Anime Series: Dragon Ball Z/Dragon Ball GT

Future Trunks was like, the dude you saw as a kid and thought "holy crap he looks awesome!" And in his time, he did. The middle part, the sword on the back of his awesome leather jacket, and his impratical pointy boots. It was like how every 10-year-old wanted to dress. Then in Dragon Ball GT that version of Trunks wore pleated shorts, a kerchief, and a khaki blazer. Definitely not as badass, but acceptable nonetheless.