Rider Boot Co. doesn't get the attention they deserve, but if the Richmond, VA boot company keeps producing killer boots like the ones made exclusively for Need Supply, then that may change. The "Ottawa" ($645) is a light, yet durable waterproof boot individually handcrafted with vegetable tanned leather from one of the finest tanneries in Italy. A Vibram rubber sole completes the shoe. The Ottawa is the real deal when it comes to a high-style, high-function boot, so place your order through Need Supply until September 15th to have on your feet by October 31. [Need Supply]