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Really a chimera of two existing groups, the prepster is someone most likely raised in the suburbs and very preppy, that moves to a very hipster centered city (Brooklyn, Portland, Austin), and due to scene exposure adopts certain hipster trends whilst retaining the preppy spirit. Specific examples are skinny jeans with boat shoes, or skinny Nantucket red jeans, cardigans, and keds (although arguably of preppy origin, now adopted by the hipster). The prepster has the ability to flow seamlessly between the two scenes, adopting the traditional seersucker and polos while home, and looking very trendy at loft parties in Williamsburg. This emerging scene has been officially typified by Brooks Brothers new Black Sheep line, designed by Thom Browne, and the new J. Crew Men's store being created with help from Jack Spade. The major difference between the prepster and hipster is money and cleanliness. Drug use also shifts from pot to coke.
Taylor: Hey, have you seen my seersucker shorts, I need to go sailing tomorrow with the rents.
Thom: Yeah, they're right next to your skinny jeans from Uniqlo and your really dirty tee shirt.
Taylor: Dope, thanks.
Thom: Dude, you're such a prepster
by ding ding devo July 10, 2008
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2
a mix between preppy and hipster! They buy clothes from urban outfitters, thrift stores, ralph lauren, tommy hillfiger, and j.crew. They warm-hearted and just want the world better dressed!
preppy hipster fashion style awesome prepster
by Sex on the Regular September 29, 2011
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3
a style/way of life mixing preppy and hipster
Maddie was both preppy and a hipster, SHE WAS A PREPSTER
by margoline February 21, 2012
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4
like a hipster, only less dirty
He golfs, pops the (pink) collar, and rows crew. What a prepster
by kelseylo June 21, 2006
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5
This is just another word for a preppy person, but is different from a 'prep'
See prep I have been called this before instead of just a prep.
She's a prepster with her pink collar popped and ribbon watch.
by Jules February 15, 2005
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6
A culturally confused individual. The most common example is a person who wears Abercrombie&Fitch brand clothes, and yet manages to sag their pants, wear their hats sideways and talk ghetto. In essence, a socially awkward tool.
Guy #1: "Ayo! Both my parents are lawyers and we own a huge house, and I'm thirteen, but I'm still hood yo!"
Guy #2: "Oh my God, shut the fuck up. You're not hood, you're just a Prepster."
by Dan Pierce2 October 20, 2009
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7
Kelly you are not a gangster you are a prepster.
by Patrick April 21, 2005
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