See, my only problem preventing this from being an easy answer is that too many of my men are swinging pendulums between 'objectively coolest guy in the room' and 'shivering wet angry chihuahua everyone is laughing at' because that's just the way they seem to come for me, evidently.

But I'll say in the high swag corner is Sakyo and Kagato (wore their fits well, did it all for their love of the game with no regard for how it affected anyone else, but faced their deaths with grace and a smile)

And in the low tier... Matthew Patel used to wear this crown comfortably but the Netflix series actually bolstered his stats up a LOT so now it's harder to say he's a total loser. Elder Toguro is absolutely a swagless little freak though. That man has nothing.