This is basically an excuse for me to nerd out about costumes that I've done and hear what you've all done. Also, I don't have any pictures of these anymore unfortunately.
So, for Halloweens in chronological order IIRC:
-Link (age 5)
-Belle (Beauty and the Beast)
-Generic Hippy (Mom picked that one)
-Magus (Chrono Trigger) (age 8 or 9)
-Popoie (Secret of Mana)
-Zelda (I am DEARLY sorry that I don't have any pics of this one; I worked like hell on that costume)
-Radical Edward (Cowboy Bebop)
-Clopin Trouillefou (the Gypsy king from Hunchback of Notre Dame [another costume I worked like hell on])
And then once I met my boyfriend, our first year we were Bertie and Jeeves (Wodehouse's Jeeves and Wooster series) with a twist: I was Jeeves but dressed as Bertie, and he was Bertie dressed as Jeeves.
The second year, we were Gomez and Morticia (I was Morticia).
Haven't done anything since, but those were pretty awesome.