When was the last time you heard of a quality footwear company’s arrival prompting phone calls from high-profile media companies like the New York Times? Back in 2010, when Oak Street Bootmakers came onto the scene, that’s exactly what happened.

It came as a shock to George Vlagos and Mike Wilkie. George (Oak Street’s founder and design director) had started the brand originally for a very simple reason: he wanted to make a boot that none of the existing American brands were making. That boot eventually became Oak Street’s Trench Boot.

George Vlagos

George Vlagos

As he pursued his grail, George realized that Oak Street might be able to accomplish an even loftier goal—helping to carry the flickering torch of American footwear manufacturing. Mike (Oak Street’s VP of marketing and merchandising) came onboard quite early on, mainly because he found George’s footwear mission to be so damn compelling.

Mike Wilkie

Mike Wilkie

Nonetheless, they were not prepared for what would unfold. Their entire inventory sold out in a flash. George and Mike quickly realized that they had something really special on their hands.

In our absolutely sprawling conversation below, George and Mike talk about what motivated them to launch Oak Street Bootmakers and reflect on those crazy early days. Additionally, we delve into why they made the big leap into hand-lasting all of their welted footwear; their surprisingly deep and loyal following of customers; FX’s hit show The Bear and its connection to George’s Chicago-based clothing shop Independence; a brief story about Usher; and much, much more.

Let’s start all the way back at the beginning. George, how did your experience of growing up in a family that worked in shoe repair lead you to eventually launching Oak Street Bootmakers?

George Vlagos: My dad owns a shoe repair [shop]. He’s a Greek immigrant who has a fourth-grade education. When his family came to the US, there was basically no other option for him other than to work with his hands. For me, growing up, spending time at the shop was a very natural thing. When I was really little, if it was summer and there was nobody able to take care of me that day, my mom, who also works at the shoe repair, would bring me to the shop. Spending time there, sitting on my dad’s lap at the sewing machine, that’s just something that becomes part of you, you know? I remember that rhythm of my dad’s foot on the old Singer sewing machine.

Essentially, I inadvertently learned the ins and outs of shoes. As my dad and my mom would talk over things when I was really little—I wasn’t intentionally listening—but I would overhear things like, “Oh, look at this, another pair of Allen Edmonds that needs new lining at the heel.” Or “The cork on the inside of this shoe is completely rotted out.” Then slowly you learn, well, why does it need new lining at the heel? Why do things like that happen? So, all of that was something that I was interested in, and then in high school, that’s when I really started working there.

John Vlagos

John Vlagos, George’s father

What did they have you doing when you were in high school?

George Vlagos: I would remove soles, often leather soles, and then essentially I’d get it all ready for my dad. Cut all the stitches off the sole, use an adhesive remover and pliers to pull it off. Remove all the stitches out of the welt and remove all the cork. Then I would put the new cork in, reset the shank, sand the new sole, glue it on, and then cut off the excess. I did everything other than stitch the new sole on. My dad would run through them and stitch ’em back on.

Did your dad ever let you take a crack at using the stitcher to get the soles on?

George Vlagos: That came later, during college breaks. That’s when he finally trusted me enough to do it. I was probably 19 years old when I first started. We would take shoes that had been left and abandoned that my dad had already put soles on, and resole them to allow me to learn how to use the machine. That’s the hardest part. You can’t do it on a customer pair, you have to find other shoes to resole. You’d burn through material, so we would try and use soles that were lower grade or were excess.

I’m curious about why you chose to launch your own line of shoes, instead of something like going into the repair industry yourself.

George Vlagos: It actually was because I was looking for a pair of boots that I just couldn’t find in the marketplace. Oak Street Bootmakers was founded because I wanted the Trench Boot. Put yourself back into the year 2006. We might like to think in 2006, the internet was exactly the same as it is today—

[Laugh] Yeah.

George Vlagos: It was not, of course. There was no such thing as Googling for whatever Alden Indy Boot and finding tons of examples of it. Even being in Chicagoland, there was no dealer of a lot of high-end footwear. It was a lot of Allen Edmonds. So I wanted the Trench Boot, and I couldn’t find it. I wanted to figure out a way to get that Trench Boot made. Ultimately, I was able to find a factory willing to make a sample for me, a one-off. When I was able to get that first sample made, I realized that there was something there. That kind of gave me the idea to try and start Oak Street Bootmakers.

oak street bootmakers trench boot natural chromexcel

Mike Wilkie: When I first met George, I think I asked him this same question when he told me that he had grown up working with his dad’s shoe repair. The thing that always really stuck out to me, and made me feel really good about George’s intentions, was that he would talk about how as he grew older, he came to really notice this downshift in the quality. George was kind of coming of age in shoe repair as that shift in quality was happening, and as a lot of the shift to offshoring was happening. He was seeing that firsthand.

I think we all feel more comfortable now with what we’re doing and our mission. But at the time, there was a lot of fire in George’s belly, being frustrated about the state of American shoemaking and where it was.

George Vlagos: It shifted from resole jobs to a lot of just re-gluing. I saw my dad’s frustration with that. He was receiving less and less of the shoes that I had been learning on, and he was getting more and more customers asking “can you get me another year out of these” rather than “can you resole these and get me another 10?”

