When it comes to building out your wardrobe, the first thing you should focus on is the key pieces that you know you’ll wear on repeat. In the winter, this might look like an everyday coat or sweater.

But there are also year-round staples like your go-to pair of jeans or your favorite white tee. Both can be mixed and matched in several ways, creating outfits galore. Chief among the year-round wardrobe staples is a black short skirt. 

“A short black skirt tops the closet must-have list,” says Coco Schiffer, a New York-based celebrity stylist. And for good reason: a simple black skirt pretty much goes with everything. “There are very few pieces that are essentials and I would argue this is one of them,” according to Schiffer.

When something is as multi-functional as a black mini skirt, the styling possibilities are endless. “It’s versatile given the fact it can play the starring role of a look, or blend into the background, depending on the styling,” says Schiffer.

But with so much flexibility comes added decision-making. And after you’ve spent time and effort putting together a great outfit, there’s nothing worse than not knowing what shoes should go with it.

Naturally, footwear tends to be one of the last components of an outfit since you likely wouldn’t put them on until you’re done getting dressed. Since there are so many factors to take into account when choosing a pair—like the season, occasion, and style—we asked Schiffer to help break it all down.

Whether you’re styling a black pleated, bubble, or pencil skirt, we’ll have your feet covered. Below is your guide to the five kinds of shoes to wear with your favorite short black skirts. 

Chunky Loafers

When it comes to the ideal shoe and mini skirt combination, Schiffer says: “The goal is to elongate." That’s why a chunky loafer, which provides some extra heel height, is a no-brainer to go with any black mini skirt.

A pair of studded loafers in the season’s trendiest oxblood hue will add even more dimension to an all-black look. You can opt for a shorter hemline like with this bubble micro mini skirt. Slip on a pair of sheer black tights to keep you warm, while subtly incorporating even more texture. 

With Knee High Boots

One of my personal favorite kinds of black skirts is a pleated mini. Ever since Miu Miu’s viral spring/summer 2022 micro mini skirt runway debut, pleated, Y2K style skirts have been back on the scene in a major way. And since we’re already a few years past the point of it just being a trend, it’s safe to say that pleats are here to stay.

To go with the flowy-er style, Schiffer recommends wearing knee-high boots during the colder months. “I would do something with a heel,” she says. An ivory pointed-toe boot will contrast the rest of your look in all the right ways. 

With Pointed Slingbacks

If you were to examine this season’s biggest trends, I’d put money on the oversized coat. While you can show off the rest of your outfit, a black knit short skirt would be my suggestion for styling. The cozy texture will keep you toasty and comfortable while also being super stylish.

To match this level of sophistication, Schiffer remarked that pointed slingbacks, one of her favorite styles, are “so chic and elevates the short black skirt look.” A slingback pair is a solid investment that you will wear again and again. You can wear them with or without tights and with so many other outfits too. They are absolutely a must!

With Stilettos

You could go so many different ways when it comes to dressing up in a black pencil-style mini skirt. One thing that remains true for footwear—no matter what you wear on top—is to keep sleekness in mind. “For example, if you have a pencil skirt, you won’t want to pair it with a chunky sneaker or loafer because proportionally, that would look off,” Schiffer says. Instead, she recommends wearing a pair of pointed stilettos. In this case, since red and black are the main colors of the overall outfit, keeping shoes minimal in white or black would be ideal. 

With Sandals

The fabric in which a black short skirt is designed can change the vibe entirely. A leather A-line short skirt is no different.

And simply because it comes in a heavier weight fabric like leather, doesn’t mean you can’t wear it with sandals. In fact, if the weather allows it, I’d prefer a strappy leather sandal (rather than a boot or loafer) to soften the look.