In Australia, swag was the word for a bedroll - a homeless person's belongings rolled up and carried on his back. The person was called a "swagman". It's used in Australia's unofficial national anthem, "Waltzing Matilda".
Your the F*%kin Man, Full of confidence, Style that the ladies drool over, having a monster cock and knowing how to use it, Your name is Chris O'Malley
O'Malley's got so much Swag wherever he goes the girls are drooling over him and guys want to be him. I wish I had his swag.