Having a big uniform outsole like that on a lace up looks goofy to me. Something lower profile with a proper heel looks best I think.
I've ordered a pair of TBNY similar to the dress Varvatos from Zappos just to try on....
Scouring for a pair of Derbys to be worn with jeans. I'd prefer a book-like appearance (showing stitch and lace detail with pants), higher quality/structure, a simple classy upper, $200-$400 price range. I already have a pair of boots...