Originally Posted by AR_Six
In reality a heel here would throw off the proportions because the jacket is cropped and slim[...] TOJ really wants a flat sole.
Dunno, I think there a few good examples of the dr w/ sleek heeled boots (like these appear to be 1, 2, 3). You're right that a chunky boot would look bad though. Sneakers are fine too, just that those CP's are the only contrasting element in your fit and that throws it off for me too.