Not All Shoes and Skirts Work Together, But These 4 Combinations Are Perfect

I wish I could tell you that skirt-and-shoe pairings are classic and never-changing, but they're not. A lot of the items involved in getting the "right" formulas together will already be sitting in your wardrobe—it's often just a case of seeing what feels most suitable for now. For example, you might have neglected those sporty, chunky sandals you bought for an adventurous holiday, but now they're the most 2021 thing to wear with a midi skirt.

From what works perfectly with a '90s slip on a day-to-day basis to the shoes required to make a pencil skirt look sassy and not like you're heading into a serious, pre-lockdown board meeting, we have a few handy combinations to see you through. We know they work because the team here wear them on the regular, and our wider network of influencers and fashion insiders have also been relying on them.

I remember when midi skirts became popular again around seven years ago. Back then, it was all about wearing them with high heels to balance out the volume. Now we're more than used to the silhouette, so it's only natural that our shoe options have opened up. At the moment, you'll find stylish women making the most of summer's chunky, flat sandal trend and pairing their trusty midis with Tevas, Suicokes or any given pair of slightly clompy open-toe styles.

Other Options: Platform sandals, knee-high boots, trainers, and mid-height heels

Slip skirts are pretty versatile things, but as they tend to err on the side of fancy thanks to their silken fabrications, I'd suggest wearing a pair of casual shoes to balance them out (unless you're heading off for a night on the tiles). So that means trainers are the most comfortable, relaxed and easy-to-find option.

Other Options: Backless mules, flat sandals, strappy heels, and chunky sandals

It's entirely appropriate to wear heels with short hemlines; I just personally feel it's much cooler during the daytime to stick to flats or low heels. Whether ballet pumps (yes, they're back) or simple flat sandals, you'll always feel a bit more laid-back.

Other Options: Loafers, slippers, brogues, trainers, ankle boots, ballet pumps, low-heel courts, party heels

It may have been a while since you last wore a pencil skirt. But the street style set have spoken, and it very much looks like this body-hugging silhouette is coming back in. Whether in sombre colours or rendered in leather and denim, pencil skirts generally tend to look best with heels, but right now, it's specifically about strappy sandals. I'd say that pencils are very tough to pull off with flat shoes or ankle boots, as this can give the illusion of shorter legs.

Other Options: Court shoes, over-the-knee boots, knee-high pull-on boots

This post was originally published at an earlier time and has since been updated.

Next Up: 6 Flat Shoes That Are Almost as Comfortable as Slippers