I'm with Josepidal on this one. Sleekness is key if you're going for a dressier look. C&J, RMW, and EG all make great, sleek shoes. Boots are also an excellent option- check out the WAYWT thread for ideas. You could go with a chunkier boot like AE for a more masculine, rugged look or Chelseas for a sleeker, dressier look. I tend to feel exactly the opposite. I think sleeker shoes are only going to work if you hem to the point of zero break, like GS does on some of his looks. If you have any stacking, JL/C&J etc is going to look dainty and out of place. Even without a break, I still think sleeker thin soled shoes look off. Vass U-last with double sole are certainly sleek but look a lot better with jeans IMO.