Agree with @jssdc on this one. I like the silhouette of the left shoe much better than the one on the right.
@Ds13, if you have no preference between the two, then go with the round toe as it is more classic.
just to be clear, by round toe you guys mean the one on the right? (as you are looking at the pictures, not my right foot)
Thanks everyone. You guys helped make my decision much easier. The ones I'll be keeping are Peal & Co, the more sleek last that I will be getting rid of are Allen Edmonds.
Edit: So not crazy high quality either way, but since I don't wear black shoes often it won't bother me.