I felt this sadness. Was my dad’s business viable long-term? If people aren’t bringing in shoes for resoling, he can’t survive on re-glue jobs. Then, as Mike mentioned, there was the offshoring that was happening, causing American factories to completely collapse. So I’m in college, seeing these changes happen, and I’m like, what can I do to make good shoes again in America?

Ultimately, it was that one shoe that I wanted that sparked this idea of reigniting a small flame in American manufacturing. Now, 13 years later, we know it actually did work. People want the Trench Boot, and we’re able to make a meaningful enough amount that it employs people. As small of a customer as we are, we’re buying a TON of Horween leather. The web that this all goes across is so, so big, it’s not just about the people that work in the factories making shoes. Like Maine Thread in the state of Maine. That is a small operation, and they’ve been able to hang in there. But if we and a few other people weren’t making however many thousands of pairs of handsewns…that’s what keeps these companies going.

When I launched, “made in USA” was really becoming a thing in menswear. But for me, made in USA was just what I knew fine footwear to be. When I wanted to get this boot made, I could have probably gone and found some bespoke shoemaker in Italy or somewhere. But I wanted this shoe to be made in America, using American-made leather, using an oak-tanned leather sole from the US, one that my dad would be able to resole.

oak street bootmakers factory sole stitching

I think it’s interesting how you initially framed this whole endeavor as something that you wanted for yourself first: just a particular pair of boots. But then it broadened into something more—a way to support American manufacturing and help people like your dad continue to work.

George Vlagos: 100%, yeah. When I wanted this shoe to be made, it had to be something that could be resoled. That was probably the first thing that I told Mike in our very first phone call. We tell people who want their shoes resoled: if you’ve got a local cobbler, support your local guy. If you don’t have somebody, then send them to us for recrafting. It’s about American manufacturing and an extension of that—shoe cobblers in the US.

How did you two meet originally?

George Vlagos: When I had this idea of starting the company, a friend of mine said, “You should just contact the brands that you admire. People love sharing their stories of success, of how they got started.” One of the brands that I emailed was a leather brand called MAKR, and Jason at MAKR reached back out with “Call me.” One of the questions I had was, who do you work with for your branding, your logo, your photography, your website?

At the time, Mike was running an agency that was working with a number of brands, and he had office space with Jason, so Jason put me in touch with Mike. I told him about this idea for a brand, showed him the samples. And I think Mike immediately fell in love with the product.

Mike Wilkie: This was right on the heels of 2008. A lot of people lost their jobs. A lot of other people—young, ambitious people—didn’t like what they saw, and they just left, even if they weren’t fired. There was this whole surge of startups, people who wanted to do their own thing. For me it was kind of a timing thing, just recognizing that opportunity. I had been working in brand marketing for big blue chip brands before this time, and I hated it. I mean, I loved what I did, but I did not like the clients I was working with. It was very frustrating. A lot of them didn’t understand the Internet yet.

But George was doing something really different. It seemed like, on the one hand, a niche thing, but what was unique about it was it spoke to the larger concern that was happening in a way that these other startups didn’t. They were addressing a niche in a way that was interesting, creative, or necessary. But what George was doing, it just kinda tugged on the heartstrings in a way. The state of the industry and everything, but also, George’s personal history and his passion for the story.

George had less money than any of my clients, but he was immediately my number one client [laughs]. We spent hours a day talking and it was just awesome. I immediately dove in, I wanted to learn everything to play catch up on footwear. And like George said, there was no Stitchdown. There was no place where you could go to get a bird’s eye view of it. I was literally going to the library and finding old books on shoe repair. Photocopying important parts to learn vocab words.

So a lot of it was just me talking to George and him telling me things, and from that I would go and learn stuff. There was some of that going the other way too, with me explaining how the brand stuff would work, and how we were going to take this very complex message and distill it down into bite-sized chunks that a lay person who wasn’t into footwear could understand. We said it over and over and over again so that we could just get it into our heads—“Son of a shoemaker, Horween leather, made in America”—so that when people asked us, we’d be prepared with the elevator pitch.

George Vlagos

Mike, what was your understanding about all this stuff before you started talking to George? Had you heard of things like Goodyear welt construction prior to this?

Mike Wilkie: I didn’t know the terms, but my dad was really old fashioned. He always had a pair of Allen Edmonds and a pair of Florsheims. One Color 8, one black, one loafer, one lace-up. That was always how he rolled. Every 15 years or whatever, he’d turn it over and replace one of ’em. But he’d always have two shoes for work in his rotation.

As a kid, I certainly didn’t have the sort of experience that George did, but I grew up watching a guy who shined his shoes every morning before work, who had a strong relationship with his cobbler that was at our local mall here in Tampa—also a Ukrainian guy, which, you know, as soon as I met George’s dad, I saw so much in common between my dad’s cobbler buddy and George’s dad. Both of them are very opinionated, we’ll put it that way [laughs]. So, I knew enough to understand why I should be concerned at that point in that first call with George.

It literally took him about two years to just get a sample made. Again, I didn’t know anything about footwear manufacturing, but I had worked in manufacturing for a good part of my career at that point. It was alarming to me to know that just our sampling capabilities and everything were so insufficient. In other industries, if you need a metal fitting or something, or if you’re making some kind of robotic something-or-other and there’s a special metal part you need—well, you may not be able to make 3 million of ’em by Christmas, but there’s a million CNC factories that can mill you a sample and have it to you this afternoon, and you can keep going on your product development. But the idea of it taking two years to get a sample…

George Vlagos: [Laughs]

It took you two years to get a sample made?

