3. Shotaro Kaneda/Jimmy Sparks
Anime Series: Tetsujin 28/Gigantor
While he's not the only kid on this list, Gigantor's controller was a pioneer when it came to rocking a sportcoat and shorts. Usually accented with a dope tie, he was stunting as early as 1956, where he was often sporting a windowpane check coat in the series.