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A yoloswagger is someone who is a member of the yoloswag scene. The yoloswag scene is similar to other popular unfortunate scenes, such as hipsters, emos, and scenesters. Yoloswaggers in essence are new-age gangbangers with a bit more class. They tend to frequently act calm, perhaps stoned, in order to meet the standards of their fellow yoloswaggers. These people tend to wear clothing brands such as Obey and Supreme, and have occasionally adopted the infamous hipster glasses. They also probably listen to Wiz Khalifa, Drake, and Tyga, but may sometimes indulge in OFWGKTA, too.
The word yoloswagger is derived from the words yolo and swag. The word yolo, interestingly enough, originated from the acronym, YOLO, which stands for "you only live once." Yolo and swag are words that are commonly associated with these types of people.
by The Posh Puppy May 23, 2012