Mike Wilkie: A final sample, to be clear…it wasn’t like it took him two years to find a factory. It took maybe six months for George to get the first finished sample. What took two years was the complete evolution from sampling reproductions of the actual M1905, which is what George originally wanted, to the final production sample based on the M1917 Pershing/Trench Shoes, with elements of the M1905, and a more refined assembly that would be the Oak Street Bootmakers Trench Boot we all know today. The first samples were spot matches for the OG. Over time, George refined it into something far more practical, wearable, comfortable, with many bootmaking advances that evolved long after World War I.

And even when I say “took six months,” most of that was just trying to get old salty factory guys to take him seriously enough to disrupt the line for his samples.

oak street bootmakers trench boot evolution

The evolution of Oak Street’s Trench Boot, written by Mike Wilkie

George Vlagos: Again, the landscape now is so different. There are Instagram brands that pop up several times a year now. Oak Street was, I think, probably the first [high-quality shoe company] that hadn’t been around for a hundred years. I mean, we were nobody, so who in that landscape is going to make a sample for us? It just was unheard of, and especially so in the US. That’s why I was saying, put yourself back around like 2006. Oak Street didn’t launch until 2010, and getting those samples and patterns made took many years before Oak Street actually launched.

That’s crazy. Do you remember what the specs were on that first boot?

George Vlagos: I actually have it about 50 feet away from me here [laughs]. I don’t remember what the leather is, but it’s a brown upper, Goodyear welt, and it’s a little taller than what the final Trench Boot became. And it had a leather sole. I was all about leather soles back then, and I still prefer leather soles to anything.

oak street bootmakers original trench boot

The original Trench Boot sample pair

oak street bootmakers original trench boot

Around that same time is when all the handsewns kind of came together. I met up with a company called Highland Shoe Company in Maine and worked with them. They were making shoes for Polo at the time, and Polo wasn’t a huge customer, so I worked with them and was able to make all the handsewns that we wanted. Highland ultimately went out of business, but we bought all of the assets, all the lasts and dies that go back decades into the Bass and L.L. Bean days. Those are sitting in our archives now.

That’s great that you were able to preserve that piece of shoe history! So, what was it like when you actually launched Oak Street?

Mike Wilkie: It was such a big deal at the time to launch a new footwear brand. We got up a website, and we had a small email list that I had put together—mostly from my contacts, other brands I’d worked with, and contacts George had made. It was really a homespun operation. We sent out that email to, I dunno, probably 200 or 300 people. Within an hour, we got a call from Travel + Leisure.


Mike Wilkie: Yeah. Can you imagine that today? Like, there’s new footwear brands all the time now. They don’t get calls from Travel + Leisure because it’s not really news anymore. And I’m not saying that people aren’t doing interesting things, because they are for sure. But it’s not the sort of news that it was in 2010.

George Vlagos: It was Travel + Leisure, and the New York Times that called that very first day. August 30th, 2010.


George Vlagos: We sold out within 24 hours of everything that had been made. I’ll never forget that day. I was moving. I’m like, who’s gonna order shoes on the very first day Oak Street exists? So I thought it was fine to be moving that day, I don’t need to be at a computer—we’re sending this email to a few hundred people, who is going to hear about this? I remember being with my wife in our old apartment, and we’re moving, and the phone rings, and it’s Travel + Leisure. They wanted to write a story about Oak Street Bootmakers! I remember telling my wife, “Hang on, Travel + Leisure is on the phone!” And she’s like, “You need to get off that phone! The movers are here, we gotta load up the truck!” And then the New York Times called. Then I called Mike, hours later. I don’t know the technicality of exactly why, but we were sold out of shoes, and orders kept coming in. We hadn’t really set a limit.

oak street bootmakers website original front page

The front page of oakstreetbootmakers.com circa September 2010, courtesy of archive.org

Mike Wilkie: When we launched, we thought orders would trickle in, and if a size sold out, we would just leave the next size up available. If somebody placed an order [for an unavailable size], we would just contact them, because we thought there would be maybe one or two of those. The site wasn’t very sophisticated at that point. We didn’t have a way to have backorder delivery times on the site.

Oh boy, I know where this is going.

Mike Wilkie: So basically, we sold out of everything we had, and then we kept selling more and more. We had to email everybody and say, “Hey, sorry, but your order’s gonna have to get tacked onto the second run.” What was crazy is that we found that nobody cared. They were willing to wait. Two weeks became six to eight weeks, became 10 to 12 weeks. My first patch on the website was adding a feature where we could show how long the current backorder time was. That stayed on the site for like two years, because the orders just kept coming, exceeding our capacity to keep up.

George Vlagos: Mike and I are like, oh my God, we’re sold out. Who’s gonna order shoes from a brand-new brand? They’re gonna go to the website, everything’s gonna be sold out. They’re gonna think we never have shoes.

It didn’t matter. The orders just kept coming in. We’d put five Navy Vibram Trail Oxfords in size 10 into production, but then by the time six weeks rolled around, those size 10s not only had been bought, but there were ten more pre-orders for size 10. So we’d be like, alright, in the next batch, we’re gonna make even more. It took a little more than two years to dig out of the backorder/pre-order situation.

