When it comes to the basketball court, there’s no question that Michael Jordan is the GOAT.

Fashion-wise, His Airness has always been quite the enigma. For years, not-so-stylish cargo jeans and bucket hats have been staples for the greatest basketball player of all time, and yet retro Air Jordans remain some of the most fashion-forward footwear both on the court and off.

So, how does someone so influential in street culture don such questionable fits year after year, and get away with it? Maybe it’s the fact that Jordan wears what he wants without being influenced by trends that gives him an air of style invincibility. Mike has been rocking baggy jeans and ill-fitting blazers since the ‘90s, and he isn’t about to change. He’s the certified GOAT of IDGAF fashion, so here are ten of his greatest (or worst, depending on where you’re coming from) outfits of all time.

Bootcut jeans so big, you may as well walk barefoot

If there is one feature of Michael Jordan’s wardrobe that has been consistently subpar the longest, it’s his odd taste in denim. In college, Jordan sported some better-fitting trousers; but as the years progressed, his denim got baggier, and not in a good way.  Incredibly, Jordan wore the above bootcut jeans over a pair of sneakers that weren’t available to the public at the time — the Air Jordan 11 Low. These shoes hit shelves in 2014, almost 20 years after Jordan first rocked them. Sadly, the terrible denim distracted from what is likely the earliest #TeamEarly flex of all time.

It’s gotta be the socks

Michael Jordan was the ultimate on-court trend setter when it came to sneakers, jerseys and even his socks. When Jordan debuted the Air Jordan 12s in Japan during a promotional tour, he wore very low-cut socks, which helped highlight the shoe. As the 1996/97 season kicked off, however, Jordan began wearing incredibly long tube socks pushed all the way down. Jordan still managed to pull off the look, but the socks clearly became the focal point of the fit. A possible explanation is that the Jordan 12 was causing him discomfort with no-show socks.

Getting buckets in bucket hats

If Fashionista.com is right, and bucket hats really were a thing last year, Michael Jordan should get all the credit for starting that trend. Jordan has had a weird obsession with bucket hats for years given their excellent, 360-degree brim coverage for outdoor activities like golf and chilling with world famous celebrities.

The infamous Canadian ’Tux

Up until this point, the GOAT was actually pretty fashionable off the court. Dating back to his college days at UNC through the early part of his career, Jordan wore mostly fitted clothing and fashionable suits. That all came to a screeching halt when Jordan threw out the first pitch at the 1993 American League Championship Series. The denim shirt/denim pant look (aka Canadian Tuxedo) is a tough one to pull off. It can be done, as Aaron Rodgers proved here, but Jordan’s suede shoes ruined any chance of it being done right.

MJ enters the Matrix

As popular as oversized silhouettes are nowadays, the mid 2000s took things to a whole new level. Michael Jordan, of course, took full advantage of this when he was a judge in the 2007 NBA All-Star slam dunk competition. Jordan wore his go-to baggy jeans and added a twist: an oversized 4-button black leather blazer. When you’re wearing a black leather blazer, you’re constantly toeing the line between Matrix cosplayer and badass action movie star. When done right, a black leather jacket paired with denim is an unbeatable fit. This was not one of those times.

When your cargo shorts get you banned

During Michael Jordan’s basketball career sneakers such as the Nike Air Jordan 1 and Air Jordan 11 were banned by the League because they broke NBA team color guidelines. Similarly, the cargo pants Jordan donned at a Miami golf course in 2012 were just as controversial as his illegal footwear, reportedly getting him banned from the golf course. Sadly, these pants never gained the same allure as his Jordan 1s or 11s.

Draped in velvet

If there’s one thing you can’t say about Michael Jordan, it’s that he didn’t at least try to mix up his style, like when he thought it would be a good idea to wear a velvet blazer. The velvet blazer is another look that, when done correctly, signifies sophistication and a daring spirit. Seinfeld’s George Costanza famously draped himself in velvet, because his girlfriend said looks weren’t that important to her. It didn’t really work then, and it didn’t when MJ did it either.

Derby Day fit gone wrong

Was that a storefront awning or a suit? The Kentucky Derby has always been an opportunity for attendees to get dressed to the nines, while rubbing elbows with aristocrats and enjoying one of the richest traditions in American sports history. The key to pulling off a dope derby look is to dress sophisticated, with a touch of whimsy. At least Michael Jordan got the whimsy part right.

The trademark hoop earring

“Don’t Michael Jordan still got his hoop earring in?” Rapped Drake back in 2013. The answer today is still yes. It doesn’t matter what decade it is, that gold earring is staying in Jordan's left ear lobe whether it is trending or not. And while earrings are certainly a fashion-forward accessory for men nowadays, Michael Jordan’s could use some updating. Call it trademark, call it old school, Michael Jordan isn’t taking that hoop earring out for anyone. You have to respect it.

Ultra Star hair care

Of all the looks Jordan is known for, one of the best is his shaved head. That’s what makes this Ultra Star hair care commercial so bizarre. Featuring Coming to America actress Shari Headley, Jordan sings and promotes a product for men’s hair care. The only problem is that Jordan didn’t have much hair back then, and he had even less going forward. It wasn’t a bad thing that he shaved his head, it’s just strange that Jordan would promote a product he had literally no use for.

What To Read Next