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3.
in simplest form: "copy my style"

most popular in the song "My Jeans" by Jenna Rose
ABC, 123, that girl wore her jeans like me. I bet she’s mad cause I look fab Hahahaha, jack my swag. Sticks and stones may break my bones but mine (jeans) look new and hers just look so old.
by Cheesy Wonton April 30, 2011
 
1.
A term coined by the accomplished musician Jenna Rose in her hit song "My Jeans".

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.
ABC, 123
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"
by Trigg got a new blackberry May 01, 2011
 
2.
A term to describe a given situation in which a given person steals someone's "swag", or their trademarked coolness. The term has been made famous by Jenna Rose, a twelve year old skinny white chick, in her infamous song, "My Jeans". In the song, a girl (most likely Hannah Montana, Ashley Tisdale, or Keke Palmer) wore jeans just like Jenna's, to which she responded "jack my swag".
I bet she's mad, cuz' I look fab, haha-ha-ha, jack my swag.
by huneygetsit April 17, 2011
 
4.
To have something about your appearance, style, or persona borrowed or stolen with or without malicious intent by another. This can range from sayings, significant others, or most commonly clothing.

A reference to the best line of the song "My Jeans" by Rebecca Black wannabe Jenna Rose
Ha ha ha ha, Jack my swag
by H, right? April 26, 2011
 
5.
Ok, let's break this one down... The sheer lack of understanding and respect for the English language spreading like a stupid wildfire is making me sick.

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".
For example, this might be used at a comic book convention and some fat sweat kid might exclaim "Hey that guy just jacked my swag!" Or some 13 year old girl with a clear misunderstanding of how the English language works and doesn't understand that you don't just abbreviate words at will, might say "jack my swag" as part of her auto-tuned music video expressing her distaste of other people wearing the same jeans. Clearly her strong sense of entitlement under her rich daddy umbrella is completely warranted and supported.
by Concerned Intellectual July 24, 2011