A gentleman-ish thief
Praedis Naïlo is a wood elf rogue played by one of my oldest friends. Because he’s a memeber of one of my parties, I got to know Praedis quite well before ever drawing him, but even so, a wood elf dressed in mostly brown and forest green is a tricky thing to make unique, and … not Legolas. (No shade! my first couple of PCs are woefully generic, although I am very fond of them.)
Happily, my friend gave me a lot of wiggle room with the design, and I used an attractive Native American man for the reference (the photo of whom I’ve lost somewhere - such a shame, he had a great face). I try not to default to Caucasian features unless a character’s description is explicit, since there are plenty of those running around and the visual vocabulary of D&D is better for being broader.
Praedis thieves for the fun, joy, and reputation associated with it, not to become some criminal mastermind, or super-wealthy lord. Or at least, that's what he tells himself, since he generally drinks, carouses, and gambles away his stolen prizes rather than socking them away to save and gather value.
However, every once in a great while, a bauble so catches his eye that he decides to keep it rather than sell it, and those are usually in the form of bracelets, rings, and necklaces. None of which are matching, yet still somehow look "right" when stacked on top of each other. Think Johnny Depp/rocker style.