Discovering Local Frontiers

Drafting It | George Vlagos of Oak Street Bootmakers

July 10, 2012 Features By Photo by GP

Uncovering inspired products and far-flung adventures are why we get up in the morning. It’s a terrible job — but hey, somebody’s got to do it, right?

All of these things start somewhere, though, and often boil down to one decision from a certain type of individual. The type of person who feels the best way to reach your dreams is to stretch for yourself. For some, it’s about solving a problem. For others, it’s about creating something entirely new. In either situation, the process of fostering an idea into reality is inspiring, if only for the theme all creation stories share. Will is a powerful tool in the hands of those exceptional enough to wield it to their goals.

So partnering with our friends at Amstel Light, we decided to set down the pens and shut the laptops, in exchange for conversation. We wanted to chat with the men behind some of our favorite brands, based in some of America’s greatest cities, to hear about their entrepreneurial frontiers first hand.

Our questions? Many. But as we distilled the days we spent with each of these men into our upcoming series of short films we realized one thing. There’s nothing quite as inspiring, or complex, as starting a company. Introducing our four-part film series: Drafting It.

In our first interview, we sat down with George Vlagos, the founder of Oak Street Bootmakers, which specializes in beautifully handcrafted shoes, made in America. As the son of a cobbler, focused on preserving heritage through design and fine shoemaking, George typifies the renewal in American craftsmanship. As a native son of chicago, George also had plenty to say about the Windy City and its role in his personal story.

Watch his video above and make sure to learn about some of George’s favorite spots in Chicago.

Longman & Eagle

This is my favorite restaurant in the city. Everytime I go there with my wife, we’re blown away by the food. Chef Jared Wentworth’s locally-sourced regional American affair is delicious and is reasonably priced. Both of these values mirror our goals at Oak Street, and in many ways Chef Wentworth and I approach our respective crafts in largely the same way.

2657 North Kedzie Avenue |

The United Center — Home of the Chicago Blackhawks

I grew up playing hockey, and the Chicago Blackhawks are a part of who I am. Watching them on the ice is one of my favorite things to do in the city.

1901 West Madison Street |

The Art Institute of Chicago and the City’s Museum Campus.

This world famous museum holds countless seminal works of art in its collection and is not to be missed if you’ve got a creative itch. I have countless memories of visiting this museum as a kid.

111 South Michigan Avenue |

Wrigley Field — Home of the Chicago Cubs

I love hockey — but Baseball is my true passion. Wrigley field is one of the nations most historic ballparks and going to games there is an incredible experience. Seeing the Cubs break their curse is definitely on my bucket list.

1060 West Addison Street |


Ever since Oak Street Bootmakers launched, we wanted to have a retail presence on the actual Oak Street in Chicago. Independence is the realization of that dream and also serves a venue for a variety of other Made in America brands that I love and admire that were hard to find in the city. Working there on the weekends and helping customers actually try on our shoes is one of the most rewarding parts of my job. The warm reception for our locally born business from the Oak Street board of commerce, which normally deals with global retail corporations, has also been phenomenal.

47 East Oak Street |

Drafting It Series:
Seth Rosen of CustomMade | Todd Carmichael of La Colombe | George Vlagos of Oak Street Bootmakers