Exclusive: John Legend Talks Collaborating With Sperry, Work and Family & Raising His Voice for Social Justice

John Legend is the ultimate work from home dad. When the star opens the doors to his family’s new home in Beverly Hills, Calif. — not far from their previous digs in the celebrity enclave — it’s clear that the Legend household accommodates everyone and nearly everything.

As the musician, who just moved in a few weeks ago, gets ready for his FN cover shoot showcasing his collaboration with Sperry, son Miles, 3, is having breakfast in the kitchen with Legend’s brother Ron, who is also his hairstylist. Meanwhile Pepper, wife Chrissy Teigen’s mother, is chatting with the house manager, while Legend’s stylist, Dave Thomas, prepares looks not just for the shoot but also for Legend’s appearances on “The Voice.” Assistants and movers are also onsite, as a handful of children arrive at the front door who are part of a school pod that the 42-year-old and Teigen have been hosting at their home.

john legend, sperry, burberry suit, gucci shirt, sperry shoes
John Legend wears a Burberry suit, Gucci shirt and Sperry shoes.
CREDIT: Yu Tsai

Soon, the Grammy winner emerges from down the hall and makes his way toward the lawn — looking typically dapper in a pale-blue Burberry suit and a Gucci shirt with a red collar and cuffs that match the tassels on his Sperry loafers. While Legend poses for the camera, Miles is also outside, where he and his friends bounce on a trampoline and enjoy a farmer’s market playhouse directly behind the superstar, just outside the frame.

Before moving inside for filming, Legend walks hand-in-hand with Miles and asks what he’s learning in school that day.

For Legend, this work-from-home sequence amid the pandemic has given him more time for family and creativity as concert touring has been halted. It’s also yielded an abundance of inspiration for his Sperry partnership. “I don’t usually write when I’m on tour, so not being on tour means I’ve been more creative,” Legend said of how he has adapted. “It means I’ve been writing more songs. It means I’ve been able to engage with creative ideas more. It gave me more time to focus on this [Sperry collaboration]. I think I’ve been more creative during this time than I normally would be because I’m not running around as much.”

Despite the constraints of COVID-19, his shoe collection was created over Zoom, and Sperry’s product team also conducted a tour of Legend’s previous home to identify inspiration sources from elements of his lifestyle.

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John Legend x Sperry Tall Boot.
CREDIT: Courtesy of Sperry

Since joining Sperry as an ambassador last year, Legend has launched three curated edits of the brand’s shoes. Now, he’s preparing for the release of his debut collaboration featuring three distinctive styles due in fall, including the Sperry x John Legend Boat Shoe — Sperry’s first cupsole boat shoe — which is intended to be Legend’s everyday relaxed style. There’s also a 7-eye lace-up Sperry x John Legend Commodore boot designed for his casual weekend wear and a Sperry x John Legend Tall Boot — a 10-eye lace-up with a medial side zipper on a Vibram outsole that can be worn with his designer suits. “We made [the Tall Boot] with some height that they weren’t used to over at Sperry, but they were into it,” Legend said of the new silhouette, which looks like an elevated combat boot with inspiration from Sperry’s boat shoe heritage.

“I’m glad they were willing to do something a little different with us. We tried to tie it to some shapes and soles and styles that they already had, but make it new and fresh, and clearly reflective that it was a collaboration,” Legend explained.

The artist sees the collection as versatile enough for leisure activities and special occasions. And it’s no surprise that Teigen, who is often seen by his side, had an influence. “I’m always trying to look good for her, and that’s part of my inspiration — just wanting to look good next to her because she’s always going to look good,” Legend said. “I feel like with all these styles, I feel confident standing in them next to my beautiful wife.”

The lineup comes with details unique to the entertainer, like keyboard prints on the insole, “JL” logos, as well as quotes on the inside of the tongue that wax poetic on love, soul and authenticity. Ultimately, Legend wanted something that wasn’t “too busy and fussy,” he said. “Everything that we worked on, we were like, ‘do we need that extra thing?’ Let’s take that away, take this away too and just keep it as lean and clean and elegant as we can.” The drop date is Sept. 15, and prices will range from $120 to $250 at select retailers and on Sperry.com.

Along with sharpening the finer points of the design, Legend discovered the unexpected constraints and technicality behind footwear production. “When you get into the details, it’s like, oh, well, if we do that, it’s going to take this many months to come from this factory. You never think about that when you’re just wearing shoes,” he explained. “And just because you have an idea, it doesn’t mean it’s readily doable. There’s a lot of ingenuity that goes into making those things happen. It’s not that I didn’t think that was the case, but once you get into it, you truly respect the craft of bringing this aesthetic idea to life and a shoe that’s available for the mass market.”

Keeping the looks refined with some vibrancy — a reflection of his own style — was an imperative for Legend, whose fashion savvy began early as the son of two tailors who made his church suits when he was a child. In high school, Legend and his brothers embraced a “preppy aesthetic” and developed an early connection with the Sperry brand. “We were into Hilfiger and then Nautica, and the preppy shoes like Sperry and Eastland and things like that,” said Legend, who recalled the style influence on his upbringing in a “blue collar” Ohio town. “It wasn’t because we came from that culture, but it felt kind of aspirational to us.”

