* Shoes are mostly chosen to work with the pedals (more about this in the Drive chapter). Things to look out for are tighter than normal fit (the foot should not shift), compatibility with the pedal system, and a thick and molded (not flat) sole. Make sure they are not too tight though, or your feet go numb after a long ride. Avoid excessive padding that can take forever to dry after riding in the rain. I prefer long velcro straps because they are easier to open and close, and if they are long enough and tied through a buckle they are no less stable than laces.
One problem with bicycle riding is that the feet get no exercise, which means that it's easy to get cold feet in cold weather. Thin inner socks help somewhat, Goretex outer socks help more (and also keep the feet dry). Boots work best.
* Boots that are pulled over the shoes have two functions: they keep the feet warm, and in wet weather they keep them dry (not completely, especially if holes for pedal cleats are cut into the soles, but dry enough to stay warm). They come in many variants. I have found Carnac and other sewn plastic and lycra types to perform poorly because water gets in through the seams. In my experience Adidas neoprene boots are best by a wide margin, they are tight, have a thick sole to walk on, and stretch somewhat. They'll make your feet go nova when worn in warm places though. Boots work better in the rain if long pant legs are pulled over them because the pant leg otherwise acts like a wick.
* Socks must be close-fitting and have a shaped sewn sole. Don't use sixpack-type socks that can bunch up when riding. As usual, in cold weather it works better to wear an inner and an outer sock; the inner one should be thin and made of cotton, and the outer may be cotton or Goretex. Wool doesn't work as well as cotton or Goretex, and is usually so thick that the shoes are too tight.
See also an article on "Gloves"
