6 Midi Skirt and Boots Outfits That Make Winter Dressing Beyond Easy

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. 

Midi Skirts and Boots: @anoukyve wears suede midi skirt with patent leather boots

Photo:

@anoukyve

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 outfit . 

1. PENCIL SKIRT + PATENT BOOTS

Midi Skirts and Boots: @rosiehw wears pencil skirt with patent leather knee-high boots

Photo:

@rosiehw

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. 

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Of course Max Mara makes the perfect camel jumper.

The suede would add such a next textural contrast with the patent boots. 

2. DENIM MIDI + SUEDE 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. 

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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.

3. METALLIC PLEATS + KNEE-HIGH BOOTS

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.  

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A slim-fit t-shirt would perfectly offset the shimmering skirt. Swap for a black round-neck jumper for colder temperatures.

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.

4. SLIP SKIRT + MID-CALF BOOTS

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. 

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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. 

5. DOUBLE LEATHER

Midi Skirts and Boots: @sylviemus_ wears leather midi skirt with leather boots

Photo:

@sylviemus_ 

Style Notes: A monochromatic outfit that looks super chic, Sylvie's nailed the minimalist's approach to styling a leather midi skirt. 

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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. 

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