I always really like Ace Attorney as an example for good character designs. I think Dick Gumshoe is probably my favorite.
It's pretty easy to infer things from his design. He wears a tie so he should be formal, but the top button not being done shows he can't keep up the facade. The unshaven beard kinda suggests he hasn't been able to rest for a while. The trenchcoat and pencil kinda imply detective. The plaster shows he's both goofy and clumsy as well as hardworking, or willing to take a fall for the job. He may not work as a main character since his design wouldn't work for being iconic, but as a side character I've always really liked his design.
Miles Edgeworth and Phoenix also work as good examples imo.