Midi Skirts and Knee-High Boots Are the Ultimate Wear-Anywhere Fall Combo

Outfits of knee high boots and midi skirts.

I can feel the temperatures dropping—and with them, my hemlines. This season, I’m fully committing to the midi skirt, and not just as a lone hero piece. The real magic is in the power pairing: the skirt + boot combo. It’s a look that’s been championed by Anna Wintour, Gisele Bündchen, and Victoria Beckham—fashion royalty whose style instincts rarely miss. Consider it the holy trinity of fall dressing: chic, practical, and endlessly versatile.

On vacation in London heading for brunch, I reached for an Ulla Johnson skirt and paired it with boots and a cropped sweater from La Ligne—the inspiration for my midi skirt + boot epiphany. (Image credit: Brooke Ely Danielson)

The truth is, this isn’t a new obsession for me. The midi skirt and knee-high boot pairing has long been in my rotation, but right now, it feels like it’s reaching its peak moment. Maybe it’s the sharp tailoring, maybe it’s the luxe leather, or maybe it’s the sheer ease of slipping into something that instantly reads polished. Either way, it’s dominating both my closet and my online shopping carts (hello Net-a-Porter!) as I prep for the season ahead.

I’m breaking down the very best midi skirts and knee-high boots worth investing in right now. Think of it as your shortcut to a uniform that’s equal parts effortless and runway-worthy.

Street Style Inspo

Don't believe me? Look no further than street style, which is as obsessed with the outfit formula as I am.

(Image credit: Launchmetrics)

(Image credit: Launchmetrics)

(Image credit: Launchmetrics)

(Image credit: Launchmetrics)

My Favorite Midi Skirts

Ulla Johnson

Annika High Waist Asymmetric Skirt

Shopbop

A.l.c. Marta Skirt

MAX MARA

Geneve Camel Hair Midi Skirt

Boots to Pair Them With

Shopbop

The Attico Lea Boots

Paris Texas

Knee-High Boots in Soft Off-Black Suede Leather

PARIS TEXAS

Lavinia Snake-Effect Leather Knee-Boots