At one point in our history, trades and traditions were handed down through the family tree. Lawyers bred lawyers, cobblers bred cobblers, and so on. Of course, this system limited the vocational possibilities for younger generations, but it conversely guaranteed a heightened emphasis on quality and expertise regardless of the family legacy.

Yet for better or worse, this heritage has been virtually phased out in America – leaving behind only a select few family businesses that specialize in heirloom trades. Within that already limited category, Oak Street Bootmakers is one of the better success stories. The label was founded on generations of traditional shoemaking knowledge and produces some of the best-crafted shoes on the market. To do so, founder, designer, and master cobbler George Vlagos draws on skills he learned from his father to craft a wide variety of handmade leather shoes ranging from penny loafers to work boots.


Given his insights into the industry, Vlagos ensures that each pair is properly constructed with the best materials available. In addition to being cut and sewn by hand, every shoe is outfitted with replaceable outsoles for added durability. Everything is stitched by hand with waxed thread and finished with Vibram soles/toplifts to ensure a sturdy footing where you meet the road. Additionally, Oak Street Bootmakers sources their leather from the renowned Horween Leather Co., which produces trademark leathers that are coveted by shoemakers all over the globe. (Conveniently, the two companies are only separated by a 40 minute drive – a factor which cuts down on transportation costs and it’s harmful byproducts!)

As a company, Oak Street Bootmakers is dedicated to more than just the art of shoemaking. To ensure that their work remains in tip-top shape, they also produce a number of shoe care products. In addition to natural conditioning oils and cleaning tools, the label also offers custom cedar shoe trees that maintain the shape of the shoe and prevent moisture from accumulating during storage. It’s a pretty passionate endeavor.
Be sure to view some hi-resolution images of their shoes and accessories in the gallery below. You can also view their entire collection and gain insights into their process by visiting the Oak Street Bootmakers website.
As I may very well be in the market, let me know which pair is your favorite!
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- Suede Trail Oxford
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- Brazilian Horsehair Shoe Brush
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- Navy Chromexcel Trail Oxford
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- Navy Hunt Boot Lookbook
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- Aromatic Cedar Shoe Trees
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- Beefroll Penny Loafer