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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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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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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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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a prepster is a hood version of a prep, its like Prep+ Gangster =PREPSTER!! prepsters are like super prepy while still having their gehtoness but a hipster appeal. their happy and hot!! they want to make the world a better more fashionable place. they shop at pac sun hollister and areopostale as well as hot topic and delihas. they are the like the hottest of the preppy kids and walk around with smiles or other random faces their like more a more normal version of scence kids
prepster kids that always wear pac sun and areopostal or hollister all at the same time.
by logan low March 6, 2009
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A childish, spoiled man between the ages of 18 and 30 who exhibits the following characteristics:
1. uses Axe body spray
2. shops at Hollister, preferably, or at Abercrombie & Fitch. If these are not available in his locale, he will shop at Macy's as a last resort.
3. wears his hair in a "bed head" (messy, uncombed) style.
4. aspires to attend a private college, join a fraternity, and one day live like the losers on the "Friends" TV show.
5. hangs out at Starbucks and the mall.
6. would not be caught dead wearing jeans and a t-shirt.
7. comes from a middle-class/upper middle-class family.
8. will become an accountant or office drone after graduating from college and marry a bitch, but will pretend that he is a wild success.
9. listens to adult contemporary of Top 40 radio.
10. when he turns 40, will complain incessantly about his taxes, his kids, and will wonder where his life went wrong.

Origin: Cleveland OH suburbs.

Distinguished from "preppy" in the sense that a preppy is now considered outdated in some circles, and a prepster is a more derogatory term.
At my high school, all the cool kids are either jocks or prepsters.

or

He must be a prepster. The odor of Axe body spray is overwhelming.

or

Can a guy be both a minority and a prepster? Yes, my best friend is a Jewster. I know a couple of blacksters.
by slickbillie August 16, 2009
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