Mike Wilkie: It was so bad that first year. We had been invited to participate in Michael Williams’s Pop Up Flea in New York. Our intention was to use the second run from that fall—we would peel off some extra pairs from that run and bring those to New York. But we sold through all that. So we basically had to beg and plead everybody in the factory to put in some extra time to make more so that we would have a run done just for that show in New York. We had them delivered to the hotel, and they weren’t yet boxed or labeled. So we brought a printer, and we were sitting there in the hotel room with a couple hundred pairs of shoes boxing, labeling, and lacing everything in the hotel room. It was absolute chaos like the night before that show.

So yeah, it was crazy back then. It really felt like we were throwing out this Hail Mary pass when we launched the brand, just hoping that there were some people out there that would understand what we were doing and what the purpose of it was. The response was just overwhelming. It literally took us a decade to catch up, to get the supply and demand in balance. And then right when we did, Covid and the supply chain crisis that followed hit, and it caused us an entirely different set of problems to solve. We’re in a pretty good spot now in terms of supply and demand. For the first time in a long time, we’ve had a year where—obviously we have sold out styles and sizes and stuff—but we’ve been able to keep most of our core stuff available at the appropriate seasonal times this year.

oak street bootmakers factory loafer

How have the changes to the American shoemaking landscape impacted Oak Street over the past 13 years? How have you adapted to those changes?

George Vlagos: Well, I guess things haven’t necessarily gotten easier. They’re easier in that we’re established now.

Mike Wilkie: Yeah, I’d say it’s been good and bad. There was a time where we would order something from Horween, and we’d be at the very end of the list and we’d have to wait forever. Now, George can pick up his phone and call Skip [Horween] and toss an idea out his way and see if he’s interested in working with us. We have people coming to us and asking to work with us now, whereas, back in the early days, we’d be lucky to get a call back. Fortunately, George is really assertive in that way. He put in a lot of legwork in the beginning. Like getting brass eyelets—calling 20 different distributors, finding somebody who will sell us 2,000 of them because they’re used to only selling 100,000. We had to kind of weasel our way into some of these big distributors and manufacturers to just give us a sympathy account back then. Eventually we’d talk to somebody who would be like, oh yeah, these guys are doing something cool, we want to sell to them, we want to be a part of this.

So in that sense, it’s easier now because we have people wanting to work with us. We have tanneries developing something interesting, and they might call us first and say, “Hey, we just did something crazy. You guys want to see it, would you be interested in this?” That’s definitely a new thing. On the other hand, you know, the supply chain is just…it’s very different now. Lead times have increased for everything across the board. Minimums have increased across the board.

Was that true for you guys in the years before the pandemic?

Mike Wilkie:  Since the pandemic, everything has increased. Not just the lead times, not just the MOQs [minimum order quantities], but also the costs, and the shipping times, and the shipping costs. Basically everything takes longer and it costs more, and we have to buy more of it. We’ve had to adapt by doing more long-term planning.

In the past, we might say, “Oh, we wanna do this limited edition. We’ll do 60 pairs of this really special boot!” Then we’d be able to order a couple boxes of soles—a local US distributor might have a couple boxes of Dainites sitting around, ready to ship. Nowadays we work with local distributors where we can, but a lot of times now we have to work directly with the manufacturers, we have to order more to meet their MOQs, and we have to wait longer to get ’em. I mean, sometimes we’re lucky if it’s four to six weeks. That would be good for most things.

oak street bootmakers leathers

George Vlagos: We checked in with Vibram yesterday on a big order that we’re waiting on. It was quoted at six weeks, and it’s gonna be longer than that. Things like that disrupt planning immensely. If you’ve got the leather landing at a certain time, you want people to start cutting it and you want everything to move along. Then things like waiting on soles, that stuff happens, and you’re waiting…eight, nine, ten, eleven, twelve weeks for certain components.

Mike Wilkie: It’s the biggest challenge. I think we’ve finally become better equipped and more knowledgeable—and better able to manage it from a cash flow perspective, which is the biggest challenge of any small business. But what George is saying: if you buy 20 grand worth of leather with the expectation that the soles are gonna be delivered at the same time, and the soles take six weeks longer, you’re out that 20 grand for an extra six weeks.

George Vlagos: You’re just sitting on it.

Mike Wilkie: So, that’s huge. We really recognize the importance of cash flow to keeping up with production and being able to grow the business. That’s meant planning further out with the expectation that we’re gonna be sitting on one component or another. Instead of thinking oh, this is gonna be a four-to-six week thing, we go into it expecting it to be a 12-week thing now, and we plan for it as best we can.

Man, having to double the lead times is tough, but it’s good to hear that you guys have adapted. One of the bigger shifts I’ve noticed you guys have taken in the past few years has been moving towards a hand-lasting process for your “everyday” boots and shoes. Could you tell me about why you wanted to make that change?

Mike Wilkie: We didn’t even start out with the intention to hand-last. Frankly if you go back on Reddit there was a time where we had some QC [quality control] issues, and some customer support issues at the same time, which didn’t make it any easier. It was just growing pains, essentially. Our factory wasn’t able to keep up. They were cutting some corners—not intentionally, but just burning the midnight oil and turning out more capacity than they were really capable of. We were really frustrated by the whole thing, and we didn’t really see a way out other than to bring in a new lead to run the Goodyear welt program.

