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Swag is an era and aesthetic that was most popular in the late 2000s and early 2010s. It was popularized and inspired by the song "You're a Jerk" by the New Boy'z, as well as hip hop street fashion.[1]


The Swag aesthetic presumably started in the latter half of the 2000s as a movement within the Hip-Hop subculture and can be attributed to the up and coming artists who shared their music online before quickly catching popularity with celebrities at the time such as Miley Cyrus, The Kardashians, Cher Lloyd, Becky G and Rita Ora.


One of the first songs to first start off the swag era was "You're a Jerk" by the New Boy'z, which had even had it's own dance trend. Throughout the years that the swag aesthetic was popular, there were also some other popular songs associated with the aesthetic, such as:

- Black and Yellow by Wiz Khalifa

- Look At Me Now by Chris Brown


Fashion pieces like graphic tees, skinny jeans, and baseball hats were all popular during the Swag Era.

In particular, brands like Obey, Crooks & Castles, Diamond Supply Co, and apparel for the Chicago bulls were commonly used.[2]

It also is known to have an influence from 90s and late 2000s trends along with a preppy, geeky look.

  • Graphic tees
  • Crotch pants
  • Skinny jeans
  • Flannel
  • Fake glasses
  • Gold chains
  • Headphones, worn on the neck
  • Checkered converse
  • Hoop earrings