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.
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
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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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.
3. PLEATED SKIRT + OVER THE KNEE BOOTS
Style Notes: A pleated midi skirt with over-the-knee boots creates a chic, balanced silhouette. The flowing pleats contrast with the sleek boots, adding a modern edge. Pair with a fitted knit and structured coat for a polished finish.
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These over the knee boots 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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One of the most useful and versatile skirts you can have in your wardrobe.
5. DOUBLE LEATHER
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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When it comes to leather styles, Mango has some of the best pieces on the high street.
6: CHECK SKIRT + POINTED BOOTS
Style Notes: A check midi skirt and pointed boots offer a stylish mix of pattern and sleekness. The sharp lines of the boots balance the skirt’s bold print. Keep your top simple and add a trench for an effortless, put-together look.
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This story was published at an earlier time and has since been updated.
Jess Kelham-Hohler is a freelance writer, editor and content strategist. She has been a contributor for Who What Wear UK since 2023. Currently based in London following six years in Washington D.C. and New York, she was previously the Digital Editor for Soho House & Co, an international group of private members’ clubs for creatives. She has interviewed a range of artists, creators and more, including Alighieri founder Rosh Mahtani, photographer Misan Harriman and fashion editor Lindsay Peoples Wagner. Today, she writes primarily about fashion, travel and culture for various publications, and has worked as a copywriter and content strategist for brands such as Belstaff, Olivela and Equinox.
- Humaa HussainJunior Branded Content Editor
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