What is a nice and casual shoe for the colder weather? I was thinking of getting desert boots, but heard they do not fare well in the cold and the rain. I am concerned about buying suede desert boots if they will not be able to handle the rain here in Chicago. Are there any other options for nice looking shoes that are good for the colder weather and the rain?
Actually Chukkas are a perfect choice if you have the time to condition and waterproof them. Chamberlains Leather Milk makes wonderful conditioners for all leather products. Though, a drawback would be the fact that you can't use them on suede, so consider getting leather chukkas. Another good shoe option would be dress boots or even saddle shoes.
Desert Boots would be the worst thing to wear. My default casual shoes are boat shoes, but I think that's a result of sleazing around in the Hamptons when I was a young man. When the snow gets deep and dirty, I wear a pair of LL Bean boots: People in Maine know something about cold weather. Don't buy the hunter boots with the rubber bottoms! They are great for early and late winter, but your feet will freeze in the deepest darkest part of the season.
Leather chukka's, leather Chelsea boots, casual leather derby's...all three styles are available in waxed leather as well.
Military style boots if you are wearing some cargos.
Save the desert boots for the summer. ;)
I have a pair of these and they are great for the cold/wet. Many times my feet might get *too* warm.