Knee-High Boots: From Courrèges Go-Go to the Everyday Pair

The first fashion moment for the knee-high boot belongs to Courrèges, whose go-go boots appeared in 1964. In February 1966 Nancy Sinatra released These Boots Are Made for Walkin', and the song gave the idea its swagger. After years of ankle booties and chunky lug soles, the knee-high boot is the elongating, serious option. It makes skirts feel purposeful and turns jeans into an outfit.

The shaft is where most people go wrong. It should hug your calf without pinching, and sit just below the knee. Check the circumference before you buy. Brands measure the calf differently, so check the numbers on Stuart Weitzman, Vince, Dolce Vita and Reformation before you order. Zip the boot all the way up, then sit down. If the top digs into the back of your knee, try another pair.

A block heel of around two inches is the most practical. A slim heel is dressier. A flat riding boot is the easiest to walk in, and a stacked heel feels more 1970s. Look for a rubber sole or add a thin protector for rain. Picture her in a pair of dark brown leather boots, a wool skirt and a camel coat, crossing a street in drizzle. The boots hold their line without trying.

Under a midi skirt, knee-high boots create a seamless line. With a short dress, they can look a bit retro. Over slim trousers, tucked in, they look sharp. In our fashion dreams she wears them with a long cardigan, a scarf and a leather bag, and never thinks about her feet. Black is the safest. Brown leather is warmer, and suede is softer and needs a protective spray before the first rain.

I would skip boots with a shaft that gapes at the calf, since the line looks sloppy. I would skip very shiny patent, which can feel like a costume. And I would skip very high heels if you plan to walk. A good knee-high boot should feel like a part of your legs by the second wear.