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.
Shop the Look:
Of course Arket makes the perfect beige jumper.
The suede would add such a next textural contrast with the patent boots.
Such a sleek wardrobe staple.
These are some serious 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.
Shop the Look:
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.
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.
Shop the Look:
Every editor on team WWWUK has this knit.
This is my ideal winter party skirt.
The red breaks up the all black outfit perfectly.
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.
Shop the Look:
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
Style Notes: A monochromatic outfit that looks super chic, Sylvie's nailed the minimalist's approach to styling a leather midi skirt.
Shop the Look:
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 flat boot brings a contemporary touch to this whole look.
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.
Shop the Look:
Such a versatile knit for the colder months.
It's giving Cher Horowitz, but for autumn.
Such an investment but well worth it.
This story was published at an earlier time and has since been updated.
-
If You Want a Chic, Timeless Capsule Wardrobe in 2026, Start With These 7 PiecesFrom v-neck knits to funnel-neck coats.
-
9 Winter Work Outfit Ideas for When You Just Can't Be Bothered to Get DressedFormulas that do the work for you.
-
Elegant Dressers Can't Stop Wearing This Polished Colour This Winter (and It's Not Black, Brown or Cream)It's inherently polished.
-
Fashion Girls Ditched All Other Ankle-Boot Trends for This One Specific Rich-Looking StyleAnd here's how to wear it.
-
Boots, Tights, Dress: Amal’s 3-Piece Winter Outfit Formula Looks Chic Every TimeIt will never let you down.
-
These 2 Winter Wardrobe Staples Are the Keys to One of the Most Elegant Outfit Combos EverPerfect pairings.
-
Every Scandi Fashion Person on My Feed Has Ditched Their Trainers for This Specific Boot TrendInstant elegance.
-
Forget Heels for a Second—These 5 Winter Shoe Trends Are Both Comfy and Chic in Equal MeasureNo blister plasters here.
