GQ's Outgoing Creative Director on Michael Jordan, Pleated Pants and Lessons from a 38-Year Career

It’s quite a change for the omnipresent Mr. Moore, 61. Few in the fashion industry have sat at more fashion shows, met with more designers or been photographed with more celebrities than he has. As GQ has shaped and reshaped men’s style over the years, Mr. Moore has been a pivotal part of the process, surfacing new designers and distilling trends—from banana-yellow track pants to full tartan suits—to the masses. GQ launched 87 years ago, which means Mr. Moore has served the title for nearly half of its run. He’s seen the popularity of the suit rise and fall and rise again. In these work-from-home times, he’s made room in the magazine’s pages for slouchy hoodies and track pants. He’s watched a succession of “next big designers” get swept out with last month’s issues.

And so, as he transitions into his second act, I called Mr. Moore to pick his brain for tales and insights from a nearly-four-decade career in men’s fashion.

He first took me back to 1983, when GQ’s legendary editor Art Cooper did away with the magazine’s tradition of putting models on the cover; Mr. Cooper thought celebs were more relatable. That decision changed the fashion-magazine world; increasingly, smiling celebrities became de facto experts on fitness, fashion and relationships. At GQ, the first “named” cover star was Washington Redskins quarterback Joe Theismann, leading off a string of athletes that GQ would mint as style icons. Mr. Moore described styling Michael Jordan in a Glen plaid suit for the March 1989 cover (Richard Avedon took the photograph and, according to Mr. Moore, had no idea who the six-time MVP was). Though Mr. Jordan’s “23” jersey would always be more iconic, “pretty soon everyone was wearing the M.J. suit. For me the floodgates really opened at that point.”

In Mr. Moore’s opinion, athletes are still the ones moving the goalposts style-wise. “In addition to looking at the scores of the games, men are also looking at how an athlete is dressed,” he said, pointing to NBA star Russell Westbrook and the New York Giants’s streetwear-obsessed wide receiver Odell Beckham Jr. as trend-setting stars. If a man is suddenly seeing more athletes wearing top coats today and not as many of them wearing bomber jackets and jogger pants, “that’s definitely going to influence him.”

Joggers may be exiting stage left (gee, that didn’t last long) but Mr. Moore readily acknowledges that fewer men are wearing classic suits like the one Mr. Jordan modeled. In these digital times, when clothes need to leap out on a cell phone screen to be noticed by scrolling shoppers and offices are downgrading their dress codes, casual, quirkier clothes reign. “We broke out of the ’90s which was all simple and modern but after a while, it was like, ‘How many dark, simple things do you need to own?’” he said. It’s worth noting that this stark minimalism was itself a reaction to the garish ’70s, when brash checked sportcoats and condiment-colored turtlenecks filled GQ’s pages. If there’s one thing four decades in the industry will teach you, it seems, it’s that trends are cyclical. “So now we’re in this moment where the peacock has almost returned,” said Mr. Moore, citing the maximalist fripperies that have recently appeared on GQ’s pages, like Gucci’s Donald Duck-emblazoned sweaters, or Fear of God’s droopy-sleeved, oversize bomber jackets.

A simple style foundation can balance out peacock tendencies, said Mr. Moore, adding, “Get the basics right and then find what it is that makes you special.” That can mean styling a marquee piece without clutter, as GQ demonstrated this past May when it showed Dwayne “the Rock” Johnson wearing Gucci’s cartoon sweater with a pair of inoffensive khakis. Or your signature can be a more of an overall look: You can try “wearing all one color head-to-toe, or wearing an outfit all in one pattern.”

For his part, Mr. Moore is still buying stock in the suit. “Someone once said to me, ‘Oh it’s the death of the suit. What do you think?’ And I love when people make statements like that because it makes me want to celebrate the suit even more,” he said. Yet in our dressed-down times, he sees suits worn with T-shirts edging out ones with ties. He also noted that today’s trousers often have pleats, just like the suits he styled for GQ in the ‘90s.

Has all his experience given Mr. Moore a swami-like ability to predict what trends will hit next? Not quite. “You can think you have a crystal ball and say, ‘Oh, it’s gonna be really tweed,’ or earth tones, or everyone’s going to do mustard, but fashion will usually surprise you.”

Write to Jacob Gallagher at Jacob.Gallagher@wsj.com