All the member icons come from users individual profile. The icons will therefore display whatever image the user has chosen to upload for their profile. If they don't set anything, then their initials are simply displayed.
AFAIK there isn't a way to "override" those images.
I hope this helps!
You can change your image following these instructions:
1. Log in to Trello with the user who's image you want to change
2. Click the orb with the users initials in the top right of the screen.
3. Next, click the "Profile" link in the drop down menu (this will bring up the users profile screen).
4. As you hover over the users initials in the top middle of the profile, a change link will appear. Click that link and it will let you select a photo to use from your computer.
Note: There is also a link to "Change Avatar" under the settings tab. This will achieve the same thing :-)
If you get stuck with my instructions, here is a link to the Trello help page on setting up a users image (here)
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