John Legend Sounds Off on Buying Heels for Chrissy Teigen, the Riskiest Shoes He’s Ever Worn & More

John Legend stars in this week’s FN cover story. The musician invited us into his new home for a chat on his fall Sperry collaboration, work and family, and his social justice initiatives. Legend also talked about cleaning out his closet, the shoes he buys for wife Chrissy Teigen and the riskiest pair he owns.

Your Favorite Pair of Shoes as a Kid

When I was a kid, my favorite pair of shoes were my cowboy boots. I would wear cowboy boots with cowboy outfits. I would wear them with non-cowboy outfits like shorts and a tank top in the summer. It didn’t matter. I loved my cowboy boots.”

The Shoes You Wore in High School

I was pretty into a lot of preppy clothes in high school, which, basically i’m into now, too. So I wore Sperrys or Eastlands. Loafers that looked cool with khakis. I didn’t come from a preppy lifestyle.”

What Shoes You Wear With Your Kids

With my kids, it depends on our activities. When we’re going out and doing playful activities, I want to wear shoes that I can run around in. I usually like to wear a low-top sneaker with some shorts when I’m out playing with the kids.”

What Shoes Your Wear on Date Night

“On date night, it’s a range, so I usually like to do kind of dressed up, but not too dressed up when we go out on a date. I’ll usually wear a jacket, maybe something like this. Actually, this outfit is a little daytime for what I would wear for a date, but I would wear some loafers and a suit and an open collared shirt.

How Many Pairs of Shoes You Own Right Now

“We just moved into a new place and I tried to cleanse my closet enough, so I got rid of a bunch of shoes. But I still have probably about 70 pairs. Is that a lot of shoes? I feel like it’s a lot of shoes. Should I be embarrassed? My brother has more. He has a sneaker collection that is out of this world.”

What Pair of Shoes Have You Had the Longest?

“I feel like probably some patent leather dress shoes that I would wear on a formal night because you don’t wear them that often, they don’t get worn out and they’re a classic shape. So, they look good five years later, 10 years later.”

What Shoes Do You Travel In?

“A lot of times I’ll travel in a sneaker just for comfort and ease of moving around and taking off on the plane. And then it depends on where I’m going. You know, am I going to a sunny place? Am I going to New York?”

What Shoes Do You Give as a Gift?

I haven’t given shoes as a gift very often except for my wife, because I feel like I know her taste extremely well and I feel comfortable getting shoes for her, so I’ll get her a nice pair of heels.”

Favorite Pair of Shoes in Your Closet

I love boots right now. I’m really into boots and so I have a few pairs of  black boots, brown boots — just a good boot that looks good with a jean I’m really into right now.”

Have You Ever Worn a Shoe With a Heel?

I’ve definitely worn shoes with a heel — boots, usually, like the shape of a Chelsea boot, but a little elevated in its height. I’m not especially tall, so I don’t mind the extra couple of inches.”

The Craziest or Riskiest Shoes You’ve Ever Worn

I have these really interesting Balenciaga boots right now, like the heel goes inward, it’s very triangular. It’s a little forward for me. Every once in a while, you got a rock star it up a little bit.”

The Pair You’re Most Guilty of Owning

I do not feel guilty about any of my clothes. I feel like I bought them because I like them and I want to wear them — no guilt. People always ask me about guilty pleasures in music, too. I’m like, I do not feel guilty about any of it. None of it.”

What Pair Will You Never Get Rid Of

“The ones I don’t want to get rid of are the classic shapes that I feel like will always be in style, will always be useful for an outfit. So, cool loafers. Sperry makes great classic dress shoes and a classic white sneaker. I think all of those I will keep for a long time if I like the shape, but I like how it feels and it holds up pretty well. I’ll probably keep those styles for a long time.

The Shoes I Designed

“I love a good boot and some of my boots go pretty high up the leg. With the new collaboration with Sperry, I think you’re going to see how we incorporated that into the brand.”

The Shoes You Wear at Home

“I rarely wear shoes around the house, but I do love how comfortable Sperrys are. They feel like you’re wearing nothing. The loafers I have on right now, they feel like I’m wearing nothing. So, it’s like I’m barefoot at home, just comfortable and stylish.”

BEST GROUP Photo by Angelo Lanza Sponsored By ITA

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