The top circumference of your sleek, knee-high boots should be snug around your calves. There shouldn’t be more than a quarter of an inch of space at the top of the boot and that’s pushing it. Wearing long, streamlined boots that don’t fit snuggly against the calf is like wearing a tailored jacket that’s too big on the shoulder. It breaks the look.

It’s a tall order finding a pair of knee-high boots that can be worn both over jeans AND with frocks or skirts. Boots over jeans need to be wider and roomier to comfortably accommodate excess fabric. Some boots inherently have the flexibility to work well in both situations:

  • A buckle to adjust calf width: my flat, black riding boots have a magical buckle that’s very handy.
  • A front lacing style: knee-high boots that lace-up in front (like 20 eyelet Dr Martens) can be adjusted to achieve perfect fit.
  • A slouchy style: slouchy boots are not meant to offer a sleek profile. Their fit is scrunched and roomy all over the leg which makes it work equally well over pants and with skirts.

I see quite a few ill-fitting sleek, knee-high boots around town and it’s a shame because boots are pricey. Please make sure that your boots fit at the calf. It makes all the difference.

'Channing' High-heel Buckle Boot Linus Tall Slouch Rider Boot

The streamlined boots on the left are too loose around the calf and are ill-fitting in my book. The slouchy boots on the right are fine to fit a little wider around the calf area because that’s in keeping with the style.