One who carries or has no swag, or basically is lame
Damn boy your so swagless.
by mr.swagg3.0 April 20, 2009
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of or possessing no dollar-sign WAG, incurable...unfortunate
Ryan: Pat, I hear that girl Kelly is swagless
Pat: I know Ryan, damn shame, damn shame.
by DarkpplSteal March 1, 2011
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1. A term that is used to express the state of one's lack of swag.

2. Usually directed towards immature kids who can't accept the fact that they need to grow up and just idolizes weed, wears expensive brands, obsesses with piercings/tattoos, and boasts about the swagger they never have.

3. The absence of swagfulness
1. Boy: hey girl, whats yo numba?
Chick: fuck off
Boy: fml! WAAAAH! let me blog it on my tumblr!
Friend: wow grow some balls. your swaglessness is hurting my reputation...you know what? im not kicking it with you anymore. pussy.
Boy: WAAAH!

2. Boy: dude i bought my obey cap today at Journeys!

Friend: SWAG!
Friend 2: Swag!
Friend 3: Swaaaag!
Chick: please, you are full of swaglessness
by sbinladen December 9, 2011
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This is what you call a guy who exudes an extreme lack of confidence. Typically these people are extremely indecisive, especially when it comes to women, and constantly worry about crap that doesn't matter at the expense of their roommates or friends. Essentially they are the anti-swag.
Swagless Friend: "Hey man, Lindsey just sent me a text wanting to hang out tonight. What should I send back?

Cool Guy: "I don't know, if you want to hang out with her tell her to come over. Stop being such a Swagless Steven."

or

Swagless Friend: "Do you think my shoes match this cool v-neck I just bought?"

Cool Guy: "How about you stop being such a Swagless Steven, and wear what the f*** you want?"
by therealdeal66 August 28, 2009
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a person that is without swag to an extream extent
kate is a swagless wonder
by call me han solo February 7, 2010
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The opposite of this poster's personality. When an urbandictionary user tries to make up a word to start a new trend, they automatically are annointed with swag juice.
How swagless of you to adhere to maintream music.
by kevinwarerip June 24, 2013
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