The British R&B icon fills us in on his wildest and flyest looks.

Craig David Reviews His Best and Worst Style Moments

Craig David is having fun again. In 2000, at the age of 19, the English R&B singer became a global phenomenon with his debut record Born to Do It, which sold more than seven million copies thanks to hits like “Fill Me In” and “7 Days.” David was on top of the world. Not long after that, though, the pressure started to get to him.

“I bought into the hype,” he says. “My second album only sold 3.5 million copies when it was projected to do 10, and I somehow believed them when they told me that was a failure. Can you imagine someone telling you that you sold 3.5 million of anything? You’d be dancing in the streets! When you define yourself by a number, a statistic, a chart position, it’s at your own demise.”

It took him awhile to get there, but eventually, David stopped forcing the issue and chasing hits. “You find yourself in your lows. I realized I needed to go back to being playful, being vulnerable. The last couple records, it’s just been fun.” That looseness has paid off: 2016’s Following My Intuition was his first number-one record since Born to Do It, and this January’s The Time Is Now builds on that success with another collection of soulful, atmospheric bangers.

The other place David’s having fun these days? His wardrobe. At 36, he’s found a sartorial sweet spot of sharp, streetwear-inflected staples that’s equal parts comfortable and sophisticated. But to get there, he first had to go through some—er—growing pains. We asked him to break down some of his most regrettable outfit choices over the span of his career—and a few of his greatest hits, too.

December 2001

“Jeeeeez. You know what? I held it down pretty well. The one thing I was really into at that time—and I haven’t rocked for many a year—was that ‘C.D.’ chain, man. I felt like I had just enough accessories—I had the chain, but I wasn’t too crazy blinged out.”

June 2002

“Like a year and a half ago, I saw in a style magazine that the new trend for that summer was stonewashed denim. It’s come full circle! We’re literally back there again.”

November 2005

“The top half is cool, and you can’t go wrong with those Adidas shell-toes—they’re iconic. It’s just the jeans: they’re a little too on the baggy side. Are you hip-hop here, or are you trying to be classic? I was mixed between the two.”

October 2010

“That’s when you’ve been in Miami too long. You’ve got to calm yourself. Seriously, that’s when you’ve got to get back to the U.K. and make some music.”

February 2013

“Starting to lean back into that classic kind of style. This was just at the point when I started to realize, ‘You know what? You can go even easier than this.’”

February 2016

“Just classic, man. You can’t go wrong with a blue suit and a black top.”

November 2017

“My style now? It’s young and fresh, but it doesn’t feel like I’m trying. It can be high street, but with a pair of the latest sneakers that really set it off. Right now, I’m really into Adidas NMDs. That’s the balance, man—you never want to try to be something that you’re not.”