As we transition out of sneaker and loafer season, it's time to start thinking about the boots you have in rotation. Sometimes all you need is one good pair, other times it's nice to have a few different pairs for different occasions. To help you on your footwear journey, we've gone ahead and rounded up a list of both classics and fancier options. Ask yourself: will I be bracing the snow the next few months? Or are you one of those Californians who only experiences winter in theory? Do you prefer biker-chic, or Dapper Dan? Whatever your needs may be, we have the boot for you.