For higher-up dress boots, several variations exist, generally some variation on either the soldier boot or the Balmoral boot. The soldier boot you’d want to look for obviously in a sleek design and in my opinion work best as non-Oxford brogues. The Balmoral boot really only works as an Oxford and in my opinion should be a simple non-brogue wingtip. Traditionally Balmoral boots are made with the upper part a lighter color than the lower part, but unicolor and faded variations can also be found.

As far as wearing a jacket with sneakers go, I’m say veto it. If you try to pull off a casual jacket with handkerchief and nice and polished look but you put on sneakers? Eternal damnation.