Was there a time that the more feathers one had sticking out of one's hat meant one was self-promoting?

Many cultures have used the presence of feathers or other materials attached to one's headpiece to signify importance and/or seniority. The traditional inhabitants of the Americas would be the most famous for their feathers, and seniority in the Roman armies was demonstrated by the length of a soldier's reed(s, which were attached to the front of the helmet).

Placing feathers on one's own head, or adding longer reeds would be a definite no-no, and I doubt it ever happened. The saying is metaphorical and probably derived from this ancient practice.