One who dresses mismatched, unflattering, or just plain goofy therefore everyone knows this person is trying to make his or her own style but failing miserably at it.
Someone who looks like they got dressed in the dark ran out of the house in whatever they through on without looking into a mirror before stepping into the world.
My god, did you look at Betty this morning? She looks like a Gypsy in a Flash Flood!
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