As much as it's simplified, it looks too plain, like some sort of clipart
image put together and a hammer thrown in.
Using colors and text inside was basically to make it look vintage but since
nobody has done a colored version of what i had in mind, there's no way to
know what that would look like but here's a very rough sketch i did using 3
colors which should give you an idea of how much it stands out and what i
exactly wanted. I just did a rough sampling of the boot alone and the
background to give you guys an idea. Im in no way a digital painter so this
is all i could come up with:
http://nightmoves.fedorapeople.org/images/cobbler-rough.jpg
As for the text inside of the circle, it was to make it look like one of
those old logos with the vintage fonts sort of thing.
Let me know.
Abi