There was a fellow that George had known for a number of years, who had long expressed an interest in working with us, and it always seemed like he was, frankly, a bit out of our pay scale. But we realized that if we were going to continue, we needed to make clear that we didn’t find QC issues to be acceptable either, and we were willing to make a big play and take a big risk in order to address those concerns. And to be clear, we aren’t talking about massive, widespread big issues. We were seeing customers reach out with small issues with an increased frequency, and we didn’t like where it was headed, and we decided to nip it in the bud.

It was at that point that we started working with somebody with, frankly, a higher level of shoemaking experience under his belt. He made samples for us. To this day, my daily beaters are his first Field Boot sample that he did just using some random roughout that he had on hand. He made ’em in my size, not George’s, and George was like, “Okay, you need to put these on right now and tell me how they feel, let me see how they look.” I put ’em on, and as I was lacing ’em up, I remember looking at George and just being like, “Ohhh! Oh man. I can already tell this is going to be great.”

It was amazing. They felt incredible—the fit, the ergonomics. I mean, they even looked a little better, but the pattern and the last were the same. George was like, “I don’t know what he’s doing. He’s just that good, I guess.” So we talked to him, and then it became clear that, oh, because it was just a sample, he wasn’t gonna bother warming up the lasting machine. He had just hand-lasted it. And we’re like, “Oh. Well…can you just do that for all of them?” [Laughs]

So that’s what we did—we decided to find a way to make it work, to not make it just for sampling, but roll it out across the line. I was really adamant about it, not because of any particular personal interest, but just because that sample was made for me, and George hadn’t tried ’em yet. There was a couple months gap before George had a pair in his size to try on. I was, like, Mr. Hand-last. “We gotta do this, man, it feels amazing!” [Laughs]

George Vlagos: Mike was the loudest proponent of hand-last, which annoyed me. I’m like, it’s not possible. These were just hand-lasted because they were a sample.

oak street bootmakers hand lasting

Why did you think that it wasn’t possible? What was the biggest roadblock?

George Vlagos: The amount of time it takes to hand-last one pair.

Mike Wilkie: You’re talking 30 seconds to machine-last, versus an hour or two, depending on the style, to hand-last.

George Vlagos: And the brute strength involved in pulling and tacking the leather. With the trajectory that we were moving toward in terms of how many pairs we were making, I was like, “Oh, Mike, come on, we can’t. Let’s continue doing this the way we always have.” Until I wore a pair too. I immediately realized that you can feel the difference. A hand-lasted pair, it just has…you know, a machine can’t tell how a leather is pulling. A person can.

Right. From what I understand, with a lasting machine, you can input different amounts of pressure and strength that the “fingers” pull with. But there’s no direct human element.

George Vlagos: Yeah, a person can respond with each grab of their pliers. They use their eye to know where it should be, rather than inputting a pressure pull into a machine, which is gonna be the same from right to left, even though the leather’s not gonna be the same from right foot to left foot. You get a better lasted product, which means a more comfortable product, and one that’s going to, more likely than not, respond the same way for the wearer from right shoe to left shoe. The stretch, the way it gives, is gonna be the same from right foot to left foot, which is just something you’ll never get from a machine. And honestly, there’s something about it—it holds onto your foot better.

oak street bootmakers last

Mike Wilkie: You can see it in the pictures, our new photography versus our old photography. You can see that the silhouette better resolves the shape of the last. It looks more like what it’s supposed to look like. In fact, it looks exactly like what it’s supposed to look like. You can superimpose the last on top of the photo, and you can see that it is the exact same shape, whereas a machine-last is more of an approximation.

The difference might be subtle to somebody that isn’t used to it. They may not notice it right away, like in the stark way that I noticed it—having worn a machine-lasted Trench Boots since 2011, and then suddenly putting on a hand-lasted Field Boot, it was just like, whoa! This is incredible! But again, we did this to address other QC concerns, and we wanted to work with higher-grade leathers and do more limited editions and be more creative. That’s kind of what all this was born out of was, you know, just implementing a higher level of shoemaking across the board.

It’s really become a cornerstone of what sets us apart from a value perspective. It took us a couple years to figure out a way to make it sustainable, but this year we’ve released a limited edition at least every two weeks for the entire year. We’re starting to see the benefits of the investment that we’ve made in upgrading the level of shoemaking.

George Vlagos: And, we haven’t announced it, but all of our Goodyear welt [footwear] are now hand-lasted.

That’s excellent. I know you had already been offering hand-lasted footwear for the limited editions for a while. When did that start?

Mike Wilkie: 2020. We kind of started the transition with the sampling and stuff in 2019, but 2020 is when we relaunched the Lakeshore Boot, and that was fully hand-lasted. We also made some tweaks to the [Lakeshore] last; we’ve also made some tweaks to the Elston last [used on models like the Field Boot and Trench Boot], in part because of what we saw. There were some issues with it. but we could never really put our fingers on exactly how to address it. But hand-lasting made it clear what to do, because of the higher resolution, if you will, of the silhouette—it allowed us to see what changes needed to be made in the last.

So by 2021, all of our limited editions were hand lasted.

Got it.

