At 35 it has been some years since I dressed up as anything, although there was a period in my early 30s where some friends and I did the Host a Murder Mystery thing that evolved into Halloween parties. The first year we had a full on Halloween Party I was a modern Big Bad Wolf with face and hair paint, fake nails, but wearing a black silk shirt, white tie, and Angel-esque leather coat. A friend came as Biker Little Red Riding Hood - leather dress an aunt gave her that I talked her into wearing (heh), leatherboots, and a red motorcycle helemt.
The next year I, and my girlfriend (now wife), dressed as demons (a succubus and incubuss to be exact). Mostly dressed all in black with goth poet shirts, spirit gummed horns, face paint, big black feathered wings. She wore a corset, short skirt, and tall boots. Worked very well on natural red head.
And if you think I am going to post pix of either of those events you are saddly mistaken.