Warning, hard facts incoming.
1- Swagmaster Tobirama Senju, the one and only ain't nobody fuckin' with the blue battle armor white fur combo. I hope I don't need to explain myself.
2- Sasuke, the man with the best tailor in the shinobi world. (Part 1 black suit, Shippuden white robes, Taka sleeveless outfit, and especially the panty dropper Boruto outfit; the 5 Kage and War arc outfits were a crime though, probably because he wanted Karin to gtfo)
3- Naruto . I mean, our orange boi might have no game, but you can't deny he's developed a strong sense of style as he grew up, on top of being one handsome motherfucker (Instantly got that Princess (Shion) more wet than Suigetsu, by just fixing his hair). The red Sage Mode cloak, the 6PSM getup, his outfit in The Last etc...
4- Hanabi Hyuga Criminally underrated, despite being the Kunoichi with the best clothes and hairstyles around. Our girl never fail to disappoint. Finally a Hyuga with some decent clothing tastes. She also probably got Hinata that sexy outfit from The Last, so go Hanabi.
5- Lord Orchi-Jackson. Did you see how good he looked with the Sannin Outfit, back when he was still in Konoha? Authorities probably had to hide all the pretty little kids from him, fearing they'd fall for his intense levels of swag.
Honorable mentions:
Sakura and Ino becoming S Rank Milfs in Boruto, and getting some great looking clothes to cement their status.
Obito with his White Mask/ Blue Robes outfit. That looked cool as shit.
Shikamaru in Boruto. He just looks chill as hell. Temari probably had a hand in it.
Minato and his Adidas like jacket with his fiery Hokages cloak can’t lie my man looked badass
