Oak Street Bootmakers

For more than the last decade, the Service Boot has been one of the most popular styles of footwear available. Getting it's name from servicemembers of the military, the Service Boot is a military-inspired piece of footwear at it's core. That being said, over time we've seen changes and improvements that make these boots better for every day life.

When it comes to American-made handsewn footwear, there are really three names that consistently come up: Quoddy, Rancourt, and Oak Street Bootmakers. Over the last few years, each of these brands have grown from relative obscurity to being the faces of this classically American style.

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.

The one question I often get asked that I don’t answer in reviews is how I pick which shoes to wear. How I style them, when I pick one over the other, etc. With 100wears hitting the one-year mark, I thought it might be worth providing a mini update on the current collection from a personal viewpoint.

Oak Street Bootmakers is now one of the most established names in the American-made footwear market. In fact, by late 2018, the brand was so large it was able to save a storied Maine factory that at one time made handsewns for Alden, Red Wing, Sperry, Sabago and others by simply buying it when the previous owners were unable to keep the lights on.