Riding boots?

[MacMillan of Rathdown]

While it could be done it would look best with a pair of custom fitted buckle riding boots which are pretty much skin tight.
Like this with hose tops folded over the top...

Actually, those are based on the old US Army m-1940 cavalry boot. They were designed to be an easy on, easy off boot, and to eliminate the need for the Army Quartermaster to maintain a supply of boots for mounted troops with varying calf sizes.

I own several pair and they are great for trekking on horseback. They suck little flat rocks when it comes to walking, as there is little or no flexibility in the ankle/heel.