Logo on the talis? No problem.
The silky, satin ones that are worn like a scarf? Uh, Houston…
But on the topic of yarmulkas, I did see one that I liked. It was a big capital letter, but done in a Varsity font. Very cool.
Problem is, the kids will no doubt want an initial (like Y for NY Yankees) that does not match his own inital (like Z for Zelig)