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Swag as slang-

Swag, slang originating in the early 1800s for stolen goods or booty; possibly carried by a swagman

Swag, slang originating from the Scottish slang word "swagger" which was a description of the way some Scots walk (in a swaying motion). The word was altered in the English language to mean "the way one presents oneself".

Swag, promotional items given away at trade fairs and events

The phrase "He/She has swag." only makes literary sense if taken as follows: "He/She has (a way to present oneself as an individual)."

Other uses-

Swag Stick, a short cane carried by a military officer.

Sources: Websters Dictionary and Wikipedia.
1: "That man's got some serious swagger!"

2: "Don't point it out! Maybe he has a gimp leg or something."

1: "Or he's Scottish?"

2: "With a peg-leg?"

1: "That must be it."
Swag by Voidn September 7, 2013
Related Words
Contrary to popular belief, SWAG actually stands for Sex With Alex Gaskarth. Alex Gaskarth is the singer of pop punk band All Time Low.
Person 1: Justin Bieber has so much SWAG!

Person 2: Bieber has Sex With Alex Gaskarth? I knew he was gay...
SWAG by alltimeemily January 8, 2012
this shit is swag brov! these are swag ends blud.
swag by MAX MANNN December 27, 2007
the word teenage boys/girls, such as justin bieber. tend to use too often
im too lazy to put a definition, swag
swag by iknoweverythinghaha July 7, 2012
Sex With A Ginger, usually only referring to those who are not truly ginger, but merely have red hair, and thus are lacking freckles, and in possession of one more soul than is allowed for a true ginger.
Holy shit, Karen Gillan is hot. She has me craving SWAG all day!
SWAG by asterisk890 August 19, 2012