John Legend is no sartorial rookie. The 12-time Grammy, one-time EGOT winner, told WWD that he’s “always had an interest in fashion,” and that “it’s part of my job in some ways.” It’s true. He’s fresh off a collaborative collection with Sperry, which includes three original designs: a slip-on loafer, a high-top sneaker, and a 10-eye boot. And as a high-profile celeb, his every move — and thus outfit — makes headlines, making what he’s wearing as much a talking point as what it is he’s doing.

As such, here we are: talking about both — but really, really quickly. Legend’s a busy guy, but he set aside a few minutes for us at his recent Sperry unveiling in L.A. We talked about personal style, his first suit (which was custom-made by his Dad), and what it was like to design shoes.

John Legend

On his personal style…

1.

“I think it depends on if I’m going on vacation or going to lunch with friends on the weekend or if I’m on stage. There are different moments for different expressions of my style.”

On timeless menswear…

2.

“I’ve always had a good sense for the classics and for tailoring and all those things, but also finding ways to make it more rockstar. I like finding a balance between classic shapes, classic silhouettes, classic tailoring and something more interesting and exciting.”

On dressing up again…

3.

“During COVID, a lot fewer suits were being worn. [Over the past year] I got more into casual wear, particularly during that time because everything was casual, but it’s nice to get dressed up again.”

On his first suit…

4.

“I’ve been wearing suits since my dad first made one for me when I was kid going to church. Both of my parents are tailors, and suits have always been very natural for me. It always feels good to put one on. You feel like you’re put together very well when you wear one.”

On designing his new Sperry collab…

5.

“I was very involved with [Sperry’s] team, and we just went back and forth and exchanged inspiration. We gave them examples from my closet of things that I love and then we talked about the things we’ve done together before. We wanted to include historical Sperry elements but marry those with my sensibilities.”

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