n. A jobless person who has access to money — especially a trust fund income — and who affects a laid back, bohemian lifestyle.
Other Forms
The Starbucks on Main is joined to an ice cream place called Cows, and the people-watching is as good as the house blend: There were "trustafarians" (dreadlocks, musty clothes and a few hundred thousand in the bank), ski bums, a couple of women in don't-even-ask-how-much ski sweaters and leather pants, and one older guy reading Stendhal.
—Benedict Carey, “Beyond the Winter Olympics,” Chicago Tribune, February 10, 2002
1992 (earliest)
According to "nachr ov realitees," a bimonthly youth-trend report published in New York, the cha ("very cool") words include: "winded" for hung over; "craftsman" for a complete idiot; and "ass" for awful.

Then there's "Trustafarian," which describes a "guy who has long hair and a trust fund, drives a Saab or Jeep, listens to reggae, and doesn't let a whole lot bother him."
—Phil Rabin & Carolyn Myles, “Washington tourism groups unite in search for advertising agency,” The Washington Times, August 26, 1992
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