An Ivy League education at the University of Pennsylvania and an early career in the business world also influenced his current fashion sense — an amalgamation of those cultures with the flash of an entertainer. “I think my style has always been a blend of classics — classic shapes, styles — and then things that add color, add energy, so that it doesn’t feel like it’s just your everyday thing,” Legend said. “I’m going on stage and on ‘The Voice.’ I’m in circumstances where it’s not enough to just wear something classic that’s well-fit.”

Legend has help crafting his looks from his stylist, Dave Thomas, who translated the musician’s taste into the capsule alongside Sperry’s product creation team. The result? A more fashion-forward course for the brand. “Something that we look for with all collaboration partners is someone who can stretch us in new directions while still retaining our Sperry DNA,” said Elizabeth Drori, chief marketing officer. “John Legend and Dave Thomas were able to do that for us, so we’re really pleased with how the product turned out.”

And the brand expects to generate significant heat around this harmonious remaking of Sperry. “The product itself is so great, and the combination of John representing [it] has been quite a selling point. And then in the back half of the year, we have public appearances planned with John,” Drori added. “There’s opportunity to create excitement around the launch and connection points with consumers and with our retail partners. There’s a lot that we can bring to the table.”

Earlier this year, Legend pivoted from his releases of curated selections of Sperry’s line toward serving as the face of the brand’s product stories, including its Gold Cup and Soletide lines, which have been successful in driving new customer acquisition, Drori said. “We can see it in our ad performance and homepage performance. We see it in increased click- through rates and engagement rates.”

Leveraging Legend’s global appeal is part of a strategy to court new consumers, particularly a younger demographic, to a label that’s been around for more than 80 years — and has been worn by their grandparents. “We wanted to achieve broadening our reach so everybody knows the brand,” said Brendan Hoffman, president of Sperry parent Wolverine World Wide Inc. “[Sperry’s] been around for all our lives, and yet it still has potential to reach a newer customer, a younger customer, a tightly knit customer, so finding somebody like John, who was so authentic to what we were trying to do, was critically important.”

Sperry, with its 327,000 followers on Instagram, has tapped into Legend’s nearly 14 million-strong fanbase to generate awareness of the brand and expand consumer engagement to the iPhone generation. On the social media platform, his content serves as an authentic journal of his life — an intimate look at his time with Teigen, Miles and daughter Luna, as well as a behind-the-scenes glimpse into his role as a judge on “The Voice” (where he wore Sperry to the season finale). He also shares his social justice activism and brand partnerships.

“He’s been on our social channels, but we’ve also been on his, and they both added value,” Drori said.

Alison Bringé, CMO of Launchmetrics, a software and data insights company with a focus on fashion, beauty and luxury, said that the social media exposure is “impactful” for Sperry, where a single post on Legend’s Instagram account can average 55 times more Media Impact Value than one from the brand itself. (MIV is Launchmetrics’ algorithm that measures the impact of relevant media placements across all channels — online, social, print — inclusive of paid, owned and earned media.)

Drori explained, “People love John for his personality and warmth, so this year we produced a lot of content that is sort of like TikTok videos.” Think cleverly edited clips that show Legend quickly putting on Sperry shoes. “We’ve had those videos on our homepage and our repeat advertising on social, and they performed really well. Together with our content across channels, it has driven consumer engagement and a lot of interest,” she said.

And there’s more to come in spring ’22 as the collaborators plan to release a follow-up collection with similar styles, as well as one new product. For Legend, expectations will be high. “When I think about goals for myself, I think about creative goals, like I want this next album to be better than all the ones I’ve done before. I want this next collaboration to be better than all the ones I’ve done before,” he said. “I’m always thinking about the goal of being a better creator, being a better artist, being the best version of myself that I can be as someone who puts new things out into the world. That’s usually what my goal is.”

Aside from working on the forthcoming release, as pandemic restrictions wane, Legend said he’s eager to return to the stage and make in-person connections again after hosting virtual performances throughout the year (including a Sperry Zoom holiday party) and engaging with a virtual audience on “The Voice.”

“I want to go on tour. I want to be in crowds and enjoy just human contact and an interaction,” he said. “I’ve missed it.”

Legend also has other passion projects, particularly his social justice initiatives. Last January, he performed Nina Simone’s “Feeling Good” at the footsteps of the Lincoln Memorial in Washington, D.C., for an Inauguration Day TV special honoring President Joe Biden and Vice President Kamala Harris. Since then, a divisive political climate — fueled by former President Trump’s false claim that he won the election — has resulted in the passage of voting restrictions in several states across the country. So Legend is using his powerful voice to raise awareness about the situation.

“An urgent issue is making sure we actually have a democracy that is accessible to everyone who’s eligible to vote,” Legend said. “There are a lot of forces out there lying about what happened in the last election and using that as a pretext to take people’s voting rights away and or make it much harder for them to vote with the intent of suppressing their vote. I feel like the most urgent concern for Americans should be, are we going to have a real democracy where we try to make it as accessible as possible for everyone to vote and actually respect the results of those elections?”

Legend has also been an advocate for ending mass incarceration through FreeAmerica, an organization he founded with his partners in 2014 that’s dedicated to the cause. “I’ve gotten involved with a lot of those issues around reforming the criminal justice system,” he added. “That’s something I continue to work on. But I think, honestly, the most urgent priority is are we going to have a democracy or not? And hopefully, all of us who care about the people’s voices being heard in our government, we’ll fight for that.”

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