The Most Stylish Shoes To Wear With Your Midi Skirt Looks

The midi skirt offers the perfect in-between. Not too short, not too long, but grazing that sweet spot between the knee and ankle — it's the Goldilocks of skirt lengths. High-waisted styles carve out a classic, cinched silhouette, whilst low-slung versions exude that foxy Y2K nonchalance. The skirt's adaptability is endless, too. A silky satin version works for date night, breezy cotton or linen begs warm weather picnics, and midi skirt suits are a great look for work. The midi plays well with almost any mood, making it a true wardrobe workhorse.

It's little wonder, then, that some of the most consistently stylish celebrities continue to champion the style. Gisele Bündchen, Emrata, and Zendaya have all been spotted out and about in wildly different takes on the look — each a reflection of their personal style and a reminder of the midi's impressive versatility. 

But for all it's chameleon charm, the secret to making the midi skirt really sing lies in what you style it with, starting from the ground up. Get the shoe pairing wrong, and the proportions falter. Get it right, and the entire outfit clicks it into place. To demystify the most flattering shoe-midi skirt combinations, fashion stylist and lifestyle expert Joseph Katz exclusively shared his insights with Women, so you can nail the formula every time.

They might be flat, but there's nothing one dimensional about a ballet shoe, and their hyper-feminine elegance brings a certain je ne sais quoi to any midi look. Ballet flats have made a confident return in 2025, updated with fresh details like "mesh panels, square toes, and delicate embellishments," Katz says.

"They provide the perfect complement to midi skirts," Katz adds, noting that they offer "a timeless yet contemporary finish that enhances rather than competes with your skirt's silhouette." It's true: their low, streamlined profile also elongates the leg without sacrificing the look, according to Katz. 

The fashion stylist recommends C. Paravano's square buckle velvet flats as a go-to for this look. He also singled out the Sophia Belt ballet flats from Repetto, a label that's built a cult following of dancers, fashion insiders, and Pinterest boarders alike. There are many ways to ace the ballet flat revival, but when it comes to styling a midi in particular, these shoes are en pointe.

Nothing elevates an outfit — literally and figuratively — quite like a platform sandal. They channel the kitsch of early-2000s pop culture and the theatrical glamour of the '70s, with just enough refinement to land them on the runways of Miu Miu and beyond. According to Katz, "Platform sandals are a midi skirt's perfect match" because "they give you that extra height without killing your feet after an hour."

The interplay of proportions also really makes the look work. "Their chunky, substantial shape plays off the soft flow of a midi skirt," creating a contrast "that makes the whole look feel balanced and intentional," Katz says. He recommends a playful style from FitFlop, or opting for metallic finishes, like these from Aerosoles, when you want to add a hint of color.

Kitten heels have been edging out sky-high stilettos recently — the latter increasingly relegated to the list of outdated shoe trends you don't want to be caught wearing. Low to the ground but high on refinement, the kitten heel brings just enough lift to keep a midi feeling chic. 

Katz is particularly taken with the mule variation, calling it his go-to styling hack for midi skirts. "They elongate the leg beautifully while keeping comfort front and center," he says, a rare combination of ease and elegance that makes them a standout for day to night transition outfits.

For those looking to experiment, try the sleek, geometric designs Jeffrey Campbell has to offer. Katz also cherry-picked these "fierce little heels" from Femme, in a dark burgundy color that was everywhere in spring 2024. These work especially well if your midi is in a deep chocolate brown shade.

When heels feel like too much and ballet flats feel too prim, a pair of stylish sneakers might just strike the right balance. The perfect pair styled with a midi can ground the look whilst still offering a cool, contemporary edge.

For 2025, Katz advised that "the most fashion-forward approach pairs midi skirts with sleek, minimalist sneakers," like these trendy Puma sneakers, the successor to Adidas Sambas. Stars like Dua Lipa, Emily Ratajkowski, and Jennifer Lawrence have all sported the retro style. If you're drawn to color, Katz suggests Seavees for fun, wearable shades, and namechecks Dolce Vita's cornflower blue pair as an easy way to breathe personality into a neutral midi.