Iron Man
The character was created by writer-editor Stan Lee, developed by scripter Larry Lieber, and designed by artists Don Heck and Jack Kirby. He made his first appearance in "Tales of Suspense" issue #39 (March 1963).

Made in 1988. Planet pin #019

Made in 1988. Planet pin #020

Planet pin #149. No date - pin obscures date. I'm guessing around 1988.

Made in 1991. Planet pin #198

Made in 1989. Planet pin #

Made in 1994. Planet pin #123

Made in 1993. Planet pin #266

Made in 1994. Planet pin #M113 Iron Man cutout. Soft enamel type pin sold in a blister pack.

Made in 1993. Planet pin #338. First appeared in Machine Man series 2 #1. Arno Stark was the son of Morgan Stark, Tony Stark's cousin, in the alternate reality of Earth 8410 in the year 2020.

Made in 1994. Planet pin #324