Go to the Allen Edmonds store that is right across from the Madison Avenue Brooks Brothers. It is a tiny store, and if any one else is there, half the floor will be covered by boxes, but it is a cool little store and you can go to Brooks Brothers and Paul Stuarts right across the street.
Go to your local department store, like J.C.P. or Macy's and look for shoes that look like the above Bass. Often department stores have semi-decent looking shoes for good prices. You can look for brands like Bass, Nunn Bush or Aldo.
I'm sorry, I don't have any good hotel suggestions, but go to the High Line, definitely worth it. It is really beautiful up there, especially if you go at night. I don't know if there is anything you would want to do in the Chelsea/Meatpacking District area, but the High Line would put you within range of Keste'.