I am incredibly proud to bring you this week’s Five Fits—actually, it’s Three Fits this time around—with the living legend, Smokey Robinson. He looks incredible, and when we met to shoot this, I caught him on a busy day, though I suspect this is the norm for him. He’s still playing live shows and doing press, keeping active and in-touch with his passion. He’s as smooth and relaxed as you’d expect, even in 90-plus-degree New York City heat.

A few accolades worth mentioning: Robinson has a star on the Hollywood Walk of Fame, has been inducted into the Rock and Roll Hall of Fame—once as an individual and again as a member of the Miracles—as well as the Songwriter’s Hall of Fame, has won a Grammy and was awarded the 2016 Library of Congress Gershwin Prize. I could go on, but you get the idea.

I sat down with Smokey to discuss how he fell in love with music, meeting Berry Gordy, what it was like to be in Detroit during the rise of Motown and the auto industry, his approach to style, and plenty more.

Fit One

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Suit by Woody Wilson, shirt and belt by Si Beau Custom Tailor, and shoes by Andres.

Can you recall if there was a first moment you fell in love with music?

No... No, that's impossible. I've been hearing music, in love with music, since I could hear. I grew up in a house where there was always music. So, no, I can't recall that. I was probably two or three years old.

When did you think you'd make a career of it and pursue it for a living?

Well, probably after I graduated from high school when I met Berry Gordy. He was a producer and a songwriter in Detroit, and he had done hits on some of my favorite people. He started Motown. I hooked up with him about a year or so after that.

What was it like growing up in Detroit and seeing the rise and decline of the city?

Excitement then, man. Detroit was bustling. The auto industry was there, and then we started Motown, which created some other kinds of jobs for people, but it was excitement.

What was the biggest moment of adversity in your career that you had to overcome?

I retired for about three years and that was the biggest one for me because I found out that I couldn't find anything to replace this, which is why I still do it now.

Any advice for readers on how to age gracefully and continue to do what they love? What keeps you active and healthy?

Just take care of yourself. After you get to be about 40 years old, your other job is to take care of yourself diligently and on purpose, and you have to do it whether you feel like it or not. I get up every day and I work out. I do yoga. I've been doing yoga for 45 years, and some days I really don't feel like doing that, but I do anyway because you have to.

How about diet?

Well, diet, yeah. I have a pretty simple diet, in fact. I don't eat meat. I haven't had any red meat since 1972. But now I eat chicken and fish again. For a while, I was a total vegan. I eat pretty plain.

Fit Two

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Trousers by Si Beau Custom Tailor, shoes and glove by FootJoy, and visor by Titleist.

When did you first become interested in clothing and style?

When I was probably about eight or nine years old, because I didn't have any.

Was there somebody that you saw that had style that made you think, "Wow, that's cool”?

No, no, no. I would see people on billboards and magazines and things like that, but where I grew up, I didn't have that.

What role does style play in your music and performances?

I think that it is good to try to be—what can I say, what's a good word for it?—as apparent as possible. I like colors. I like colors especially for when we're on stage. I like to be loud sometimes—pink, yellow, all that. In my personal life, if I'm going to go somewhere daily, I'm in jeans, unless I'm going to go to the golf course. I have golf outfits, but if I'm going to go somewhere dressy, I have suits and clothes that I put on for that particular thing. Basically, my everyday garb is jeans.

Can you remember the first significant purchase you made? Maybe when you got your first big check.

My first significant check thing was not something that I bought to wear. I remember the first time Berry, who was my best friend, was still married to a lady named Raynoma [Mayberry Liles] then, and I was married to Claudette [Rogers], and I got my first check in my life for a $1,000, and I thought that I was a millionaire. I said, "Okay, this is a million dollars right here." Because I never thought I'd ever have $1,000 at one time for myself, so I took everybody out to dinner.

Fit Three

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Suit by Si Beau Custom Tailor, shoes by Andres, watch by Movado, and jewelry, a gift from his wife, Frances Robinson.

Do you have an all-time favorite outfit?

No. I love outfits, so I don't.

I was told you have a hand in all of your stage outfits.

I pick the fabrics from dealers. All the clothing that you see me in, personal or on stage, I design it. I pick out material, and I have two different tailors. I tell them what I want.

How many suits do you think you own?

I have no idea.

Is it a crazy amount?

Yeah.

What does the average day in your life look like these days?

Some days I have nothing but work. I have a channel on Sirius Radio now, so some days we're doing that, or my social media people are calling me to do 10 things a day. But if I don't really have anything planned or anything to do, which is one of my favorite things, I go play golf. And if I can't play that day, I'll just go and hit some balls at the range or something like that.

If you had to wear one outfit for the rest of your life, what would it consist of?

My birthday suit.

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