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What Shoes to Wear with Midi Skirts – The 4 Best Options

What Shoes to Wear with Midi Skirts – The 4 Best Options

Midi skirts are great! They expose a little, but not too much, they are wearable on almost any occasion, and they fit many, many body types and shapes.

So yes, they are great, but it is also a bit difficult to find the right shoe that goes with your midi skirt.

Therefore, we are going to look at some options, and we will answer the question:

What shoes to wear with midi skirts? And we will find the best shoes to wear.

From strappy sandals to kitten heels over combat boots up to block heels, a midi skirt gives a lot of options when it comes to footwear.

However, there are some shoes that are more flattering and some that are a bit more challenging to combine with a midi skirt.

What Shoes to Wear with Midi Skirts

One of the safest options to wear with a midi skirt is pointed-toe low-cut shoes. If stilettos or pointed flats is completely up to you. The pointed toe helps to elongate the leg. But you can also wear knee-high boots or combat boots with your midi skirt. Just check the length of the skirt, you want to have enough space between the skirt and the shoes so that your leg is not visually cut off.

Midi Skirts – What to Know about this Style

What Shoes to Wear with Midi Skirts
Midi skirts are elegant and can be worn in summer and winter.

A midi skirt is any

A midi skirt is any skirt with a length from around two inches below the knee up to one inch above the ankle.

The skirt comes in all shapes and varieties, such as pleated skirts, pencil skirts, A-Line skirts, or raffled-hem skirts.

Each type will also affect what kind of shoes you can wear with them, depending on the volume of the skirt.

For example, a pencil skirt with combat boots can be a bit too heavy, while a pleated skirt with combat boots might be a good option.

Often it is hard to find the perfect shoe for a midi skirt, as the skirt divides the lower body part and therefore tends to make you look shorter.

So it visually draws a horizontal line around the calves, which will let you appear to be shorter.

Easy, you might think, I am just wearing heels or low-cut shoes with a midi skirt.

That would be an approach, however, you certainly can wear boots with a midi skirt.

The Perfect Shoes for Midi Skirts

High Heels

Let’s start with the straightforward choice: high heels.

High heels elongate the legs, if you wear nude high heels this effect will be enhanced.

High heels are also a perfect match with midi skirts because they also elongate the part from the calves to the foot.

Remember that the midi skirt divides the leg into two parts, therefore a few inches extra do not bother.

Flat or heeled Sandals

Flat sandals can also be worn with a midi skirt.

The good news is, that since you wear your sandals barefoot, there is no interruption in the lower leg.

Avoid sandals with an ankle strap, as the strap again creates a horizontal line and interrupts the leg.


Wear sneakers with midi skirts!

This casual combination works best with low-cut sneakers.

Choose a sneaker that is not too chunky, and also a rather casual midi skirt.

A chunky sneaker will visually pull you down, especially with a pencil midi skirt. Your bottom half will appear very heavy and chunky. I know that this style was very trendy, but I feel a plain white sneaker such as Adidas’ Samba Sneaker or a Converse Chick Taylor does a better job for this outfit.

If you decide to wear a rather short midi skirt, you can also wear some socks and plain sneakers with it, or high-top sneakers.

This is an edgy, fun look and is very comfortable to wear. In addition, socks were one of the trend accessories in 2022.

Ankle Boots

Let us look at the most difficult shoe to combine with a midi skirt. In order to wear a midi skirt with ankle boots, the length is key, as well as the shoe length as well as the skirt length.

You want to have enough space between them, therefore choose a midi skirt that ends closer below the knee.

Always keep in mind that every hem and every shoe upper will draw a horizontal line, and your goal is to create a vertical line with almost no interruptions.

So there are different options to keep this vertical line.

Option 1. Wear light-colored or nude ankle boots.

The contrast between your skin tone and the shoe will be less obvious and the eye will see one line.

Option 2. Wear tights in the same color as the shoes.

This will have the effect, that there is no interruption of the colors and the eye will see it as one surface. This helps to elongate the leg visually.

Option 3. Wear a Midi Skirt with a front or side slit.

