Duke & Winston set for revival as owner Seun Olubodun learns (and prospers) from mistakes

Walking into the Chestnut St. storefront of Duke & Winston was an experience all its own. A bright, open space conveyed cheery U.K.-inspired fashion of all types. 

In the front of the house was Duke, owner Seun Olubodun’s prized English bulldog sleeping in a chair. A source of inspiration for the brand, Duke over time became D&W’s unmistakable face. And in its heyday, Duke was customarily the first face people saw.

What they didn’t see while Duke unknowingly posed for Instapics in the front was Olubodun, living out of the back of the store, feeling chained to a vision he no longer wanted any parts of. The story of Duke & Winston was a cautionary tale for any young up and coming entrepreneur to see what can happen if there wasn’t a strong team in place. Duke and Olubodun were it, and despite Olubodun’s desire to see his brand become a success, the weight of it all simply proved too tall to bear.

Fast forward to now, two years since Olubodun closed the doors on his brick and mortar shop and you’ll find a renewed spirit. Fortified by a Texas-based venture capital firm and a team chocked with the business acumen, Olubodun has plans to relaunch his brand later this spring as an online-only retail and wholesale shop.

Before all of that, Olubodun sat down with Philadelphia Weekly to retell a tale of loss, redemption and hopefully success in his own words.

What can Duke & Winston faithful expect from this revival? What’s different about you and the apparel you’re creating?

Well, I think what’s vastly different is that this time I’m not a one-man show. I’ve always strived to be a much bigger brand, but that’s really hard to do when you think you can do it alone. Obviously, I had the staff and all of that [in the first iteration], but even still it was definitely too much. I just had no time to kind of step away and develop a real strategy for growth. Before, it was just about maintaining huge retail space which was pulling me in so many different directions. So this time around our goal is to keep grip. We’re going just e-commerce, completely online, along with a wholesale division. That last part is important because I was having a lot of success with collaborations and partnerships with other brands or national organizations that fit with the [Duke & Winston] brand. So I’m really focused on this go-around to do a lot more of that stuff.

When do you plan to unveil the new line and new looks?

We’re looking to do a soft unveil in the second quarter of this year, just to introduce some new product, but we’re going to be really slow and strategic with our growth. I mean, I want to become a national brand and it’s going to take a couple years to get there. So over the next couple of years, I’m going to be doing this slowly and really calculating everything we put out to the world.

When did it become clear for you that the first iteration of Duke & Winston just was not going to be sustainable long term?

The beginning of the end was like two years in the making. You know, I guess I thought that I would build this great thing and that all this help would just arrive constantly from an operational standpoint and that we’d secure investors because we’d become a pretty established brand in the city. But you know I didn’t. I was working like 20 hours a day in the back of the store [and] as the face with only a crew of younger employees from college. I was completely overwhelmed. I began literally living at the store in the back because it just made sense than to go back and forth.

What was watching that like?

It was difficult. I mean I had an online business that was doing well but the store was failing. There were customer service and inventory management issues, and we even had a flash mob in the city that affected the store. Plus, on top of all that I was going up and down the East Coast doing trunk shows, so I wasn’t in front of customers anymore I was just like dealing with this mountain of stuff. When I knew I had to shut it down, I just retreated to within myself. Man, let me tell you, to be alone with thoughts of failure, it’s the loneliest, [most dark] place you could be.

Did you suffer from depression? How bad did it all get?

So, yeah, let’s get into it.  We closed the store in Dec. 2015, and I was laid up completely out of it until the middle of 2016. I had to pack up everything and move it from the store and put in in my tiny apartment in Northern Liberties. I tried for a short time to keep the business online going but I didn’t even have the energy for that, which was stupid because event then the business was probably still clearly somewhere between $20,000 or so a month in revenue. Everything just went to shit. I honestly packed everything up and I moved to my parents’ house in Providence Rhode Island and I just didn’t get out of bed for weeks. Around the end of 2016, I ran into a friend who lived in California and convinced me that I had to go. He said and I remember that taking the trip out West to step away from it all might just help me to get back.

Despite all the setback, did you consider yourself profitable?

You know, probably not as much as people might think. From the outside looking in when you walked into that store, Duke & Winston looked like a success. But again, it was a one-person shop. I think my best month was Dec. 2014, we generated close to $100,000 in a month. But on average I was only clearly between $40,000-$50,000 a month between the online and retail store and that was all gross profit.

And in the midst of closing the store, going into a dark place, you lose your beloved bulldog, Duke.

Yeah, it was tough to lose Duke, though I will say he lived longer than most bulldogs. Bulldogs generally live between 8-9 years tops, Duke was 12. I really broke down because he was the face of my brand and my best friend for all those years. So when I disappeared, it’s like he basically just kind of like disappeared. I was hoping that he would still be with us to see this second launch and watch us try to make it into a success, but you know, it’s just the way things go sometimes.

Describe Duke & Winston 2.0…

One of the things that was really successful in our first go-around was that this became a brand for dog lovers. We’d have people come in and by a sweatshirt and then buy a collar for their dog. It’s a preppy brand but it’s one that really also resonated with that demographic. So in this relaunch, we’ve put a long of strategy into attracting that core demo, but still creating stuff that people will want to wear. Like people who love brands like Life is Good and Vineyard Vines, but also really love their dogs. So I think this next time around I’m really going to lean in on the customer and his or her dog you know that lives in a city and is really into their dog and dog culture.

You’ve been very active on social media in the announcement of the relaunch. What’s the response been from people that were fans of Duke & Winston?

It’s great because it feels genuine, you know? I’ve gotten a ton of people, like entire families, wearing product. I get letters of support all the time. I always thought of this as a small, niche brand but I never realized the impact it had on a large number of people. It’s been in great in keeping me focused on making sure this relaunch caters to them and people like them in the market.

When you have everything in a row and ready for the masses, what is that relaunch going to feel like?

I knew what it took to get to where we are now, so I’m already content and just seeing this through. Really, it’s more for customers. I want people to know that this was a brand I built from the ground up and that I had no concept of what I was doing for the first 5-6 years. I think failure and rebirth have made this a truly authentic and very homegrown personal brand. There’s a story behind it, one that’s important to share and one I truly hope resonates with customers now and future customers for years to come.


  • Kerith Gabriel's Headshot

    Kerith Gabriel is the former editor-in-chief at Philadelphia Weekly but somehow hasn’t figured out that means he doesn’t have to write nearly as much. As a routine contributor, journalism has been in his blood since his beginnings as a sports writer over a decade ago for the Philadelphia Daily News.

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