Mid-calf boots are taller than booties with higher shafts, but not as tall as knee-high boots. Their heights finish just under the calf or half way up the calf. I’ve found that mid-calf boots are the trickiest style of boot to incorporate into outfits because the length can create a leg shorting horizontal line across your calf. Mid-calf boots are especially tricky when they’re flat. If you’re after conventionally flattering proportions, go with a low or mid heel mid-calf boot unless you have a relatively long leg line or wear a column of colour. 

Despite their tricky styling, mid-calf boots are trending and looking particularly fresh this season. And based on what I’ve seen coming down the catwalks, there is no stopping the mid-calf boot trend. Here are four easy ways to style dressy and casual mid-calf boots. 

Over Skinnies

Wearing mid-calf boots over skinny pants or jeans is the easiest way to style them, especially when you create a column of colour like in the outfit on the left. Although the flat boots in the outfit on the right are shown with high-contrast skinnies, creating a low contrast between the jeans and top of the boots will lengthen the leg line. So when in doubt about how to wear mid-calf boots — create a low contrast between the skinnies and the boots.

ISABEL MARANT Arnie Leather BootsJIMMY CHOO Leather Biker Boots

With Short Skirts & Dresses

This combination reminds me of the ‘90s. The shorter length of the skirt or dress lengthens the leg line from the knee upwards, which offsets the leg shortening effect of the mid-calf height. Flat mid-calf boots will work as well with shorter hemlines (knee exposure is key). 

The boots in the outfit on the left create a high contrast on the skin tone, which does shorten the leg line a little. But the heels offset that quite well, as does the short hemline of the dress. The boots on the right are low contrast against the skin tone, which effectively lengthens the leg line.

JIMMY CHOO Dart Buckled Leather Biker BootsCHLOE Python Boots

With Knee-Length Skirts 

This combination gets a little trickier because the longer length of the skirt shortens the leg line from the knee down. There are effective ways to lengthen the vertical line of the outfit if that’s your figure flattery priority. First, choose heeled mid-calf booties. Second, match the colour of the skirt with the colour of the booties, as seen in the outfit on the left. The repetition of the colour creates vertical outfit flow which draws the eye up and down. And third, create a column of colour as seen in the outfit on the right. If the model was wearing black boots instead of dark brown, the repetition of colour would have drawn the eye even more vertically (style tip #2).

CHLOE Leather BootsALEXANDER WANG Gia Stretch-suede Boots

With Midi Skirts & Dresses

This combination is a modern take on the ‘70s. The length of the midi closes the gap between skirt hem and boot top which makes for an interesting look because the boots look like regular knee-high boots when you’re standing still. But you’ll see the tops of the boots when the outfit is in motion. In this case style mid-calf boots the same way you would wear knee-high boots. The higher the heel, the easier it will be to create a longer leg line. 

Tucking the top into the skirt – or wearing a crop top – will lengthen the leg line upward from the knees, as seen in the outfit on the right. Tucking is particularly effective because the boots, skirt and top create a high contrast with each other. The top, skirt and boots in the outfit on the left create a low contrast with each other which offsets some of the volume in both the top and skirt. The high heels are instrumental in creating vertical integrity in that outfit.

LANVIN Tasseled Python BootsVALENTINO Patent-leather Boots

I have a pair of flat, dark brown mid-calf moto boots (a NAS purchase several years ago). They are my go-to boots for bad weather and walks with doggies because they are very robust. I wear them over dark blue skinny jeans or black jeans most of the time to create a longer leg line. But I’ve worn them over white jeans too. I have never worn them with skirts or dresses because that would mean a shorter hemline, which is not my preference.

Do you find mid-calf boots difficult to style? Feel free to ask questions in the comments section if you’re struggling to create proportions that you’re happy with.