'These boots are made for walking’, sang Nancy Sinatra back in 1966. Now, that’s all well and good Nancy – that is what they do, after all. But sometimes we look to boots as a more utilitarian alternative to our favourite everyday shoes. It’s something the Americans have known for many years: that a well-crafted boot will work for any situation - not just a stroll in the hills or a wood-chopping session. Amongst some of the best bootmakers we've had the pleasure of coming across is Oak Street Bootmakers of Chicago. Founded by George Vlagos, the workshop seeks to "preserve the heritage of U.S. shoemaking through thoughtfully designed and attentively crafted shoes." George is actually a second-generation cobbler, who spent many of his early years learning the trade as an apprentice to his father, John.
A Walk Down Oak Street with Oak Street Bootmakers

Master Cobbler John Vlagos, father of Oak Street Bootmakers founder George Vlagos.
When George founded Oak Street Bootmakers, he insisted on two things: 1) they all be handcrafted in the United States, and 2) they would be designed for longevity. Both are apparent when handling a pair of their Horween-leather pieces; amongst those the Chukka and Trench shapes, but also moccasins and penny loafers. The supple leather is steam pressured and worked through with the craftsman’s hands, yielding a durable outer – a formula that has little changed for over one-hundred years.
This also makes them incredibly comfortable, considering how rugged and strong they appear. Each pair makes use of replaceable outsoles, a feature normally reserved for more formal footwear – thus ensuring a lifetime of wear.
Oak Street Bootmakers are producing shoes made to work - with the same attention as the more elegant Florentine or Northampton cobblers; perhaps not as formal in their design, but with an equally high-level of craft. As a result, devotees of George’s workshop own shoes that are as fitting in the Nevada Desert (paired with some selvedge denim, perhaps?) as they would be at a function in Williamsburg (ditto on the denim). The result: Serious, strong, and one-hundred percent, proudly American.
Contributor
Chris CotonouPublished
July 2019