Mike Wilkie: Then in 2022, we relaunched our Field Boot with hand-lasting, along with some other improvements. It’s an amazing boot now. I think it’s our staff-favorite for sure. And the Cap-Toe Trench Boot. So now, like George said, everything across the entire collection is hand-lasted. We have not announced it for the core Trench Boot yet because we’re still updating the photography. But that’s gonna be coming this fall, and if you bought a Trench Boot in the last year, it’s been hand-lasted, even if it wasn’t marketed as such.

oak street bootmakers n-1 field shoe natural chromexcel roughout marine field

So, on manufacturing concerns, I feel like there’s one thing I need to bring up. You mentioned people on Reddit getting frustrated about QC, and one thing I was hoping you’d be willing to address is exposed welt stitching, and/or welt puckering. This is a problem you are not alone in having, but I feel like it’s one that Oak Street often gets singled out for. What causes this to happen? And is it something you feel consumers should be concerned about?

Mike Wilkie: I think one of the reasons why an issue like that would maybe come up more for us versus our competitors is because, frankly, we’re a more accessible brand in terms of pricing. We sell more units, and there’s more out there in customers’ hands than boots that cost 30 to 100 percent more. We have sales that are quite attractive, making them accessible to even more people. There’s more of our stuff out there than some of our competitors. I think there might be a perception that some of these things might affect us on a percentage basis more than our competitors, but I don’t really think that’s true.

A lot of things like that are things that we might hear about from aficionados, you know? Stitchdown fans might really notice it, whereas a typical customer would never even notice something like that. And that’s not to say that we have a higher level of tolerance for that sort of thing. I think that our QC tolerances are similar, if not higher than our competitors. We do have to make judgment calls on what meets a QC threshold. Customers might have different expectations sometimes about what that threshold is. But the reality is, with a handmade product, there are always going to be variances in every regard. That’s part of the quirk and charm of buying something handmade.

George Vlagos: I mean, Mike’s hit the nail on the head in terms of just the sheer quantity of our boots out there. And I should highlight that we offer a factory guarantee. If anyone ever does have any sort of concern, it’s always covered. That’s where we also really shine, our customer service.

You mentioned the term “puckering” which refers to…man, 2014, I think? That was literally two pairs of shoes. I have never seen what’s been referred to as puckering outside of those two pairs of shoes. Those were shell cordovan boots that we made for Context Clothing. Those two guys got new pairs of boots and were super happy, but during the time in between receiving their shoes, they were loud and vocal. They have become lifelong Oak Street customers.

And then, exposed stitching…well, yeah, that can happen from the tension. Like we said, every leather is gonna respond differently to tension, which is why we at least hand-last. But, if you’re doing anything beyond that, like bespoke, handwelting is going to be an impossibility for a company like ours to grow and be what we want Oak Street to be. Tension needs to be regularly adjusted, which it is, but you’re gonna have times where there’s exposed welt stitching—very, very rarely. That doesn’t create any sort of long-term issue. We’re ten-plus years into people wearing our boots, and we get more in every day for re-crafting that are ten years old. We would never put something out there that has a quality issue. But again, if anything ever gets past us, that’s why we have our factory guarantee.

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Mike Wilkie: Like I mentioned before, customers sometimes have different expectations than what manufacturing tolerances can allow for. Even in those cases, we honor our factory guarantee. If somebody says, “I’m not happy with how this stitch looks” or whatever, we’ll swap it out for ’em, no questions asked. A lot of times I’ll see somebody make a comment like, “I bought this pair couple years ago and I’m upset that this happened. Is that happening still?” And I’m like, well, why didn’t you tell us? Because even before we made our factory guarantee official and put it on the website, we always offered it.

If there was actually an issue that compromised the wearability, the longevity or the overall integrity of the product, we would always replace it or repair. I would say most of the time there’s an issue, it’s a very simple thing that a local cobbler can fix for five or six bucks. And in those cases, we tell ’em, “Hey, just go to your local cobbler and have ’em snip that extra thread off that you don’t like, and send us the bill and we’ll pay for it.”

If you want to know how the Internet can have a way of amplifying the magnitude and the breadth of these sorts of things…it’s rare that we have more than one or two guarantee requests per month. Hundreds and hundreds of pairs out the door in a month, and we’re talking about a fraction of a percent that have an issue that customers find unacceptable. When that does happen, we repair, replace, or refund, no questions asked.


Mike Wilkie: On any given month, 70 percent, give or take, of our footwear sales go to repeat customers.

70 percent…that’s huge!

Mike Wilkie: Most of our average customers are buying between three and five pairs since we’ve begun tracking this. You wouldn’t see that level of customer satisfaction if there were widespread issues.

Something else I’ll say: our Instagram audience is a drop in the bucket. Most of our customers are between 35 and 45, and they’re not on social media. Somebody told them about us, or they found us through searching. A lot of them found us just looking for made-in-USA footwear and have found that we are among the most affordable still in the game.

We have one fellow in Minnesota, he’s bought over 20 pairs in the last two years. We have another customer in California. He’s a retired highway patrol guy. He’s really into leather goods and stuff, and he’s always neck-and-neck with the Minnesota guy in terms of who’s our top customer. The fellow in California, he calls and places orders over the phone, and then he mails us a check.

