Charlie Wilson Wears Two Watches to Remind Himself He's Made It

Welcome back to Fit Diaries, where GQ asks our favorite style lords to document a week through their outfits. Up next: Charlie Wilson, the R&B luminary who's been setting the mood since the early '70s, worked with everybody from Kanye and Bruno Mars to Tyler, the Creator and Aminé along the way, and just dropped a brand-new single called "One I Got" that's guaranteed to lift your quarantine spirits.

When Charlie Wilson first landed on the scene in 1974 with The Gap Band-the funk trio he fronted alongside his brothers Ronnie and Robert-he wore a lot of cowboy hats. "We were Oklahoma boys," the legendary crooner tells me now, over the phone from his home in LA. "We made those cowboy hats look a lot different than anybody had seen before on our records and album covers." The same way you can still hear echoes of Wilson's soaring melodies from that period all over the charts-right next to his own recent singles like "Forever Valentine," which hit #1 on Billboard's Adult R&B Songs in May-he's been proud to see nods to his Western-inflected style popping up in 2020. "I wore a white Zorro-style hat back then, and I've been seeing a couple of disc jockeys wearing those now. I saw Lil Nas X with his fringes on, and I thought, 'He looks like Charlie Wilson back in the day!' It's cool, man. It looked good on him!"

These days, Wilson-or Uncle Charlie, as everybody calls him, since Snoop Dogg first coined the nickname in the '90s-dresses a little more relaxed. "Casual, flipped out, crazy, with a whole lot of swag," he says, when I ask him to describe his style. Even though he's spent his quarantine mostly shuttling between his house and the studio ("If I have to be out in public, I better have a hazmat suit on, man! Next time you see me, I'll look like I just came from NASA!"), he's still doing his best to have some fun and take a few risks with his wardrobe. But not too many risks. "My wife won't let go out the door with some of the stuff I have in my head," he laughs. "'Oh, no, you just turn right on around and change because you ain't wearing that!' I don't get to flaunt some of the stuff I really want to wear. She makes sure I stay on point." -Yang-Yi Goh

Monday

This is just a chill look to start the week. I was going to the studio, and I knew I was going to be there until after dark, so long sleeves are a must. It's a good shirt for me, because I'm kind of clumsy with food. [ Laughs.] If I spill something, it's all good-I can just rub it in and pretend it was supposed to be there.

I like my socks to be thick and soft. I got some Golf Wang socks from Tyler, the Creator on, and they're so soft that when you walk around, it feels like you're in some plush house shoes. Tyler's the kind of guy that can get away with [wearing] anything, because when he puts it on, he can own it. He can go to the edge, because his music goes to the edge that way. Some of those things I can't always get away with. [ Laughs.]

I've been wearing glasses for a long time-since the '70s, when shades were really cool to wear. I was wearing them even before that, and I just kept them on all of these years. Sometimes my wife or assistant will say, "No, no, don't put those shades on today." And I'll be like, " What? I feel naked!" For me, man, it's just part of my attire. I can really size a person up with them glasses on.

Tuesday

I have a lot of tracksuits, but this Gucci suit is one of my favorites. The first time I wore it I was in South Africa. I visited the Gucci store there and [the staff] started freaking out, like, "Ohhhh, Uncle Charlie's in the building!" I got the Gucci tennis shoes on to go with it. It's just like a Tuesday kick-around suit that I can lounge in and lay down in it, and it doesn't wrinkle up or look funny. And, as you can probably tell, my shoulders are looking good because I've been lifting weights. [ Laughs.] I got some definition in those arms!

I wear two watches-one is to tell time, and the other is to tell me what time it really is. I'm not a braggadocios kind of guy, but I do like to let myself know that I'm capable of having whatever it is that I want to have. I usually keep the second one on Oklahoma time, so I can call family members and know I'm not calling too late.

The key on my necklace is a symbol of my love for my wife. I've got the key to her heart, and she has a heart that she doesn't wear that much. She'll touch the key, and I'll say, "Watch out! I don't see your heart on! I guess somebody else got the heart for this key." [ Laughs.] Then she says, 'Watch yourself, buddy. Watch yourself.' We have fun everyday. She's my best friend. You gotta have fun, or you're going to let it tarnish and die out. You try being with somebody seven days a week, 24 hours a day, for 26 years-not one day apart. That's friendship and love right there.

Wednesday

I have this tracksuit in a few different colors: mint green, black, about three or four of them. What drew me to it was the design-all of the movement in the jacket is amazing. It reminds me of some of the artwork in my home, most of which is Middle Eastern, because my wife is Middle Eastern. Happy wife, happy life, you know? All of the carpets in my home are Persian, and a lot of the art framed on our walls are Persian carpets as well. Really beautiful stuff. So it all just kind of fits.

Thursday

I was on my way to a special little dinner with my team and management. This jacket is a Ryan Seacrest jacket. I like his prints and the style of his jackets, so I have maybe five or six of them in my closet. I like his dress shirts, too, I wear those to awards shows. I know Ryan a little bit-I've been on Live with Kelly and Ryan a few times, and I make them dance with me every time I'm there-but I've never actually worn the jackets around him. That's a little cheesy. [ Laughs.] "Hey Ryan, come here for a second! Look inside the collar, buddy!"

Friday

It's Friday. Sun's out. Going to Habit to pick up some burgers and eat them outside under the umbrellas. It's cool, man. Ami T-shirt, Vans, and my Frame jeans. I like these jeans because they hug my body: my waistline, my legs. And they're kind of stretchy, so they just feel good. The heart on my tee is like a little nod to my single "Forever Valentine" with Bruno Mars, and the flowers on my Vans kind of fit that theme, too. The ring I'm wearing is from my wife-she buys all of my jewelry. She saw this emerald ring in the store and put it on my finger, and before I could take it off and give it back, she'd bought it for me. We work real hard, and when she wants to do something she just does it for me, to show her love and appreciation. She makes sure that I know I can get what I want now.