Seven Questions: Oak Street Bootmakers

Photos by Nathan Michael.


It’s hard to believe it’s been less than two years since George Vlagos launched Oak Street Bootmakers. In that short time, his label has accrued an impressive line-up of high profile stockists, developed a fervent, near cult-like fan base, received countless glowing blog and forum mentions, and, sold an absolutely ridiculous amount of shoes. Though rapidly achieved, OSB’s success is still well deserved. Combining classic design, top-notch materials and impeccable construction, Oak Street’s range is an easy one to like. Add to that tasteful branding, and a price-point that’s $20 – $40 less than most comparable brands and that like can quickly turn to love.

This month saw the unveiling of Vlagos’ latest endeavor, Independence, a men’s store featuring only US-made goods. Located in Vlagos’ hometown of Chicago (yes, on Oak Street), and boasting an Americana blogger’s wet dream of a brand list, the store is already creating a stir in the Windy City’s retail scene, and will no doubt be draining many a bank account in the coming months. Vlagos recently took some time out to discuss the power of the internet, lessons from his father, and what to do when you sell out of your first collection in 24 hours. Here’s what he had to say.


Well Spent: Give us the Oak Street Bootmakers origin story.
George Vlagos: From a young age, my father, who is a cobbler, had me work at his shop on weekends. He would stack a huge pile of shoes, and give me the entire day to shine them. It’s funny, my dad was actually trying to intimidate me – to show me that working with your hands is difficult, and that I should focus on education. However, I absolutely fell in love with the job. Before my dad could help it, I had him teaching me how to Goodyear welt boots and completely re-craft a pair of fine shoes.

As the years passed, my dad saw his business change – more shoes were being made from molded rubber, and there was a lack of interest in finely crafted footwear, with natural oak leather soles, and replaceable heels. I decided I wanted to create a brand that would not only produce exclusively in the USA, but also use the best leather in the world from Horween in Chicago, offer the product at a fair price, and make shoes that customers could love for years to come.

With that, Oak Street Bootmakers was born


In many ways, OSB was an overnight success. Were you surprised by how quickly the brand took off?
Oak Street’s overnight success was due in large part to the bloggers who were early adopters of our shoes. They wore them, beat them up, and posted about how much they loved them online. Most importantly though, our customers spread the word and continue to do so! They’ve come back for second, third, and even fourth pairs in different styles.

It’s really incredible to see how much pride people have in wearing our shoes. Knowing they’re designed to last, crafted by hand, and that all of the outsoles are fully re-craftable, our customers feel like they’re in on a secret that not everyone is onto yet! We can’t thank our customers enough for their support.

With that said, we learned so much in those early months after launching online. Most notably, we sold out of all of our inventory within the first 24 hours. While selling out seems like a great problem to have, we’re working with a product that is crafted by hand, and the process can’t be rushed. So, we immediately had to go into a 6 week pre-order system. It took us about a year to dig out of that, because orders just kept flooding in! But, we’re happy to say that we finally have stock, so when a shoe does sell out, there’s often a pair in queue right behind it.


Tell us about Independence.
Independence is our men’s retail shop located on Oak Street in Chicago. Independence only features brands that make their products in America. From denim, to shirts, to a popcorn popper – all of the goods in the shop are branded with those beautiful words, “Made in USA.”


Currently, Independence is the only Chicago stockist of OSB. Does the store have any other exclusive brands?
Not only are we the exclusive brick and mortar in Chicago, I’m also designing exclusive OSB styles just for the shop. Right now we have a natural Chromexcel Vibram trail oxford as well as a peanut suede red brick sole trail oxford. It’s crazy – we’ve only been open a few weeks, but the exclusives have been selling out fast – so we’re restocking them as quickly as we can. For now, we do ship the exclusives to customers who are outside of Chicago and call the shop. With this response though, we might need to release these on the Oak Street website in the future.

Independence is also the exclusive Chicago retailer for so many brands that we love, but weren’t available in Chicago until now. We have Engineered Garments, Post Overalls, Imogene+Willie, Left Field, Makr Carry Goods, deadstock American Optical sunglasses, Velva Sheen, Apolis, Stanley & Sons, Archival Clothing, and Two Feet Ahead among others.


Were you always planning on opening a store?
I always wanted a true home for Oak Street Bootmakers. While the brand is sold at retailers worldwide, we really wanted to be in a shop in the brand’s hometown, and, most importantly, to be located on Oak Street. The store is separate from Oak Street Bootmakers, but since I’m involved with both projects, I’m often at the shop fitting people in OSB shoes.


Last year, you added belts to Oak Street’s product range. Any other non-shoe items coming up in the future?
Shoes are definitely my passion, but I’m always designing other things: leather goods, bags, and even clothing. That said, my focus is definitely on shoes for the foreseeable future. I have a lot of surprises coming with the Oak Street line, and I think people are going to be really excited with our offerings over the next 6 months.


What are your thoughts on Chicago style? How does OSB / Independence fit in?
Chicago doesn’t get the credit it deserves! At our opening party, I had never seen so much selvedge denim being worn in a single place.

A buddy of ours who is the vintage buyer for LVC was hanging out at the shop last week. He pointed out that not only do Chicagoans ‘get it,’ they’re smart consumers too. They’re looking for goods that will last, and they can find that at Independence.


Independence is located at 47 E. Oak St. For those outside of Chicago, the store will be launching an e-commerce site very soon. In the meantime, you can check out the latest Oak Street styles at OSB’s website.

Many thanks to Nathan Michael for the photo help.

  • bunmi oloruntoba

    i like