You cant upload in the torishop>texture and then activate right?
The right format of the head is 128x128. The head ,obviously, need to be the the format type of .tga, .jpeg, and others.
If you have the probem while activating INGAME, you can:
-First, you can do the /dl "playername", both in simgle player and in multiplayer.
-Second you can go in multiplayer and wait until your turn. Normaly, when it's your turn, it's already uploaded.
PS.: Have you downloaded the last toribash update?