10 Times Celebrities Wore Absolutely Ridiculous Things

No matter how stylish you are, you’re going to have some misses.

People brick fits every single day. But the moment that got us thinking about some of the other absolutely unhinged attire that celebrities have worn over the years was Usher’s recent viral headwear. The R&B legend has been spotted at a few appearances throughout April 2024 in a hate that resembles a puffer jacket. The beige winter coat for your cranium appears to be a design by Maison Mihara Yasuhiro, who is actually a great designer. Many of you likely know him for his wavy, Converse-inspired footwear. But this design, at least on Usher's head, just comes off as a bit silly. At least the hat might double as a pillow-like cushion if you want to rest your head at a moment’s notice? The viral accessory also made us recall a very important lesson: Just because something was is from a well-known designer brand or handed to you by a stylist does not mean that it will result in a good fit.

While things like MSCHF’s Big Red Boots and those giant hats definitely fit the criteria of being ridiculous, they also became cultural phenomena. They weren’t just one-off instances, so we’re going to take them out of consideration. Things like this iconic Gunna outfit were also taken out of consideration because it reached “so bad it’s good” territory after Rihanna’s Halloween costume.

Yes, before you start thinking, “But what about this one? They forgot that one,” we are well aware that there are hundreds, if not thousands, more examples of celebs rocking bad outfits. We had to curate this thing somehow, so here are 10 that we find particularly memorable.

Depending on how old you are, you might not know who this is. Best known for roles in sitcoms like Sister Sister and movies like You Got Served, the singer/actor’s shine has faded since the late ‘90s and 2000s. But regardless, this ensemble from the 2004 MTV Movie Awards will live on forever in infamy. 

He had to have lost a bet or something, because how else can you be convinced to wear this in public? The clear plastic suit looks sort of like somebody upcycled those see-through bags that bed comforters are sold in. If only Houston waited until 2006 to break this one out. He could have paired it with the “Invisible Woman” Air Force 1s to really go all in on the invisibility theme. Instead, he had to settle for some classic white Air Force 1s. No positives can be drawn from this besides the pure comedy of it all.

We considered leaving this one off the list because it became such a cultural moment that we almost started to like it. But ultimately, Pharrell’s iconic Vivienne Westwood hat that he first wore to the 2014 Grammys deserves to be on this list. It sort of looks like the Sorting Hat from Harry Potter. It sort of looks like the Arby’s logo (the fast food chain even got in on the joke). Either way, it’s particularly goofy. Pharrell can pull off pretty much anything he wears, but this one was just a bit too outlandish. Yes, it’s memorable. That doesn’t necessarily mean it was memorable in a good way. 

Lady Gaga has worn plenty of insane outfits throughout her career, but none have been as wild as her meat dress in 2010. No, it doesn’t just look like meat. She is actually covered in flank steak. Health code violations and disgusting odors aside, it is commendable that they were able to get some beef to drape like a dress and actually look pretty good if you squint hard enough. But then you remember that the pop singer is covered in uncooked meat and can’t help but scrunch your face in disgust. As weird as it all is, props to Gaga for taking the risk and designer Franc Fernandez for bringing it to life. This one will live forever.

Jonathan Anderson is one of the best designers in the world today. We love his work for Loewe and his namesake label, JW Anderson. However, this sweater is just too absurd to actually be worn in public. On the runway, presented with a cohesive collection, it was interesting to see a broken skateboard reinterpreted as an accessory. It just didn’t hit the same when Lil Durk tried to pull this sweater off courtside. It’s hard to take someone seriously when they have a skateboard protruding from their chest. Also, not for nothing, we just can’t imagine this was comfortable. Do we think Lil Durk can kickflip?

As a Sixers fan still coping with the absolutely demoralizing loss we took to the Knicks the other night, getting to laugh at the franchise’s biggest fan is like trying to fix a giant gash with a BandAid. But it’s something, right? 

Anyway, Spike Lee is a fixture at Madison Square Garden during Knicks season and he has been for decades. He’s a certified legend. And he isn’t shy about showing his love by draping himself in tons of orange and blue gear every single night. That’s all good and well. MSG is full of fans in Knicks jerseys for every game. Wearing your team colors is part of the fun of being a sports fan. 

But a puffer Jalen Brunson jersey? I don’t know. The creator responsible for the vest, Jocelyn Hu, does actually make some pretty dope reconstructed gear like these jackets for Allen Iverson and his mother. I still think Lee should have just stuck to a regular Brunson jersey or a John Starks throwback instead. Maybe it’s just the Knicks hate in my heart talking.