Like 14th Century turnshoes, boots of the period were pointy, and had no heel.
This is a picture of 14th Century boots
taken from the Manesse manuscript.
My boots are not completely authentic, but they are a pretty good fake. I found a pair of soft top cowboy boots for sale used on eBay. They didn't have any decorative stitching, but they did have an odd alligator pattern stamped into the leather grain in places.
I sanded the grain smooth, and polished them with a low-gloss polish. Then, I took them to a shoe repair shop, and had the rounded cowboy top and heels cut off. There is just a thin heel pad left, because the sole wasn't flat.
I find the cowboy connection to be very interesting. Saddle strings and bolo ties are very much like medieval points. Conchos look and work like medieval belt fittings. Pointy toes are still in fashion. I'm increasingly convinced that 16th Century Spanish colonists left a pocket of medieval culture in the American west which, like the choir robes and votive candles in church, has survived continuously to the present day.