There’s one item we see constantly popping up on the runways, in street style looks from fashion capitals around the world, and at all of our favorite stores: the black midi skirt. You’d think the arrival of fall would have everyone reaching exclusively for pants, but the truth is that not even the change in weather is enough to make fashionable women stop wearing the wardrobe staple.
The black midi skirt styles that are trendiest for fall and winter 2026 are able to create a look that’s both interesting and sophisticated in equal measure. On the runway, brands like Akris, Rabane, and Ermanno Scervino have presented striking looks with designs that feature fringe, lace, and sheer details; meanwhile, Jacquemus went with a sleek, straight-cut style. Among street style stars, black skirts are the perfect complement to loose-fitting sweaters and oversized blazers. But there is one point where both aesthetic circles converge: black midi skirts look best with heels.
Pumps, ankle-strap heels, mules, booties, and even mesh styles—heels are the go-to choice to pair with black midi skirts for an elegant look. Luckily, retailers have a variety of styles available that’ll pair well with your black midi skirt as well as the rest of your wardrobe. Keep scrolling for the five midi skirt styles our editors are shopping for fall 2026—and what heels to pair them with.
