The second concept piece is currently the best, I think. Strange as it sounds, at a first glance Samson's eyes and teeth could pass as a hair-band, which serves to give Filia a more innocent and harmless appearance. I think the fedora is an important part of the design, as it covers the teeth.
In regards to the base design, I would recommend discarding either the waistcoat two-button line, or the suspender straps - the entire point of a waistcoat is to hide bulky-looking belts straps from view. Visually, they go together about as well as sandal-socks.
The overcoat is a good thought, but I think it needs more detail before it can really add to the 'evil' look you're trying to build for Filia. Possibly bulking up on the collar/lapels of the coat and adding a few buttons would make it appear more Capone, less cafone. The right choice of color scheme, should you decide to color it, will help too.
Don't forget to change Filia's shoes in the finished copy. As you've shown Filia, she's wearing a very expensive suit - and her regular brown loafers clash with the new outfit. I'd recommend designing a pair of Oxford black-and-white shoes to help complete the composition.