Stye: Gift or Curse

Keep it 100: When should you draw the line on your attire? For example, one of my school brothers always wear his pants backwards; he did that so much when he was invited to a suit and tie event, he forgot. And i know it kind of hard and it's your style but draw the line when you wear a chain on your side everywhere (and some people count that as a weapon). Everybody love there style but extra is not always better.