Very astute of you to notice! I'm not sure but it seems to be related to an artist named Dana Atchley, who created various media-aware projects under the name of "Amazing X." He has some connection to the Ant Farm Collective, a 60s/early 70s group known for spectacles like their Cadillac Ranch and Media Burn.
As for the Navy thing, I'm just guessing at this point but maybe it was connected to some Saulsalito houseboat types? If these hip artists wrangled two rowboats it's possible they decided they commanded a "navy." In any case, it's an insider counter culture art thing, more reflective of who Bridges is than who the character of Richard Bone represents. Atchley had connections in Colorado as well as San Francisco and would have been the type of guy to travel in circles where Hunter S Thompson and the like would know about his work.
Bridges likely wore the shirt as an inside joke, sneaking the message past the costume designer since it was vaguely nautical enough for his character, the part time yacht salesman.
Not directly related, but Francis Coppola sported a Media Burn tee on the of Apocalypse Now.
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