James Harris and Lawrence Schlossman, the hilarious duo behind the popular lifestyle podcast Failing Upwards, discuss everything from how they got their start in menswear to their latest obsessions.
James Harris and Lawrence Schlossman met at a sales and PR firm when Harris was an unpaid intern and Schlossman was making, as he says, very little money. But they didn’t seem to care; because as two guys coming up in the fashion industry, they had the opportunity to attend all the coolest menswear events, eat and drink for free, and use any money they did have to buy clothes.
“We were making no money, but we were just happy to be in the room. That’s where we fell in the love with the industry,” remembers Schlossman. “But it was like you do everything you can to make it look like you got it, but in reality… you’re struggling.” Harris adds, “But it was great because we got to see the PR and sales sides of the business. And the highlight was going to Vegas and getting a taste of the glam life. We’d talk to designers and reps and preview next season’s collections.”
When asked if they still have that same love for the industry, they respond in unison, “No way!” Harris laughs, “We’re definitely not as doe-eyed about the industry, but yeah, we still love it.”
After different jobs in the industry, the two reconnected while Harris was at Complex Style and Schlossman was at Four Pins. Harris reflects, “We were there at a time that coincided with the rise of streetwear and the explosion of the sneaker industry. When we were working at Complex, drop culture was about to pop and we were surrounded by the OGs of that world.”
They also admit that being early adopters of social media helped position the success of their podcast. “People have been following us as we failed up to bigger roles and seen us as our personal style evolved,” says Schlossman.
And their podcast, Failing Upwards, has also evolved. It’s not only about menswear, but music, media and memes, too. “It’s a lifestyle universe,” says Schlossman. “We love this industry, but our perception has changed as we’ve established ourselves as guys who can poke fun or take an unpopular stance on issues because we’ve earned our stripes.”
“People have been following us as we failed up to bigger roles and seen us as our personal style evolved.” – Lawrence Schlossman
When asked which retailers are getting it right, they rattle off a long list of stores like Union, Mr. Porter, Mohawk General Store, Nepenthes, Kinfolk, RTH, Undefeated, C’H’C’M', Patagonia, REI, Maxfield, Stussy, and Supreme. “We love Supreme because they do what they’ve always done and never waver,” says Schlossman. “I’m not gonna wear a Supreme box logo, but I wear Supreme jeans every day.”
They also love Dave's New York and they’re seeing a trend of going back to the classics: “Brands like Bass and Clarks. Things ebb and flow, but these brands come back around because they’ll always be good. But the question is, how do you wear it in 2019?”
So, what are they wearing in 2019? On their podcast, they ask their guests what’s the last thing they bought and the next thing they want to buy. “The last thing, and I didn’t buy, I got it for free,” admits Schlossman, “was the Justin Saunders Reeboks. And that was an interesting move by a brand and a good example of how collabs can and should be done.” And what’s next for Schlossman? “I’m gravitating towards tailored and suiting. It’s this idea of casual and easy suiting. I’m trying to be a grown man, but I don’t want to lose that edge.”
Harris says that the last thing he bought was $120 worth of Japanese socks. “I just needed basics that I know will last for years…as long as I don’t lose them in the laundry.” And what’s next? “I’m going back to Sweden, so I’m sure I’ll buy something from Our Legacy.”
So why should you attend their seminar on Tuesday? Harris says, “We understand the circuit and can offer some fun, loud and messy conversation.” Schlossman adds, “We’re charismatic, handsome, smart…we’re the total package. And we’ll have the most entertaining panel at PROJECT…” He laughs, “But we do tend to over-promise and under-deliver.”