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.
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
Person 1: yo you got a black n mild
Person 2: nah i don't smoke black n milds those are for fags
Person 1: haha yeah just fucking with you
Dylan Levitt: I have a black n mild
Person 1: wow swagless nigga
Person 2: yeah fuckinn sir stunts a lot
Swagless: The Act Of Having No Swag, People who are not cool have zero Swag and therefore are swagless. All Martha's are swagless, even having zero hidden swag