Converse are my favorite -- I just feel so nimble? I use toe clips, and the shoes change with the season:
Converse when it's warm enough for me to bike in shorts
slip-on Keds when it's warm-ish, but I'm still wearing leggings (makes changing at work easier)
LL Bean Bean Boots between 40 and 5 degrees
and Gore-Tex LaCrosse winter boots (that effectively look like Bean Boots) between 5 and -35
I won't ride below that...

Basically, I prefer shoes with rounded toes that fit nice in my toe clips and that I owned before I started riding/didn't have to buy anew...