When does a footwear company go from start up to established brand? Oak Street Bootmakers has only been around since 2010. I bet there are people reading this page who have socks older than this brand. However, when taking a look at the market, there are now countless brands trying to do to Oak Street Bootmakers what they did to Alden and Allen Edmonds. Truman, Grant Stone, Parkhurst, and more all followed the path set forward by Oak Street Bootmakers. I thought it might be worth going back to the genesis of Oak Street Bootmakers, one of their first models – the Trench Boot.