Ron Jaworski, formerly of the Phildadelphia Eagles (but we won't hold that against him... too much), the Rams, the Chiefs, and currently of "ESPN Monday Night Football" and "NFL Match-up", had some pretty stereotypical glasses.
See them there? They're rectangular, wire framed, pretty standard. There's something about these glasses, the hair, and the suit that just screams "former-football-player-now-analyst." He just looks so, well, generic. He could be anyone. He could be a slightly-cooler version of John Madden. (I almost called him "Steve Madden" but that's a brand of shoes. A brand of shoes which I doubt he's wearing, but I can't see them in this picture. I bet his are a basic three hole, black lace-up loafer, which is totally fine... as long as they don't suck.)
But Jaworski has moved up in the world with a spanking pair of new glasses! There, sandwiched between some other guys, is Jaworski sporting some geek-chic specs. They've got a nice thick, black band across the top and at the corners, and the bottom of the lenses are unsupported. Even his suit is of better quality and style! Either ESPN hired a good stylist or he started reading GQ. Whichever it is, this a whole new Jaworski.
Just because you played football in the 80's doesn't mean you have to maintain that style. As Wayne from Wayne's World would say "Live in the now!" Which Jaworkski is indeed doing.