13 Shoes to Wear With Your Favorite Midi Skirts

Nothing says “sharp” like a pair of leopard-print derby shoes. Part collegiate, part cool-girl, this timeless style is a natural match for a midi skirt, especially when you add a pair of crew socks.

A shoe as versatile as the Mary Jane almost always makes the list. This pointed-toe version adds instant sophistication, while the flared block heel and V-cut topline keep it firmly on-trend.

Time and again, western boots have proven a perfect match for skirts. This stunning pair features tulip inlay detailing that’s sure to steal the show. Let it shine with a solid midi skirt, or go for a "more is more" moment with a printed one instead.

You’ll find everyday luxury in these Prada platform loafers. At 3½ inches tall, they instantly elevate a skirt outfit, both literally and figuratively.

Sometimes city weather calls for a weather-resistant pair of shoes, and that’s where these lace-ups come in. Beyond their practicality, they add undeniable edge to any skirted look.

Whether you wear them with tights, socks, or on their own, these woven mules add texture and effortless ease to any midi skirt.

Give your summer midi skirts a fall/winter twist with these olive suede boots. Featuring a pointed square toe, this silhouette revives an iconic ’90s boot style.

Sneakers are certainly welcome with midi skirts. This exclusive On x Shoe Palace “Talavera” style is built on the signature Cloudtilt silhouette, which is sporty yet made for everyday wear.

The T-strap pump lends a quiet, old-Hollywood elegance to a midi skirt, with just enough structure to ground the movement of the fabric.

Warmth and sophistication meet in this shearling-lined penny loafer. With plenty of personality, it’s sure to grab attention, and styled with a denim midi skirt, it adds a cozy, comfortable feel.

These sporty Mary Janes pair a soft blush upper with a rugged black sole, making them an easy way to give a feminine midi skirt a little athletic edge.