Check out the excerpt below.
I’d been a hat guy since I was about eighteen years old. I think I was influenced by stylish men in old black-and-white films and images of jazz cats, when men wearing hats was a standard thing. I never did Yo! MTV Raps without a hat. That was a significant part of my look.
A couple years into hosting MTV Raps, around 1990 or 1991, I took my first trip to Jamaica to cover the Reggae Sunsplash music festival. During some downtime, I went to a craft market in Montego Bay and bought a hat with a particular straw weave. I’ve got a large head and it fit me well. It became a summer favorite of mine. I often rocked it with linen shorts sets Dapper Dan made for me. I rocked it well and knew I looked good.
I was seeing a girl back then and we eventually broke up. The problem was I’d left my straw hat from that Montego Bay craft fair at her house. She gave me some kind of arcane story of where it was or how she’d lost it and soon after our communication broke down. I was like, “Whatever. I need to get a new straw hat.”
To track down another, I had shown a picture of myself in the hat to this African American gentleman at a hat store on Fifth Avenue called JJ Hat Center. He told me that the hat’s weave used to be more common back in the day when hats weren’t mass-produced in China as many are now. Knowing that gave my former straw hat even more cachet. I wanted another, but I knew I wasn’t going back to Jamaica anytime soon. I had friends going to Montego Bay and I asked them to stop at the same craft market to pick one up for me. Since they’d seen me wearing the hat on the show, they knew what I was talking about. Bottom line, the hat they brought back for me was not it. It was just wrong. Months later, I had another friend going to Mo Bay and I asked him to pick one up for me. Would you believe he came back with the same straw hat as my other friends?
The thing that made replacing that hat so imperative was that I was on TV every week. I knew this little show was being watched in millions of homes across America and around the world. It was surreal, because at that time in New York, not everywhere was wired for cable. And still, I was becoming a household name, but only in homes with
cable. None of my friends had cable. I didn’t have cable, so during the first couple of years, I couldn’t watch the show when it aired. They’d messenger me a couple of VHS copies every week and they’d send one to my family in Bed-Stuy because they didn’t have cable either. I’d do the show but still be in my largely cable-free Lower East Side downtown zone, still making art. I took pride in connecting the dots between being a downtown New York bohemian artist and a part of the growing hip-hop culture. Regardless, being on TV that frequently meant I needed to change my on-camera wardrobe weekly. I had to keep my look right, and my hat was an important part of that, kinda like a crown.
American black folks in particular look at what you wear in a certain kind of way, so it was important for me to be stylish but have my own individual Fab style. I came up as a shorty in Bed-Stuy during the time when you could be 100 percent street, but still clean up and put on silk or gabardine slacks, nice casual dress shoes like Playboys, Clarks, or British Walkers, Italian knits, suedes and leathers, and nice hats. I didn’t have real money so a youngin’ like me would put the pricier items on layaway for months, but I always knew what the big kids and fly cats were wearing.
A couple years ago, I heard through social media from the woman I’d been dating back then. She’s got a family now and lives in New Jersey. Everything’s all good—we got on the phone to catch up. In the course of the conversation, she was like, “I’ve got something for you. I think you’re going to be surprised.” A few weeks later, a box arrived in the mail. I opened it and just sat there, like, wow. It was the straw hat. Finally, I got it back.