So for fall, your footwear must have is the desert--or Chukka--boot. The option above is Cole Haan, but most stores that sell men's clothing and shoes sell this style of boot: Johnston and Murphy, J.Crew, Aldo, Banana Republic, the works. These can be styled with or without socks, tied allt he way up or a little undone, and they look great under jeans, khakis and most things in between. Like the loafer or boat shoe, these are a great non-dress shoe option that really take your outfit to an "I tried" level that makes you seem much more stylish and put together than a pair of sneakers. Also like the boat shoe and/or loafer in your wardrobe, if you're short on shoe options, go with a brown or possibly gray shade that can look good with many outfits and colors. And get them in the material that is most you--suede, leather, whatever. Once you realize what these can do for your look, you'll be finding ways to wear them with pretty much everything you own.