Sorry I didn't reply! It was nearly midnight here when I was posting before so I went to bed ^^'
I don't find shoes much harder to paint than a flat canvas, but I have had quite a lot of practice. I find it is easier if you use your non-painting hand to "stuff" the shoe so you have a more solid surface to work against, otherwise your shoe will just flop everywhere!
I wouldn't suggest sharpies on acrylic as I said before with my outline issues, it really doesn't work too great.
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