Swagger could mean confidence. Artist T.I. gave some adjectives that defined swagger on a different level so I put into a very nice formula for you.
(Charisma + Confidence + Ambition) x Demeanor = Swagger
Watching this interview will really help you understand the TRUE pursuit of the things we want - women, money, fame, friends, security, etc. - and what it takes to get there. You don't have to go to jail, but you will go through punishing adversity. How you respond will not only determine your true success but also define your character.