This is recently finished commission piece I did for benherrin of his OC and Pinkie Pie roller skating. When I started discussing the project one of the decisions was made was that Ponyvile did not have asphalt-paved roads, so making roller skates that would work for ponies and on Macadam roads was a bit of intellectual challenge. I had an idea in mind of how to do the skates and was very happy when I found photographic examples of 19th Century roller skates that used a similar design idea.
Alright then, I guess this picture is more or less perfect.
Also, ponies are bendy.
I’m not sure if rear hooves work like that.
Looks to me like he’s just pushed off backwards with it like a speed skater. The bar goes in the front of the hoof, so the hoof must be tilted, er, counterclockwise.