An adjective meaning cool, freaky, groovy, amazing, or all of the above, depending on the context in which it's used. Although "trippy" is a fairly new word, the root word, "trip," refers to soft psychedelic trips and has been in use since the 60's.
Person 1: "Whoa, dude. Those yellow fractals in the air are pretty trippy..."

Person 2: "Um, I think you've seriously gotta cut the acid. That's the McDonald's sign."
by Idioteque December 12, 2005
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Reminiscent of something one would experience on a trip on a psychedelic substance. acid, shrooms, salvia, maybe even skunk weed (hey you smoke enough of that...). Can be used in reference to sights such as one would see (patterns, fractals, M.C. Escher, Robert Crumb cartoons), music that evokes feelings of trippin', even heady thoughts similar to ones one would think of while tripping.

Ok seriously if you haven't tripped, you haven't tripped and you don't know what it's like. Period. There should be a law against kids throwing the word "trippy" around like candy, except that it's not like millions of americans follow every single law anyway, felonies be damned. Actually I follow the law and I don't smoke marijuana, just clean, healthy tobacco.... Whatever.
Dude: Man, like... why do millions of people follow bullshit religions, when like... don't they know they're just making stuff up in their heads? Like... how could anyone think they talk with Jesus in their heads? That's like schizophrenia... man... I don't get some people.
Girl: you may be zonked on shrooms but I dig what you're saying. That's some trippy stuff

Pink Floyd, The Flaming Lips, Hendrix, all decidedly trippy music

I suppose trippy is a very subjective word

Kid: Man, that Gantz Graf DVD is trippy!
Other guy: Yeah, I kno... wait... since when have you tripped on anything?
Kid: I don't do drugs.
Other guys: ... wtf?
by Dayraven April 27, 2006
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something that stimulates your drug expirience
this music is trippy
by Olaf Dlugosz April 19, 2006
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Mel thought the colours of the wall paper were so "trippy".
by Alias Jay August 27, 2003
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A shorter version of an Italian name. Changed when brought into America. Used to describe kick ass Italian people you know.
Ya Trippi just took on five people and won with his pinky toe.
by Tripp136 July 05, 2010
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