John Legend on His Sperry Collab Drop

Crossing the threshold into becoming one of the world’s firsts isn’t easy. 12 Grammy awards? Check. Academy Award? Check. Emmy, Golden Globe, and Tony? Check, check and check. Besides being the world’s first Black man to snag an EGOT, John Legend’s resume also includes winemaker (LVE), producer (who knew he was a producer on La La Land? Not us), TV host (The Voice), and philanthropist (Human Level and #FREEAMERICA).

Next up: his design collaboration with Sperry, The Sperry Legendary Collection drops today. The collab was birthed as the result of a natural next step for Legend, who is Sperry’s brand ambassador and has been curating shopping edits for the brand for the past year. This new opportunity allows him to marry his personal taste with Sperry’s heritage into a signature collection.

Sperry itself has a deep brand history rooting back to 1935—the founder Paul Sperry created the world’s first boat shoe. The definitive Sperry boat shoe, now an everyday and dockside classic, originally pioneered anti-slip technology and remains a leader in the category today. The collaboration with Legend feels like a perfect match between two innovators: with Legend bringing new style and edge to Sperry’s well-respected, classic, and functional products. 

The collection features a signature Boat Shoe, Commodore Boot, and Tall Boot. Below, we spoke with Legend about bringing the collection to life and creating something that would fit right in with his own personal style.

LEO: What sparked your interest from being a brand ambassador at Sperry to designing for them?

JOHN LEGEND: We have been working with them and having a lot of fun with the collaboration over the years, but felt the next step would be that we build something new, instead of recommending an edit of styles. [We] embraced the heritage of the brand and incorporated more of my own personal style and taste into it. Working with their design team and my stylist, Dave Thomas, we came to reference the shapes that I like to wear myself and connect that with the traditional Sperry style to create something new. It’s been so much fun. The motivation for me was finding ways we can build something new that I would be excited to wear, show to my fans, and that would make my outfits better. 

“I know I can’t do all of this on my own, and it’s important for me to work with people who know their specialty really well. You can come together to make something really cool together.”

What was your creative process during the design process in comparison to, say, writing music? 

In some ways, they are similar processes because a lot of it is about collaboration. Whether it is music, design, or winemaking—which I also do—a lot of it is about finding the right partners and people you trust, respect, and believe that you can make something great together. It is about continuing to innovate until you get it right. With music, we will keep working on something [or] keep mixing it, turning up the guitar or down, until we get that exact right balance. I found that working in visual design is similar where you are trying to get that balance exactly right. Part of it is about finding the right materials, shape, [and] little pops of color or things to make it unique or interesting. You get it right [when] everything balances correctly, and I think we tried to accomplish that.

How did you infuse your personal style into this collaboration? 

We went into my closet and talked to my stylist [Dave Thomas] about the things that I really love to wear and tried to find a way to connect that with what Sperry already does. That was really the crutch of it—finding the connection between my personal style and Sperry’s heritage; finding ways to bring it together, refresh it, and make it personal. 

Which shoe will you wear the most? What do you think is going to be the most versatile piece from this collab?

I love the texture and shape of the boat shoes. I feel like I’m going to wear them A LOT. I also love the white sneaker which will be a part of the Spring collection which comes out this December. I love it because it goes with so many things, and the right white sneaker can make an outfit so much better.

“I think a huge part is being humble enough to know that you don’t know everything and finding really good collaborators to make you better.”

You have had such a long and impressive creative career. What would you recommend to other creatives who want to branch out into different creative projects?

A lot of it is about finding the right collaborator. I know I can’t do all of this on my own, and it’s important for me to work with people who know their specialty really well. You can come together to make something really cool together. I think a huge part is being humble enough to know that you don’t know everything and finding really good collaborators to make you better. You then go into that collaboration with all your creativity and all your passion but also being open to other people’s ideas. 


Photo Courtesy of Sperry

Sperry x John Legend Signature Boat Shoe

The Sperry x John Legend Signature Boat Shoe takes Sperry’s iconic Authentic Original to the next level. Part loafer, part boat shoe, this sleek deconstructed style comes in butter-soft suede and offers a pared-down aesthetic with no hardware or shoelace eyelets. Instead, laser-cut details suggest the traditional 360 lacing which is a signature element of Sperry’s classic boat shoes. A fixed lace detail on the tongue allows for easy slip on and off.

Sperry x John Legend Commodore Boot

The Sperry x John Legend Commodore Boot plays off of Sperry’s best-selling chukka and raises the height to complement Legend’s weekend wear. This style is made with Sperry’s PLUSHWAVE technology, and the shoe is extremely light and extra comfortable. A clear outsole reveals a holiday-themed red and green tartan, inspired by Legend’s holiday album, and features the word ‘Legendary’ in the pattern.

Sperry x John Legend Tall Boot

The Sperry x John Legend Tall Boot takes inspiration from European runway collections. Building on Sperry’s design DNA, the 10-eye mid-calf high boot features a laser-cut detail that references Sperry’s classic 360 boat shoe lacing. A Vibram outsole features chunky traction lugs and is crafted with a double-layered welt. Unique leather pull tabs embossed with the Sperry Legend logo are placed at the tongue and heel to help pull the boot on and off.

The Sperry x John Legend Collection drops today. Available exclusively at Nordstrom and Sperry. Prices range from $120- $250.