Typically used in reference to a vehical that exudes massive amounts of swag. A car so incredibly cool that if you look up the word "swag" in the dictionary, you will find a picture of that car. A car that will greatly increase your swag meter just by being near it.
"Wow, look at that car! Whoever drives that swagwagon must be a sexy beast indeed. Oh wait. Thats me."
A swagwagon is like the elite version of an entourage. Unlike an entourage, which can consist of douchebags and chodes, a swagwagon contains only people who radiate vast amounts of swag. Generally, a swagwagon results when someone wielding an epic amount of swag associates and is seen in public with other individuals of similar swag status. Thus, the individual with the epic swag can ride their swagwagon into the most popular clubs, bars, restaurants, and parties generating a lot of positive attention from those not included in the swagwagon.
Guy: Did you hear? James Franco is coming into town to hang out at the most exclusive bars and clubs.
Girl: Yeah, I heard he was coming with Brad Pitt, Johnny Depp, and Gerard Butler: Pretty much the ultimate swagwagon.