TK: You’ve been shaping how people think about style and culture for a long time—me included. What first pulled you into this world, and why did you start A Continuous Lean?
MW: It started as the same process the readers were going through. I was curious and wanted to learn. I was interested in certain things I didn’t see represented in the media and wanted to explore them. I was working with a Japanese brand and went to Japan in 2005. There were all these magazines completely devoted to niche subjects—an entire issue just about workwear. I remember thinking, they have a whole magazine about this, and I can’t get one short chore coat story into GQ.
I loved how those magazines went to factories and really talked about how things were made. I grew up in Ohio; my dad wore hoodies. I knew nothing about clothes. So ACL became me documenting my own process of learning, exploring, and celebrating these things. It was never about saying I was an expert. It was more: I’ve studied this, I find this company compelling, these are good people, this product is interesting, it’s worth taking a look at. I was doing the same thing the reader was doing.
TK: With ACL and Pop-Up Flea, you really seemed to catch a wave. Do you think you were tapping into a curiosity that was already there, or did you help lead that shift?
MW: The one thing I’ve always been good at is recognizing platforms. Back then, blogging was a new platform, and I understood it early. Later, I was also early on Substack. I just had a sense that the platform itself would work.
At the same time, guys were starting to feel more comfortable being into clothes. Before that, everything was framed in this slightly mocking way—metrosexual, man bag, all that language. Historically it was dandy. There was always some term to make men feel weird about caring how they dress.
I was picking a very safe topic: heritage brands and rugged Americana clothing. It was easy to say, I’m into this stuff. So you had good timing, the right message, and an alternative to what men’s magazines were doing. People were ready for something different, and I happened to be there.
TK: Early on you were already writing about authenticity, even before it became a buzzword. How do you think about it now.
MW: A good example is when a classic restaurant like Eisenberg’s changes ownership. A new group comes in, rebrands it, updates the menu, and suddenly it’s a cool new place operating in the shell of an old one. There’s a lot of buzz because of who’s behind it, and they’re trading on the nostalgia of something that didn’t survive. I struggle with that. I’ve been back to the new version and like it for what it is, but it’s still complicated.
On the other side, I love the places and brands that have quietly survived. Red Wing is a good example. They’ve kept making certain boots for a long time. They still have a factory here. Everything in the world is telling them to move production to Indonesia, and they just don’t.
The same goes for restaurants that have been around 100 years. Think about what the last five years alone have been like. For some little place to still be there is incredible. Those are the things I get excited about. My dad would always point out places like that when I was a kid—this place has been here forever, it’s an institution, it’s special. That stuck with me. Now, in any city in America, I can find the old place and be thrilled. Some people need new ‘Austin-level cool’ to enjoy a place. I just need an old sandwich shop.
TK: I’ve always wondered how Red Wing felt during that big wave of attention. They were incredibly cool for a stretch, and then the hype moved on—but they’re still there.
MW: For them, Japan was first. They had a heritage division in Japan before they had one in the U.S. Japan goes through intense phases where something trends very hard. Red Wing can be huge there for a time, then it quiets down and only the most dedicated people are still into it.
Culturally, the Japanese really love provenance. They kept those heritage styles alive. That became a real segment of business for Red Wing. I worked with them for a long time. Eventually, the broader world moved on. The brand still sells plenty of boots, and there are people like me who will always love them. But the attention changes, and it can be hard to downshift after that moment. In many ways, the best approach is to be like Alden and remain basically oblivious.
I also have this funny memory: I grew up on the east side of Cleveland, near a Red Wing work-boot store. That’s where I bought my boots. I went to Japan once and bought a pair of Red Wings they didn’t sell in the U.S. Later I took them back to that shop to get repaired. The guys looked at me like I had two heads. They had no idea what they were. I’m explaining I bought them in Japan, and this blue-collar dude in Ohio is just baffled. They still sent them to the factory, but to me that moment is my life in a nutshell.
TK: You made several trips up to San Francisco to work on your bespoke jacket with us. Had you done bespoke before?
MW: I’ve had jackets made, but nothing on the level of this piece—and not in the U.S. This was new for me. It felt like reaching the major leagues.
I loved the process. Because there was no deadline, there was no stress. I didn’t need it for an event or a date. We could just let it breathe and take the time it needed.
One of my favorite moments was the morning of the final fitting. Ryan came downstairs holding the jacket. It was missing a sleeve. That last sleeve was the final step. The jacket was literally coming from upstairs, not out of a box or a shipment.
That’s the appeal for me—this old-school, hand-made, very tangible process. It felt special to be part of it and then to end up with a piece that’s going to live with me for a long time.
TK: With everything happening in your life this year, how did this experience play into it?
MW: This has been a strange year. We lived right next to the Palisades fire and were affected severely. All of my possessions were touched by that. My wife said the experience taught her that material things don’t matter. I realized the opposite: my material things do matter to me.
Not all of them—if I lose a pair of Levi’s, I can buy three new pairs. But there are pieces that carry more weight because of the process behind them. That jacket is one of those things. It holds all this association with San Francisco, with you, with Ryan, with the whole Tailors’ Keep crew. It’s not the most important thing in my life—it’s not my kid—but for a garment, it does a lot of work in the happiness category.
TK: I get that. I’ve got pieces from friends early in their careers. The brand may have changed or stopped, but I still have something from that moment.
MW: Exactly. If you’re a considered consumer, you end up with things tied to people and phases of their lives. Maybe it’s a small brand that doesn’t make it, or a friend who goes on to work somewhere bigger and stops making their own stuff. You still have a piece from that time. If you care about how you buy things, a lot of what you own becomes sentimental.
TK: Tailors’ Keep is marking ten years this year, and we’re thinking about what to change and what not to change. You’ve spent years looking at heritage brands. What do the ones that endure have in common?
MW: The biggest thing is knowing what you like doing, what your customers like, and not chasing after some imagined audience. People should be able to look at Tailors’ Keep and quickly understand what’s good about it and how it fits into their life.
Things get tricky when you work in reverse and try to do things so people will like them or understand them. Sometimes people just aren’t the right customer. If someone can’t look at Tailors’ Keep and see what’s there, they’re probably not your customer—and that’s okay.
Trying to be something for everyone is usually the enemy of longevity.
TK: We were just talking about handmade buttonholes. Some people see them and say they aren’t machine perfect. For us, that’s the whole point. They’re made by hand. Sometimes that’s when we realize it might not be the right fit.
MW: A lot of people simply haven’t been exposed to that kind of work, so they don’t know what they’re looking at. Once they spend time around it, they start to see it. And when that happens, it all makes sense.
Our Locations
San Francisco
Our San Francisco showrooms are nestled at the crux of an eclectic mixture of Jackson Square, the Financial District, North Beach, and Chinatown.
This showroom is appointment-only.
Palo Alto
Our newest showroom in Palo Alto opened in 2023, and is tucked away at 433 Hamilton Avenue.
This location is appointment-only.