You mentioned that Rockport and Cole Haan aren't recommended for well made shoes anymore- what are some high quality brands on the low end of prices (below $200)?

On eBay, Allen Edmonds can be had pretty easily in like new or very good condition for under $200. There are other, higher quality and/or more stylish brands on the ‘Bay, but the sheer volume of AEs all but guarantees that you can find a great pair with a little patience.

If you insist on buying new, Florsheim’s Veblen and Haviland are good options.