I compared my chuck taylors to a pair of nike frees and thought the soles were equivalently flexible. Looking ridiculous is a matter of taste, but any plimsoll-inspired sneaker will probably work the same as a nike free. Vans, Chucks, Keds, etc. Even soccer trainers like adidas gazelles have hardly any sole to them. Haven't seen a "dress" shoe with these concepts that didn't look orthopedic, though.

Sanuk sells thin flexible shoes. They are a bit casual, but a few styles are work friendly:

http://www.sanuk.com/products/341027

VivoBarefoot is another alternative, although a bit more expensive:

http://www.terraplana.com/vivobarefoot.php

You know what looks ridiculous? Hobbling because cool looking shoes have smashed your feet and wrecked your knees.

Feelmax makes shoes that look a bit less odd than Vibrams.