most popular in the song "My Jeans" by Jenna Rose
In the song, Rose employs her masterful lyrical abilities, including the phrase "jack my swag," to artfully express her grievances against the jeans-wearing community that is in competition with her. The phrase plays a pivotal role in the striking social commentary that pervades the song.
Fun fact: Jenna Rose is pop star Rebecca Black's younger sister.
That girl wore her jeans like me
I bet she's mad, 'cause I look fab
ha ha ha ha jack my swag
- Jenna Rose in "My Jeans"
A reference to the best line of the song "My Jeans" by Rebecca Black wannabe Jenna Rose
1) to jack something is slang for "to steal."
2) swag is common slang for "stuff we all get." Generally speaking, the big bag of random and mostly useless crap you get at a convention of sorts.
Therefore, "jack my swag" quite literally means to "steal my bag of swag (stuff we all get)"
Though, the unfortunate truth of the matter is, this is what people who don't think about what words coming out of their mouths think means "jack my swagger" or to "steal my style".