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 2022 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.

Shoes to wear with skirts



Of course, there are more viable alternatives for each skirt, and we've charted those below, too, but the four looks highlighted really are the most current and the most fail-safe. See and shop our recommendations on what shoes to wear with different skirts below…

1. Midi Skirt + Chunky Sandals

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 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

Shoes to wear with skirts: midi skirt with chunky black sandals



Keep your look classic with a black-and-white palette. 

An elegant skirt that works with just about any sandals. 

Cotton skirts are ideal for balmy summer days. 

If comfort is what you seek, look no further than Tevas. 

2. Slip Skirt + Trainers

Slip skirts are pretty versatile things, but as they tend to err on the side of fancy thanks to their silken fabrications, we'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

Shoes to wear with skirts: pink slip skirt with sneakers and a tee



Use your trainers to give even the fanciest of skirts an off-duty spin. 

Fashion people have been wearing their Converse on repeat lately. 

shoes to wear with skirts: white slip skirt with sneakers and a slouchy top



Monikh gets the skirt-and-trainer look right by keeping her pieces on the minimal side. 

The fluted hem on this skirt makes for a pretty silhouette. 

Khaki trainers are more versatile than you might think. 

3. Short Skirt + Flat Sandals

It's entirely appropriate to wear heels with short hemlines; we just 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

Shoes to wear with skirts: printed mini skirt with flat strappy sandals


Szymon Brzóska/@thestylestalkercom

Look for tops with volumised sleeves to counter a short pelmet skirt. 

This gives off major "rich and unbothered" vibes. 

Fisherman sandals are still going strong. 

Why not add some prints into the skirt equation? 

Sea always creates great minis for summer. 

The velvet texture on these sandals makes them look so luxe. 

4. Pencil Skirt + Strappy 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. We'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

Shoes to wear with skirts: pencil skirt with strappy stiletto sandals



Pair your pencil skirt with a crop jersey top for a cool  high-low balance. 

Faux-leather textures never fail to look expensive. 

These sandals also come in classic black. 

Shoes to wear with skirts: denim pencil skirt with strappy stiletto sandals



This is a masterclass in how to elevate a denim skirt. 

This midi comes in a broad range of sizes. 

The sandals you'll come to rely on for everything, from drinks out to all-day weddings. 

This post was originally published at an earlier time and has since been updated. Next Up: These Tops Go Nicely With Jeans for Those "What Should I Wear?" Days

Related Stories