Why Comedian Roy Wood Jr. Will Never Wear a Football Jersey Onstage

Roy Wood Jr. doesn’t shy away from the un-funny issues facing the nation today: He’s as likely to joke about Americans’ passive attitudes towards individual shootings as he is about shopping. In a segment on The Daily Show last week, for instance, Wood asked author Dan Gardner, “I know the world is ending, so why is it so hard to do anything about it?” Wood was holding a burger at the time, to make a point about apathy in the face of certain beef-catalyzed climate doom.

But to take on the big issues, you first have to tackle the small issues, like your onstage wardrobe, or the ups and downs of parenting. We spoke with Wood about his style rules (no more than two colors at a time) and his dad hacks (separate compartments for liquids).

Bonobos: So what happened with your kid today?

Roy Wood Jr.: He bit a kid that had scratched him earlier in the school year. I had to go back to the school. It’s weird, because your child will do something and your first instinct is to defend them no matter what. Then they tell you what they did and you go, yeah, okay, I can see how that one could be an issue. But he’s two. He’ll be turning three soon. Two year olds, they bite. They gnaw. They scratch. That’s what it is. I’m proud of him: He held this grudge for months and then waited for the right time to strike. Like a Wood.

Now that you’ve been a dad for almost three years, what’s the most dad thing you do now that you didn’t do before?

I wake up at 6:30 every morning. I did morning radio for 12 years, and I hated waking up. Absolutely hated it. Now I’m getting up and making the oatmeal. I also had to buy a bigger laptop bag to fit his snacks. My son likes a lot of liquidity, juicy snacks—he’s a yogurt guy. Pouches of juice and liquid just don’t belong around an Apple MacBook.

In your appearances you’ve joked about hating shopping. Under what circumstances do you voluntarily go shopping in-person?

When I’m looking for clothing for television appearances, I have a stylist. But I still like going out and seeing what’s on the rack. There’s still something about touching the clothes and actually trying them on that the Internet doesn’t give you. The gratification of Internet shopping doesn’t come in the delivery. When the item arrives, you say oh yeah, that thing I bought four days ago. Then you put it on twice. You realize you don’t look good in it. Then it sits at your door for three weeks while you pretend to get ready to mail it back.

Do you think you actually buy different stuff when you shop in-person?

I call myself a “snaker” where I go to the grocery store. I snake up and down every aisle. Then I leave because you never know what you’ll need until you see it. The Internet doesn’t lend itself to browsing in that regard. You won’t see and discover a lot of new stuff. The Internet algorithms show you more of what you’ve already purchased. What if I want something completely out of left field today?

You mentioned shopping for television appearances. How did you dress at the beginning of your career when you were doing stand-up and how has that changed?

When I first started, I was 19. I was 6’2 and 170 pounds. Just for scale, I’m 240 now. I was 19 but I looked 14. No one took my materials seriously. No one would pay attention to me, so I wore suits — basic off-the-rack stuff. The suits added a little bit of age. Then I went through a phase when I was doing a lot of colleges. There were a lot of t-shirts and half-zips — maybe a blazer. In my 30s I completely let go of the blazers and started doing bomber jackets and things like that.

And now?

I’m 40 now, and somewhere in there my material turned. It became something a little more opinionated. It had a little more teeth. I had opinions. I had stuff that I need you to listen to. I lost the prints. I just wore a bomber and a nice shirt, or a nice shirt with the sleeves rolled up. I’m not a flashy guy on stage. I’m not Jamie Foxx. I’m not Kevin Hart. Chris Rock’s wardrobe is as bold as the jokes he tells. But then you look at someone like say Jim Gaffigan. You’re not getting a lot of flash at a Jim Gaffigan. It’s a wardrobe that reflects the persona, which is very much, “Hey, I’m just a regular guy. These are my kids. This is my wife.” It’s not larger-than-life tales. It’s something more relatable. I like for my clothes to be as classic and as simple as possible.

When does a look become too bold?

For me, the general rule is two colors: No more than two colors at a time. Pretty much every late-night appearance, it’s a jacket and button down—that’s pretty much been my protocol, all the way back to Conan and Letterman. But I never want to do more than two colors on my person. I had a little bit of multicolored floral, but it was very subtle. I don’t wear jewelry. I’m not a jewelry guy. You might catch me in a watch once a month.

What compels you to wear a watch on that one day?

The watch days vary depending on what mood I’m in, and what the outfit is. Even if I wear a watch, I promise you it’s not set.

What clothes or accessories doom a set?

My girlfriend bought me one of those Kanye-West-looking-ass pullovers. It’s nice. I like it. I wear it. But never on stage: I wore it on stage one time and the set wasn’t good. To this day I blame the wardrobe. I also don’t wear sports jerseys on stage. There’s something about sports jerseys that for me immediately says: Dude. Bro. I went onstage in a football jersey and I bombed miserably. And shorts. You can’t be up there in a football jersey and shorts talking about racial equality and police reform. You need a collar. You need a nice jacket.

What’s the point in your career when you can wear shorts and a jersey on stage and say whatever you want?

I saw Damon Wayans on stage one time in a very high-end trench coat. He had one of those leather backpack man bags or whatever. When you go back and look at his comedy from the 90s, you would never imagine that that guy became the guy on stage. Of course, the material is more bold, so it fits. I don’t know when you get that status. I do think that as a black comedian, speaking to black audiences, your clothes speak before you open your mouth. When you walk out, you need to tell the audience, I respect you. I respect the money you spent and the time you decided to commit to this event. By showing up in a t-shirt, you’re making it harder for yourself. Dave Chappelle can just be an regular t-shirt. Sometimes he comes up in a full army jacket. Sometimes he’s in a muscle shirt—just a sleeveless muscle shirt. It works for him because everyone knows who he is. People are still learning me.

Lauren Larson is a writer and editor in New York City, aspiring to be a writer and editor in Bali.

Photos by Meredith Jenks.