What in the world happened to Michael Jordan’s fashion sense?

Marilyn Spiegel, an early ’90s marketing whiz, sat in a meeting full of men discussing Q Scores — a measure of brand familiarity — and wondered, with incredulity, who wants to smell like a basketball player? 

It was 1990, and Michael Jordan, the shining light of the Chicago Bulls, had signed a deal with a cologne company.

They met a few months later at Bigsby & Kruthers, a high-profile Chicago menswear retailer that once dressed His Airness. After Six, the formal-wear company where Spiegel was the vice president of marketing, was shooting Jordan in a tuxedo in the lead-up to prom season. 

For After Six’s promotional shots, stylist Jane Collins dressed Jordan from only the knee up, but a photographer from People magazine, accompanying them for the shoot, was snapping full-body pictures.

Michael Jordan, modeling a line of formal wear, is fitted for a tuxedo with the help of stylist Jane Collins. (Photo by Steve Kagan/The LIFE Images Collection via Getty Images)
Michael Jordan, modeling a line of formal wear, is fitted for a tuxedo with the help of stylist Jane Collins. (Photo by Steve Kagan/The LIFE Images Collection via Getty Images)

When the story was published in December, Spiegel found herself fielding confused callers. “Somebody asked me if it's OK to wear white socks with a tuxedo, that it must be a new fashion thing because Michael had white socks on,” Spiegel told Yahoo Sports over the phone. “And I'd try to explain to the person, ‘No, we didn't expect to shoot him that way.’”

Two years before the first “Be Like Mike” ad debuted, Spiegel — alongside the rest of corporate America — was becoming wise to the full scope of Jordan’s burgeoning influence.

“The Last Dance” has, to the shock of everyone born after 1990, featured Jordan in form-fitting, fashionable clothes. It turns out young Jordan was a style icon. The late author David Halberstam considered him the best-dressed American man next to Cary Grant. Jim Riswold, the former Wieden+Kennedy creative director behind some of Jordan’s most famous Nike commercials, told Yahoo Sports via email that Jordan “never wore the same dress shirt twice.” 

Michael Jordan wears clothes that fit at a golfing event in 1989. (Getty Images)
Michael Jordan wears clothes that fit at a golfing event in 1989. (Getty Images)

There had to be a reason why, in the span of two decades, Jordan went from someone who deeply cared about his image to the guy who inspired a Tumblr called “What the F*** is Michael Jordan Wearing?” To find out why, I asked the designers and marketers who helped Jordan construct his image throughout the ’90s. 

Before the oversized shirts and baggy, washed-out jeans, there was Barbara Bates, who has designed clothes for the likes of Oprah, Steve Harvey and Whitney Houston.

In 1987, Bates fitted then-NBA player Sam Perkins, Jordan’s former teammate at the University of North Carolina. Perkins visited Bates’ studio and invited her to a party that night, where she met Jordan and gave him her card, which he already recognized. Bates’ sister gave one to him at a Bulls game. 

(Bates has repurposed her studio to design PPE masks for healthcare workers, first responders, essential workers and the vulnerable. To donate, click here.)

Barbara Bates hands masks to a police officer at her studio in Chicago. (Courtesy of Barbara Bates)
Barbara Bates hands masks to a police officer at her studio in Chicago. (Courtesy of Barbara Bates)

A few days later, Jordan visited Bates’ apartment — instead of her studio, where she worried a crowd might assemble — and got fitted by her tailor. I was doing lots of exotic [things] like, you know, jackets with studs all over it and colorful blazers,” Bates said. “It was the era of Versace.” Which didn’t fit Jordan. 

Bates custom-made Jordan’s clothes for the next five years, and he never said no to any idea. “Even though he wanted to have a certain look,” she said, “he wasn't going to dictate to you what it is that he wanted.”

“As far as any image he was trying to project, he just wanted whatever was really cool at the time,” Bates said.

Designer Yolanda Braddy, who worked with Jordan on “Space Jam,” put Jordan’s fashion motivations this way in an email to Yahoo Sports: “With MJ being the best on the court, he had to look the best off the court also.” 

As the years passed, Jordan’s physique swelled, courtesy of his trainer, Tim Grover. He used to joke with Grover that he was costing him money in thrown out clothes. One day in the mid-’90s, Grover took Jordan to Burdi Clothing, a boutique designer store in Chicago. 

“He was a super nice guy, super smart. Everyone was in awe of him, including us. He was the most famous person in the world at that time. We would shut the store down when he came in to shop,” Rino Burdi told Yahoo Sports via email. Jordan started buying sweaters and polos from Burdi’s, including some customized looks for “Space Jam,” but they had designs on more. 

Andre Agassi and Michael Jordan greet each other during the 2000 ESPY Awards at MGM Grand Hotel in Las Vegas. (Photo by SGranitz/WireImage)
Andre Agassi and Michael Jordan greet each other during the 2000 ESPY Awards at MGM Grand Hotel in Las Vegas. (Photo by SGranitz/WireImage)

“After he had been shopping with us for a while,” wrote Burdi, “I asked my dad, Alfonso, to take some measurements for a custom suit. Jordan kept insisting that we shouldn't do it, that all of the experiences he had in the past with custom tailoring left him disappointed.”

Rino went ahead anyway, designing a suit based on the measurements of Jordan’s sportswear. 

“When he came out, he was absolutely in love,” Rino said. At the time, baggy, double-breasted Italian suits were en vogue. Rino left extra room for tailoring, so the jacket was extra long and pants were even wider than the edicts of the era suggested. “We tried tailoring a suit the way we thought was proper, but he wanted it back to the original try-on measurements,” said Rino, “and his look was created.” So it was that Jordan serendipitously stumbled into the attire he has adhered to since.

“From the moment he became a custom client, it was a complete collaboration,” Rino said. Together, they’d pick out pieces top-to-bottom that Burdi’s would package into travel-ready garment bags. “He was so much fun to work with because he really did care about how he looked. It wasn't just clothes, it was an identity.”

“He was quite specific about his wardrobe for our CEO Jordan spot,” recalled Riswold. It debuted in 1997, featuring Jordan sneaking out at halftime against the New York Knicks, trading his Air Jordans for brown Oxfords and his jersey for a giant, olive suit. 

Michael Jordan attends a Jordan Brand exhibit in Dallas in February 2010. (Getty Images)
Michael Jordan attends a Jordan Brand exhibit in Dallas in February 2010. (Getty Images)

It’s tempting to theorize about Jordan’s ensuing fall from fashion grace. Maybe his style is a nod to the ’90s that made him. Maybe, considering how reclusive Jordan has been since retirement, he reflexively rejects the self-image he forced himself to live up to as a player. He has become less buttoned up in more than one way. Maybe it’s a giant flex — the endorsement king of the world testing the limits of what he could make cool. That would certainly explain the Hitler mustache.  

Rino Burdi’s simpler explanation sounds closer to the truth. “Some men find their look and that's what they love and feel comfortable in,” Burdi said. “At the end of the day, that's what personal style is all about.

“He told me once that he had always felt self-conscious in his jackets because they felt too short. He was always trying to yank them down. He loved the wider leg pant because it camouflaged how big his shoes were to how skinny his legs were.”

It’s hard to imagine Jordan — who was known for looking good in everything — feeling self-conscious, but despite being one of the world’s most esteemed image-makers, the clothes he eventually settled into serve the same purpose they do for most people: They make him feel good.

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