So this may change, but here's what I'm going for. There is this very simple tool to make tokens. I don't know the size yet we want, so I'll need to play with it.
http://www.rptools.net/toolbox/token-tool/

I have Character Artist from ProFantasy. It's ok. There are other options. So we will work together to make a representative token. I'm starting with making the best I can... you can add colors as you like. You can use something completely different (Hero builder or something). It should be as close as possible to your character. We're not doing weapons and all of that. We're doing these face tokens because D&D does not have facing. I just want to avoid that as much as possible. I think we'll put good guys in a gold ring and bad guys in a black ring. The background color should be your character's "color" so that remains constant.

I know some of these colors are wrong, but here's an idea of a couple of them. Livid and Renee's tokens are obviously different sizes. We'll see. H is not happy with this Livid, and that's fine. I was just testing the system. And I'm pretty sure that feather needs to be orange and green.

Yea, if an image is going to be there IMO it has to be correct. This is a big part of why I'm so anti-miniature, for instance. I would never allow any of this in my games.

There's also a "hero creator tool" out there that is free, on top of the one Mark is using (which is for pay, but cheap, and I'm sure he'll help you with yours).

I'm also down with us all being kittens or puppies. There should be enough footage of that on the internet. I guess by that standard we could also all be tits.

If you keep whining, I'm going to make you a tiny flaccid dick. It will settle the issue because I'll never have to ask "Who is the tiny flaccid dick?" because I'll know.

If attire changes, tokens can be updated.