Man on the Moon: Some of Kid Cudi's Most Memorable Outfits

Image via Getty/Randy Holmes

When: February 2009

For the Fall 2009 Michael Bastian fashion show, Cudi caught up with Kanye wearing his uniform at the time: leather moto jacket over a grey hoodie, his Jesus piece necklace, simple black T-shirt, a Louis Vuitton keychain wallet, skinny jeans, and Jordan 3s. This was shortly before Cudi would star in the HBO Series How to Make It in America as Domingo, helping secure his spot as a low-key style icon. —Aria Hughes

When: May 2009

This look is quintessential Cudi from the A Kid Named Cudi and Man on the Moon era. If you saw Cudi out and about, chances are he was wearing something like this. The big glasses, the Bape T-shirt layered with a black leather biker jacket, and Air Jordan retros (usually 3s or 4s) were all staples in his wardrobe. The jewelry on display here is like a time capsule back to the late Aughts too. Check out the gold Jesus piece and bright green Ambush POW! chain. And that KAWS Companion zipper pull, so subtle. Saying this fit influenced how thousands of kids dressed at the time might be an understatement. —Mike DeStefano

When: September 2009

If you’re a Kid Cudi fan then you have certainly read about his affinity for Bape by now. Depending on your age, Cudder may have even been your introduction to the iconic Japanese streetwear label. Before Cudi's popularity exploded after the success of “Day N Nite,” the Cleveland transplant was peddling Shark hoodies at the Bape store in New York’s SoHo neighborhood. So, the fact he was able to attend his first MTV VMAs red carpet just a few years later rocking his own Bape T-shirt collab emblazoned with himself Baby Milo’d on the chest is pretty impressive to say the least. The “Bred” Air Jordan 4s, a pair frequently laced up by him at the time, the gold Jesus piece, raw indigo denim, and black G-Shock to complete the look—and these pieces were probably in your Karmaloop cart back back in the day. I’m sure some of you are feeling a bit nostalgic seeing a fit like this in 2020. —Mike DeStefano

When: March 2013

This is truly a Kid Cudi fit. Thick as hell yellow glasses, a baseball cap, a simple pair of Vans, a vintage Simpsons T-shirt, and a striped red cardigan to top it all off. When Kid Cudi came on Jimmy Kimmel Live in 2013, he performed “Immortal” and “Just What I Am” off of his third studio album Indicud. —Lei Takanashi

When: April 2014

Crop Cudi was certainly a moment. The rapper took the stage during his Coachella set in 2014 rocking a red fleece crop top, cut off denim shorts, and immediately had the internet talking. In the same way Lil Wayne’s animal print leggings or Kanye West’s Celine blouse had before, Cudi’s crop top received praise and critique. But if you ask us, Cudi certainly pulled it off like few would be able to, and it still remains one of his most memorable looks to date. The Bape boxers and “Infrared 23” Air Jordan 2, while an unconventional colorway, were a nice nod back to Cudi’s Man on the Moon era too. —Mike DeStefano

When: June 2018

June 21, 2018 marks a monumental day in fashion history. It’s the day Virgil Abloh, the house’s first Black designer, presented his debut collection for Louis Vuitton on the runway during Paris Fashion Week. And Abloh made sure that he kicked off his era of LV with some of his best friends. Kanye West sat front row and the two had an emotional embrace as Abloh made his final walk. Songs like West’s ”I Thought About Killing You" played over the speakers. The likes of Travis Scott, Takashi Murakami, and Don C were in attendance. ASAP Nast and Playboi Carti walked in the show. So did Cudi, wearing slouchy trousers, a hoodie, and a cream-colored trench coat. 

In an interview with Jaden Smith for V Magazine in 2018, Cudi said, “It was an incredible experience to be part of that—a monumental moment. It makes me excited for fashion. He’s doing groundbreaking things.”—Mike DeStefano

When: June 2018

It’s clear that Kid Cudi loves vintage graphic tees. For Kim Jones’ Spring 2019 Dior runway show, Kid Cudi arrived sporting a vintage In Living Color “Homey The Clown” T-shirt underneath a tailored blazer. However, the real flex in this fit were the sneakers: Off-White x Converse Chuck Taylors signed by Virgil Abloh himself. Cudi’s relationship with Abloh runs deep. The designer even made the album cover for Cudi’s 2012 project Wzrd. “No matter if he was working with Kanye or he was doing his own thing, he’s always been ahead of the curve,” Cudi told Complex for our 2019 cover story. “I remember when he designed my album cover for Wzrd. That was way before anybody was even on Virgil. I knew he was this really dope designer, so I was just like, ‘Yo, dude, can you design my album for me?’” —Lei Takanashi

When: January 2019

When Kid Cudi pulled up to Louis Vuitton’s Fall 2019 runway show, he came in a fit that really nailed the Micheal Jackson-inspired theme that Virgil Abloh was going for with his second collection. Yes, Cudder wore a single bedazzled red glove with more stones than an Infinity Gauntlet. He paired this glove with a red hoodie, a tough black leather trench coat, Louis Vuitton Millionaire sunglasses, and an LV Soft Trunk bag draped across his chest. Surprisingly, Cudi chose to wear a humble pair of clean white Adidas Superstars to Paris Fashion Week. But it unintentionally blended well with that white throw-up by Lewy BTM behind him. For a better look at this glove, just check out this great portrait that Gunner Stahl took of him—who also happens to be one of Cudi’s biggest style fans. “Honestly, I'll take a look on my computer and try to find every Cudi outfit from 2010 or 2011,” Stahl told us in an interview. —Lei Takanashi

When: November 2019

Man, although ComplexLand is ill, we truly cannot wait to bring all our readers back to ComplexCon again because of magical moments like this one right here. There’s a lot to break down in this fit right here. First of all, Kid Cudi didn’t just headline ComplexCon Long Beach wearing this fine Louis Vuitton cardigan. He also rocked an exclusive Human Made x Billionaire Boys Club T-shirt that was only available at the event—today, it’s still a coveted item being resold on sites like Grailed. Reminiscing on the event itself, who can ever forget Kid Cudi’s performance at ComplexCon? You had Timothée Chalamet opening the set by narrating Common’s intro from Man on the Moon, followed up by Pusha T coming on stage to perform “Feel The Love” off Kids See Ghosts. It was a set filled with classics and legendary moments like this would only happen at ComplexCon. —Lei Takanashi

When: March 2020

Kid Cudi might be one of the only rappers who can rock Virgil Abloh’s Louis Vuitton pieces so effortlessly. For the red carpet premiere of the third season of Westworld, which Kid Cudi played a minor role in, he came wearing one of Abloh’s jackets from his Fall 2019 collection. He paired this statement piece with some black leather pants, hi-top sneakers, and an iced out chain featuring Takashi Murakami’s “Kiki” character. Cudder’s chain was designed by Ben Baller and the “Kiki” piece was made out of rubies, diamonds, and pink sapphires on an 18K gold pendant. It was gifted to Cudi for his 36th birthday. —Lei Takanashi