Wow. [Laugh]

Mike Wilkie: Even though he’s bought over 20 pairs, you’re not hearing his glowing reviews because he’s not on Styleforum, he’s not on Instagram. Most of our customers are like that.

A lot of our customers are older gentlemen who are former Allen Edmonds or Florsheim customers who just kinda had enough with the quality, and wanted something more akin to what they used to get in the ’80s and ’90s. Some of them are former Alden customers who feel that the calculus in terms of cost for quality no longer makes sense for them.

Now obviously, we wouldn’t be running this limited-edition game if we didn’t have a lot of tuned-in online guys as well. A lot of Stitchdown fans, I imagine…a lot of those guys come from a position of skepticism. Maybe they’ve never bought a pair, or maybe they have a less-than-fantastic experience from back in, say, 2015. Those guys reach out to us before they buy. I would say every week there’s probably one or two—somebody reaches out with a DM on Instagram, “Hey, I’m about to buy my first pair, or my first pair in a long time, and I wanted to ask your opinion about this. What do you think?”

And I’ll talk to some of these guys for hours. Not because I need to make the sale, because frankly, from a numbers perspective, that part of our audience is not significant from a profitability standpoint. It is more significant to us from a reputation standpoint.

A lot of times, I tell these guys, “Look, if you’re skeptical, pull the trigger. We have a guarantee online. But in addition to that, you can consider this a personal guarantee: if you have a problem with them, call headquarters and tell ’em—Mike said if I have a problem with them, that I could send them right back.” That’s how we address a lot of the people whose opinions may be shaped by online discussions or maybe a less-than-great experience in the past. We don’t get many returns in those situations, I’ll tell you that much.

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Gotcha. Well, I think you guys are taking the best approach possible. Now, we’ve talked a lot about the past and present, but let’s talk about the future. Based on everything that you guys have said so far—and I think I know the answer—but would you ever consider making some Oak Street products abroad to keep the business going? Or are you all-in on American manufacturing?

George Vlagos: I don’t think we’ll ever need to manufacture products overseas to keep the business afloat. Now, do we have interest in certain types of footwear that are made overseas? Yeah. Cowboy boots, you know, are often made in other parts of the globe.

An Oak Street cowboy boot would be very interesting.

George Vlagos: It’s something worth thinking about. There are certain products that I think certain parts of the world do the best at manufacturing. But when I fell in love with footwear, I fell in love with American-made footwear, and we’ve made it abundantly clear that Oak Street Bootmakers is handcrafted in USA. That’s where our mission is, and that’s where we see Oak Street’s biggest strengths are, and where our growth is—making shoes in the US.

Mike Wilkie: The reason for manufacturing here, it’s not just because we love American manufacturing, and we love the idea of sustaining the shoemaking industry here, though those are both certainly true. It’s also that the styles we make, they were born here. Those styles came to be only because people needed to wear them, and the people making them were working side by side, in concert with one another. The manufacturing and the style are intrinsically linked.

The styles that we make are born in and of America—its challenges, its goals, its history, the type of jobs and industries that we’ve had. I mean, there wouldn’t have been a Trench Boot if it weren’t for the serendipity of the Goodyear welting machinery just happening to come of age at a time when General Pershing needed 2 million pairs of boots in 12 months. Those things are tied together—the history, the manufacturing, and the style, it’s all one thing. So if we might ever consider making something overseas, it would be a style that has that sort of connection to a different place. And I’m not sure it would be an Oak Street product.

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Okay, this next question I have is a little…I mean, it’s not exactly a shoe-related question, but I’ll try and tie it back. I recall that Independence had shared some stories on Instagram highlighting how some of the clothes that were worn in FX’s show The Bear came from the shop. How did that come about?

George Vlagos: Their costume designer essentially had the idea that she wanted all the clothes that were worn by the characters to actually come from Chicago, from stores where the characters could have shopped. So…[Laughs] she bought tons of white T-shirts before that first season. And a ton of Kapital bandanas. The bandanas were worn by the lead female character, Sydney. There was another character [Ebraheim] who wore an Engineered Garments popover. And like, tons of denim. It was pretty incredible, her selections, and it was awesome that they came back for Season Two.

Season Three hasn’t been officially announced yet as of this conversation [Ed. note: Season Three has been confirmed!]. But, I guess the way I bring this back to footwear is…do you think there’s a good chance we see an Oak Street boot popping up in a scene in The Bear?

George Vlagos: I mean, I’m always on the lookout for that stuff.

I would have to think that with Carmy, the main character, having this interest in high-quality clothing and this huge denim collection…I wouldn’t be surprised if he might get into some nice shoes as well.

George Vlagos: Right, right. So, this is crazy, but there’s this guy that works at our shop. His name’s Icky, he’s a 30-plus-year collector of Levi’s, a massive enthusiast with a wealth of knowledge. He called me and told me, “Hey, there’s this TV show, it’s gonna be filmed in Chicago. I met the costume designer and we just started talking about Levi’s. I was telling her about when Levi’s had to paint the arcuates…” And he goes into this detailed description of this Levi’s conversation he had with her. When Season One, Episode One happened, I got multiple phone calls from Pat and Icky and others here who were like, “You have to watch the first five minutes of The Bear, because it’s exactly what Icky and the costume designer talked about!”