Thanks to the slit, your leg is visible and the skirt hem will not draw a horizontal line that much.

Therefore, ankle boots will not shorten the leg.

Mid-Calf and Knee-High Boots

This shoe type is a little bit less challenging to combine with a midi skirt.

There is just one rule you need to follow: the skirt should be long enough to cover the upper part of the boots. If this is the case, you are good to go. So knee-high boots are the perfect companion for your midi skirt, especially for colder days. And the good news is: this is also a very sophisticated and chic look to wear to the office. Add a blazer and a waist belt and you have the perfect business outfit.

The Shape of the Shoe Toe matters

We have discussed a few options regarding the shoes to wear with a midi skirt in general.

But also the shape of the shoe can make the difference.

Square Toe Shoes

What Shoes to Wear with Midi Skirts
Square-toe boots are not easy to combine with a midi skirt.

Square-toe shoes are currently on trend, and you see them as loafers, ankle boots, and mid-calf boots.

However, they are not the easiest shoes to wear with a midi skirt.

The reason behind this is that the square creates another horizontal line.

Therefore, the foot appears to be much shorter.

Pointed Toe Shoes

What Shoes to Wear with Midi Skirts
I love wearing cowboy boots with a midi skirt

I love wearing cowboy boots with a midi skirt, I feel like they are one of the best shoes to wear with this style of skirt.

Not only because of the pointed toe, but also because it creates an edgy, yet sophisticated look.

But why are pointed-toe shoes my preferred pair of shoes?

Because pointed Toe shoes are helping to elongate the leg and are therefore the perfect match with a midi skirt.

If you feel that the pointed toe squeezes your feet, go with almond toe shoes instead.

They are less narrow but have the same effect.

No matter if flat pointed shoes or with a heel.

Rounded Toe Shoes

What Shoes to Wear with Midi Skirts

Rounded Toe shoes also have a slightly shorten effect on the legs, but they are still flattering and comfortable.

Therefore, I always wear rounded shoes that come with a heel to balance out this effect.

This does not need to be the four inches heel, but can also be a little kitten heel.

The main point is that the legs get high and the shoes do not make your legs look shorter.

To put it into a nutshell, the best option is a pointed-toe shoe, second a rounded toe, and then a square toe.

The perfect heel with a midi skirt

The four inches high heels might look very flattering but sometimes is not the most comfortable shoe to wear.

Especially if you are planning to wear your midi skirt to the office.

A good combination to wear to the office is a mid-heel shoe with a block heel.

This year chunky block heels with plateau soles were the must wear, however, this style is rather something for an evening event.

Kitten heels are a very feminine and elegant variant of heels. Those heels are perfect also with a pencil skirt in midi length.

What else to know about a midi skirt and how to wear it

Shoes are very important when it comes to creating an outfit.

However, if you feel that the combination of your shoes and skirt is not working for whatever reason, you can try to go monochrome.

Wear a top in the same or very similar color as the skirt.

This will create one surface for the eye and that creates a vertical line.

Go high waist and tuck your shirt in!

Yes, any additional layer will add another cutting line – so tuck your shirt in and you are good to go.

For colder days wear a cropped jacket, and highlight your waistline.


Midi Skirts are never out of fashion, but it can be hard figuring out what shoes are best to wear with these mid-length skirts.

Wear something you feel comfortable in. Sometimes it’s a matter of inches if the shoes and the skirt harmonize.

But besides of all this struggle that can come up when styling a midi skirt, this skirt length is perfect t no matter what age you are, no matter what body shape you have.

But they are also challenging sometimes, so I hope you can excel in your next look with my little guide on midi skirts.

Frequently Asked Questions about a Midi Skirt

Can I wear a midi skirt if I have short legs?

Yes, you can, however, you should choose a skirt, that ends just right under your knees. This gives you more wiggle room for the shoes and it also makes sure that your legs are not visually cut shorter.

How long should the coat be when I combine it with a midi skirt?

The coat should either end with the hem of the skirt, or should be longer. Don’t wear a coat, that is shorter than your skirt. The eye will see this as a cutting line and you appear to be shorter than you actually are.