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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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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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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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Hi tops tongue out, acid wash tapered leg, short-sleeve button-up print with one to many buttons undone, long crew cut with stiff gel, swatch watch

preppy boy swag, hey!

surf prep

ivy surf
Kelly K. says to her friend Jess S. "Look at that hot guy, he looks like he just walked out of a JC Penney magazine."

Z.M. walks over and says "I noticed you ladies eyeing me, if you must know I only wear Arizona jeans."

He walks away slinging his jean jacket over his shoulder like he just left a Canadian wedding.

Jess S. says "Oh my gosh, he is the preppiest prepster I've ever seen."

Z.M. stops to let out a fart and looks around to see if anybody heard.

The girls, oblivious to his flatulence, blush thinking about how deeply embedded his jeans are into his ass.

e.g. Zack Morris (SBTB) = prepster
by dubedge July 15, 2012
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