Oak Street Bootmakers is a brand that is, of course, known for their boots. It’s right in the name. And, despite not being in the name, they are also consistently listed as one of the “big three” in the Maine handsewn world. However, while they have been making those for as long as they’ve been around, they’ve also been making more substantial, goodyear welted shoes. That includes this – one of the first they launched – the Oak Street Bootmakers Wingtip.
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.