I am not a huge fan of winter but it does give me an opportunity to wear my extensive collection of boots. The Chelsea Boot has become one of my favorite and go-to boots in my collection. I have 2 dress/water proof in black and brown, 1 black dress, 2 casual pebble grain leather in black and brown, and one sporty in woodbury. I may look to add a few suede pairs this season in navy and gray. Before we get into the "Why", lets go over a brief history of the Chelsea boot.