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For Shoe Designer Rob Gregg, There Is No Typical Day

Meet the self-made style man who plans to disrupt a centuries-old industry 

Rob Gregg is something of a modern-day Renaissance man.

A native of California, Gregg landed in New York a few years ago, to chase more than a few dreams. Today, he holds a full-time consulting position by day, but fills his seemingly limitless remaining hours as a dress-shoe designer, GQ Insider, and all-around (and well-dressed) man about town.

Gregg’s passion is his “luxury performance” shoe line called Rob McAllan—an idea that came about after realizing men’s dress shoes haven’t changed much in the past century or two. With a concept and a prototype, he worked doggedly to track down designers, suppliers, and manufacturers to bring the shoes to life.

Amid his jam-packed schedule, we recently caught up with Gregg to discuss life and style—and where the two intersect.

Obviously, there are a lot of dress shoes on the market. How are yours different—and how do you stand out?

The brand is inspiring—taking something that usually blends in and makes a man stand out. The more condensed version? Men’s dress shoes are the only luxury product that people buy and accept discomfort. They have 100- to 200-year-old design standards. And tradition doesn’t necessarily translate to comfort.

When I ask someone to try on a pair, unequivocally, it’s like they opened up their first birthday gift. How does a shoe that looks this good feel this comfortable?

You’re passionate about telling your story. Do you think brand storytelling has become easier, with more channels out there?

Social media, I know it’s a popular buzzword. But I don’t know if it’s social media—it’s more like connected awareness. People are into “discover.” They’re no longer stuck in a lane where they only see what’s in front of them. Consumers can discover and find their own identity. Social media happens to be the platform now. What’s nice is that it breaks down the barrier that’s been around forever and makes ways for a new brand with a compelling story to reach a consumer. So I love the fact that I am able to reach somebody who might be a huge fan of my brand who might not have otherwise had the opportunity to hear about it.

So what’s a typical day like for you?

Anything but typical. Call with my manufacturing team at 5 o’clock. Try to get a workout in the morning. I have a brand new dog, so I like playing with him. I try to keep my 8 and 9 slots open for coffee. This is my chance to connect with someone from a different world. I think the more I can listen and learn from other businesses, other cultures, the richer my knowledge will be. I fill it five times a week with people from different backgrounds, different passions. Lunch is filled with strategic meetings, photo shoots, occasional interviews.

And a typical night?

If I’m not home working on my brand, I go to events, a lot of GQ events. There are a lot of opportunities here in New York. I always try to find the best person in the room to further my goal. I like to think of it, if you’re a football fan, as getting first downs. A Hail Mary doesn’t usually work. I like to set my first down, 10-yard goals. And once I get that, I have more opportunities for more first downs. Making accomplishable goals, things I can achieve that day, and at the end of the evening, evaluating what I accomplished that day, setting the goals for the next day, and just moving the ball down the field.

Beyond your brand, what are some of your passions?

I like to think of myself as a conduit for creative disruption. I also consult, for pure enjoyment. I would say that I’ve gotten to where I am because I listen, but I’ve had great teachers and mentors. So what I’m not able to give financially, because it’s still very tough right now, I try to give in time. Whenever I have the opportunity—if someone reaches out, they want to grab coffee or drinks, they want some advice or direction—I love taking those kind of meetings.

I also love reading. I try to do a book a month. My philosophy is that it can be tough to set out to read a book a month, the volume of pages—but the average book is 300 pages, so that’s 10 a day. That’s doable. At the end, I take out a Post-it and I write down one thing I learned from that book. So at the end of the year, I’ve got 12 things from 12 different minds, and I get immense satisfaction out of that.

Do you travel much?

My M.O. has been pack a bag, buy a ticket, land, and figure it out from there. When I was in college, I moved to London—I just knew I wanted to have a different cultural experience. I used to take vacations by myself, travel without a phone, just shut off the world that I’m so ingrained with, and open myself up to new cultures and new experiences. I think that there’s something incredible about traveling and experiencing new cultures, because the only way you can get outside the box is to do just that. When you only do safe things that you know, you can’t fathom what else there might be. I try not to visit the same place, I try not to eat at the same restaurants. The more I can push myself to experience something new, the more understanding I have. Seeing different perspectives has helped me form my own. It helps fuel my inspiration, to be more worldly than one-sided in my approach.

As you’ve gotten to know the brand, what are your thoughts on American Made Supply Co.?

With my personal style, I come from a positive place, an inspirational place, an authentic place. And it just clicked with me. It’s authentic—it’s not trying to be anything it’s not. It’s real. I’m from California, where a lot of the team is. It resonated with me. It’s simple, it’s classic, it’s comfortable. I remember trying on my first shirt... and it became my favorite shirt. Having a chance to speak with the folks on the team, I connected with the entrepreneurial spirit, the honesty of the brand, the fit of the product. It fits very much with my personal style.

What does it mean to you to be “American Made”?

It comes down to freedom. We are so fortunate and so lucky as an American people to have the opportunities that we do. It’s unfortunate that we’ve gotten so comfortable with it that we sometimes take it for granted. But having traveled and seen the world, I realize what an honor and privilege it is to be born and raised in America and have the opportunities to set out and carve our own paths. Granted, it’s very tough. It’s far from an easy path, but I have that opportunity to make my own way, to make my own story. It’s wholly my own. It goes back to pioneers days, setting your foot on the ground and discovering something new. What we were founded on still resonates with me today—that freedom to pursue my passions.

Interview by Rod Kurtz

Photos Courtesy of Rob Gregg

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