Urban Dictionary:
1. SWAG
The most used word in the whole ******* universe. Douche bags use it, your kids use it, your mail man uses it, and your ******* dog uses it. If you got swag, you generally wear those ***** hats side way, and your ass hanging out like a ******* goof cause your pants are half way down your white ass legs. To break down the word, it means (Secretly We Are Gay). It is also a word that means to represent yourself/ the way you represent yourself, baggy clothes, ***** hats, small penis and basically a way to say your afraid to come out of the closet.
Assface Magee: I got so much swag
Darrel: You got so much **** in your ass
Assface Magee: **** you, SWAG
Ah, so that is what SWAG means. I have never heard the word used around here.