Let me be honest. When winter comes around, it doesn’t take long for me to slip into a steady rotation—what some might call a rut—of jeans and jumpers. And while I love the effortlessness of the look, this season I’m determined to do things differently. My first plan of action? Finally figure out how to style midi skirts and boots. Thankfully, a quick scroll on trusty Instagram has delivered plenty of inspiration, courtesy of some of my favourite tastemakers.
From my research, it looks like one of the most fashionably foolproof ways to style a midi skirt is with knee-high boots—which just so happens to be one of the top trending footwear styles of the season. Whether you go patent leather or suede, matching tones or contrasting textures, a knee-high boot gives the perfect amount of elevation, and instantly provides a polished finish for the look.
While knee-high boots and midi skirts can create a beautiful, classic look, there’s plenty of room to go with something a touch bolder. A black boot can let a statement skirt shine, or you can create a really sleek look by doubling up on textures—think a leather skirt with leather boots, as you’ll below. And if knee-high boots just are not your thing, fear not—a mid-calf or ankle boot will serve you just as well. Scroll on to see some of the top looks I’ve found that are destined to become your new go-to winter outfit .
Style Notes: Trust Rosie Huntington-Whiteley to have come up with the perfect balance of polish and effortlessness. Take her fashion cue and balance the formality of a pencil skirt with a slouchy knit and sultry pointed patent boots.
Such a sleek wardrobe staple.
Of course Max Mara makes the perfect camel jumper.
These are some serious boots.
The suede would add such a next textural contrast with the patent boots.
Style Notes: A lesson in making winter tones feel fresh and bright—Annabel shows how to take a white denim midi into winter with the help of heeled suede boots.
The base layer for so many potential looks.
The denim midi continues to be a top trend, and this ecru style looks extra polished.
Pair with black tights for an extended leg illusion.
I love the collar on this double-breasted number.
Style Notes: A perfect winter evening look. I love the way the black leather boots and trench really lets the metallic skirt shine without it looking over-the-top.
A slim-fit t-shirt would perfectly offset the shimmering skirt. Swap for a black round-neck jumper for colder temperatures.
This is my ideal winter party skirt.
Yes, it’s an investment, but a leather trench is a style you’ll turn to for years to come.
This simple, classic boot would complete so many chic looks.
Style Notes: Madelynn always knows how to create that enviably effortless New Yorker look, and this outfit just proves the point. The mid-calf boot shows just a hint of skin, and the floaty blouse really adds to the ethereal effect.
Add a chunky cardigan or heavy wool coat as an extra winter layer.
One of the most useful and versatile skirts you can have in your wardrobe.
I love the slouchy fit of these effortlessly cool boots.
Style Notes: A monochromatic outfit that looks super chic, Sylvie’s nailed the minimalist’s approach to styling a leather midi skirt.
A black crew-neck jumper is a winter must-have.
Perfect for layering under knitwear.
When it comes to leather styles, Mango has some of the best pieces on the high street.
The square toe brings a contemporary touch to this whole look.
This story was published at an earlier time and has since been updated.