For summer, you've got your sockless shoe options for those occasions that you want to look like you put in the time (which should be often). But once the colder months hit, boat shoes with socks are probably something you shouldn't be considering, and only the masterful dressers can successfully pull off the socks with loafers look in a non-dressy outfit.

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.

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