How can people make different path tiles and make them work?

[Zero1000]

I seem to suck at making paths with multiple types of a single tile. However I see some people paths also have multiple versions of the same tile, but manage to make the path look naturally placed.

I must ask, how can they make a path like that look so well made?

 

[Spooky.]

Practice and a lot of patience. I personally couldn't deal with trying to understand how to make patterns and all so well. I think part of it is also a lot of understanding of pixel art as well. It's mostly trial and error and seeing what works. I'd never made something like that, but if I were to, I would start by looking at some paths others have made that I like and seeing how they did them and adopt similar methods.