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we've tossed the idea around before, but that's about as far as it has gotten. there are a few things in the way that prevent us from doing this, like the need for engineering support and the concern for losing an 'instantly recognizable face' for champions if there's no longer a standard portrait (more of an issue for spectators than players).
it's not outside of the realm of possibility, but i'm not sure that it's something we'd want and it is competing with other cool things we could do.
If it was technically possible, having an option for "Allow in-game icons to use skins" that's off by default would be a good solution.