craftgrrl | Transfering images to shoes + removing iron on transfers?

Okay, I've perused the shoe-related and transfer paper archives, but didn't see anything mentioning what I'm about to ask.

I have a pair of shoes (like chucks but not - baseball (or is it basket ball? or tennis?) style, canvas things that cost about £3). I'd like to put a few images (Shel Silverstein illustrations) onto them. The only way I could think of was with transfer paper, the kind you print out and iron on. But I was wondering if this is possible? I don't think the shoes have been coated with anything, but how waterproof would a transfer be? Or is there another way anyone'd recommend for getting an image onto a shoe?

Also, I have a tshirt that I transfered an image onto ages ago. I didn't wear it that much, so it's still there but I'd like to get rid of it (which is sort of the anti problem going by the transfer archives). Is this possible/easy? It would pick off, but that'd take forever.

p.s Am new here. Hello.