-round staple, but there’s something especially chic about it in winter, when you want to look pulled together without sacrificing comfort. And if you’re feeling inspired to mix things up, don’t miss our lineup of Casual Black Midi Dresses for a fresh take on the classic silhouette. Whether you’re building your closet from scratch or just looking for that one piece to make getting dressed easier, a black long dress casual enough for any agenda is always a good investment. It’s not just about looking great—it’s about feeling ready for whatever the day (or night) throws your way.

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Casual Black Maxi Dresses

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Casual Black Maxi Dresses

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