But yeah, of course I would love to see Carmy wearing a Trench Boot or Field Boot, maybe some of the other guys wear mocs. It’s interesting when Oak Streets do appear, sometimes unbeknownst to us, in film or TV.

Has that happened much?

George Vlagos: The first thing I can think of right now was that they were in the background in Girls. They filmed at a store in Brooklyn, and the entire wall behind one of the characters was Oak Streets.

Mike Wilkie: Where you will see a lot of Oak Streets is on stage.

George Vlagos: Our list of musicians is huge. We got a call to make navy blue Trench Boots for Jack White for an upcoming tour where he was gonna be wearing all navy blue, and he’s gotten more pairs since then. There was a musician who passed away somewhat recently named Justin Townes Earle…Justin was a massive collector who became a dear friend of mine. The Avett Brothers are another band that we’ve gotten to know very well.

Mike Wilkie: The Wallflowers, they all have Lakeshore Boots.

George Vlagos: Butch Walker—he’s a well-known writer for tons of bands—we sent a pair to…I’ll never forget the shipping label. The address was “FOO REHEARSAL.” So Dave Grohl got a pair. Just thought that was cool. John Mayer has several pairs. That all began with our indigo Trench Boot.

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The indigo boots! That’s quite a first pair.

George Vlagos: Yeah I mean, he’s big into Kapital and that whole world. Those early pairs were indigo-dyed in Japan. He follows us on Instagram and he’s picked up a handful of pairs. But yeah, the list of musicians goes on and on.

Mike Wilkie: I want to give a shoutout to a local Chicago artist, Nathan Graham. He’s a big fan. He posted this behind-the-scenes photo on Instagram right before he went on stage one time and tagged us—he was wearing his Trench Boots. That was awesome.

Hell yeah.

Mike Wilkie: You’ll actually see a lot of Oak Streets behind the scenes. Anything that we’ve done on a commando sole has piqued the interest of a lot of photographers and filmmakers who work in the field. The Trail Oxford, The Camp Boot.

Ah yeah, I remember talking to you about that before.

Mike Wilkie: I mean, it’s really perfect if you work in the field, because you’ve got that really rugged outdoor sole, but a really lightweight, super-comfortable handsewn moccasin upper. A Field Boot on a commando seems like a great choice too, but it weighs four and a half pounds. If you’re on your feet for seven days in a row, 12 hours a day, doing a shoot in Belize where it’s 105 degrees…maybe a boot of that size and heft isn’t your best play, whereas a Camp Boot weighs half that, and still has that handsewn comfort. It really is a tremendous product for people, especially if you’re working in the heat.

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George Vlagos: But the most famous wearer was early on. Usher bought a pair at this store in Manhattan.

Mike Wilkie: He bought them specifically because he needed something to wear to ring the bell on the New York Stock Exchange. And I wasn’t here to see this, but the story goes: he came into the store, saw the mocs, really liked them. He asked for them in his size. He put ’em on, and then he goes and stands at the mirror, and does some kind of dance-move-twirl thing in front of the mirror. Then he was like, “I’ll take ’em.” [Laughs]

[Laugh] Wild. Okay, the last thing I had wanted to ask you about…Earlier this year, George, you were on the Full Grain Podcast, and one of the things that caught my ear was that you were working on stockpiling a bunch of Horween shell cordovan, and were hoping to release it at some point on some boots. Are there any updates with that?

George Vlagos: No…we do have a stockpile that’s continuing to grow, and it’s going to be something special, but no, no details or release dates or anything like that yet. Samples have been made, but decisions still have to be made…what it’s gonna gonna be, boots or mocs? But nothing yet.

Okay! Well I’m really looking forward to seeing what that all looks like. Was there anything else you guys wanted to add on top of everything we’ve discussed today? We’ve been chatting for…a while!

George Vlagos: [Laughs] Yeah. Both Mike and I like to talk.

Mike Wilkie: I’ll say that the best is yet to come. We’ve got a lot of really big ideas, and there’s no shortage of that. The cordovan is just one example of many irons we’ve got in the fire. We have the benefit now of having matured as a company and solved a lot of the problems that a small business must first solve to be able to really be focused on the future. So, yeah, we’ve got a lot of really big ideas, and some of those things are gonna start bearing fruit in 2024.

Our goal isn’t just about making the best boots, but it’s about making the best boots accessible to as many people as possible. Because we know that not just us, but this whole industry isn’t going to survive unless we introduce it to more people to this world by making the financial calculus make sense. We’re always thinking about ways to make a better product, but also keep the prices as affordable as possible.

One of our big concerns with our more premium limited-editions is how to make sure that we’re not pricing out our most loyal customers who’ve been with us since day one. The prices have…well, let’s put it this way, to the extent that our prices have gone up, it’s been a lot less than the broader inflationary trends in the market. We’ve made some sacrifices in terms of margins, and we’re able to do that because we sell primarily online and because our retail strategy is really focused on working with stores who want something unique for their stores rather than using those stores as a volume channel.

We’ve been able to do that through a lot of hard work. A lot of our innovations aren’t in shoemaking in terms of clever engineering tricks, but in ways to optimize how we order, how we plan, how we set up our production flows, so that we can make sure to maintain the sort of cash flow necessary to continue to offer the best prices in fine footwear.

Fantastic. Well, I think we’ll leave it there, guys. Thank you so much again for taking the time to chat.

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