Ever since Tyler, The Creator rocked that heather grey Supreme box logo hoodie for his first live TV performance on Late Night with Jimmy Fallon, his legacy as a streetwear god was crystallized. 

Compared to his rap peers, Tyler was never one to dress himself in crazy amounts of high end designer labels. Instead, Tyler has stayed true to his roots as a skate rat who grew up around Fairfax. To this day, all Tyler really needs is a pair of skate shoes, a hat, a T-shirt, and a hoodie. If he ever turns the drip knob up, it usually consists of clothing that he’s made for his own brand, Golf Wang. 

We took a look at Tyler, the Creator’s fits over the years. From the chaotic days of the Odd Future era to his avant-garde Igor phase. Take a look at how Tyler’s style has evolved. 

MTVU Woodie Awards

When: 2011

As Tyler mentions on his 2010 track “Orange Juice,” he’s been so closely aligned with Supreme that he got “Box Logo hoodies and goodies, from buddies that understand that Bastard was buzzing like Woody, so we get it for free.” But what’s important to understand about Tyler’s love for the brand was that it was organic and not fueled by the hype machine. He mentioned that he discovered Supreme simply because it was one of the only skateboard shops in Fairfax, a neighborhood located in Los Angeles.

It’s difficult to imagine where Supreme would be today without Tyler. And it’s even harder to imagine anyone tie-dying a 2011 ‘Kaws’ box logo hoodie like the one Tyler wore to the MTVU Woodie Awards show that same year. Unless you’re John Mayer, an ambitious attempt at tie-dying a rare Supreme box logo will only get you roasted on Grailed when you decide to resell it six months later. 

VGX (Spike Video Game Awards) 2013

When: 2013

Before we go into this incredible fit, we have to lay down this major fact for context. The soundtrack for Grand Theft Auto V was crazy, crazy, fire. That’s because ‘GTA V’ was the first Grand Theft Auto game featuring the waviest artists of our time, who produced exclusive songs for the game’s radio stations. Who could have ever imagined that Rockstar Games would give us the opportunity to run over innocent pedestrians in Los Santos while blasting unreleased Neon Indian or A$AP Rocky songs?  

Although the Spike Video Game Awards didn’t last another year after it was rebranded as “VGX” in 2013, Tyler, the Creator’s live performance of his ‘GTA V’ exclusive banger, “Garbage,” has stood the test of time. With the song being about a drug dealer turning into a murderer, it made sense for Tyler to channel old school mob fashion with a super baggy zoot suit. 

60th Annual Grammy Awards

When: 2018

When Tyler was nominated for the ‘Best Rap Album’ Grammy for the first time in his career, he certainly knew he had to make a statement on the red carpet. Like his album Flower Boy, his fit for Grammy night perfectly captured his maturation as an artist who hasn’t sacrificed his quirkiness. Tyler arrived to the red carpet with white Converse Chuck Taylors and a ‘Golf’ tee, which was more reminiscent of his younger skate rat fashion. However, a Fall/Winter 2018 Supreme wool overcoat paired with a matching baby blue Louis Vuitton scarf, is a dapper fit for the biggest night in music. And a white Soviet Union-era Ushanka is a statement piece that ties this cozy fit together.  

"Dr. Seuss' The Grinch" Premiere

When: 2018

The popularity of Tyler’s brand Golf Wang can certainly be attributed to his own taste. He wears an eye-catching floral puffer—reminiscent of grandma’s couch—that's balanced out with khaki trousers and a bucket hat. A leather Golf Wang clutch, worn as a side bag, ties it all together.  

Lollapalooza 2018

When: 2018

Here’s another bold Golf Wang fit that suits Tyler’s explosive personality. This thermal image of an atom bomb printed onto a button-up shirt is pure heat.

French Open 2019

When: 2019

There’s something extremely comforting about looking at Tyler’s game day fit for the French Open this year. Although it’s difficult to put my finger on it, it definitely has to do with that pastel pink cardigan draped around his shoulders. One of the standout pieces from GOLF le FLEUR’s collaboration with Lacoste, a cardigan that looks like it was made from cotton candy is just too damn cozy.

Biking In Los Angeles

When: 2019

“Me and Slater just hit a curb/Bunny hop, zoning out, listening to N.E.R.D.” Although Tyler is known for skating, he professed his love for riding BMX bikes strongly on his second album Wolf. Although the bike Tyler’s riding probably isn’t the infamous “Slater,” it’s a “Block Flyer” BMX bike from the Long Beach company SE Bikes. Tyler keeps this biking fit simple. An all white Carhartt WIP shirt is nicely complemented by different shades of brown from a Stray Rats hat, a matching pair of brown slacks, and light brown Converse GOLF le FLEUR's. 

Roc 96 x Madeworn Barneys Launch 

When: 2017

Tyler always looks great in pink. Here he is with a pink Golf Wang cap to match a striped pink Supreme polo from Spring/Summer 2017.

The Thurnis Haley Fits 

When: 2011

Thurnis Haley, Tyler, the Creator’s 53-year-old golf loving alter ego, embodies dad fashion at its finest. Always wearing a blue Kangol, an oversized polo shirt, and a tacky knit sweater vest, Thurnis Haley puts together the perfect fit for anyone who loves washing golf balls inside a laundromat and partaking in illegal substances.

MTV Video Music Awards 2011

When: 2011

A defining moment for Tyler, the Creator’s career was when he won his first award at the 2011 MTV Video Music Awards for Best New Artist. When Tyler won the Moonman, he ran up on stage with a tie dye ‘Tron Cat’ tee and a leopard Supreme camp cap from Fall/Winter 2011. Although his acceptance speech wasn’t the best, his fit certainly inspired legions of teenagers to only dress in Supreme and Odd Future gear for months to come.

Coachella Music Festival 2017

When: 2017

On his song “Bastard” Tyler says “I wear green hats because I’m fortunately lucky.” That bar makes absolutely no sense, but I guess it means he loves the color green. This fit from Coachella 2017 is a great example of that. A green Supreme striped collar terry polo from Spring/Summer 2017 matches perfectly with his shorts and Golf Wang snapback.

Coachella Music Festival 2015

When: 2015

This blue Golf Wang button up that Tyler wore on the cover of Cherry Bomb is easily one of the most iconic shirts he’s ever made. This Guy Fieri phase will be missed.

Chicken And Waffles Fit

When: 2015

We just love this fit because of Tyler’s excellent food choice. There’s nothing else here that would make us include this on our list. We hope he kept that magazine clean while he was eating.

Governors Ball Music Festival 2019

When: 2019

Tyler’s latest persona, Igor, marks a major shift in his music and his personal style. Never before has Tyler opted to trade in graphic tees and skate shoes for a well-tailored suit and hard bottoms. Yet, even with a ridiculous Andy Warhol wig, it works. Whether it was Supreme or Odd Future merch, the Igor look further shows how Tyler always thinks outside the box when it comes to his fits.

Golf Pride World Wide Tee

When: 2015

One of Golf Wang’s most controversial releases was the “Golf Pride World Wide” tee from the brand’s Spring/Summer 2015 collection. The shirt took the Celtic Cross, a hate symbol used by white supremacists, and printed it in a rainbow colorway. Shortly after revealing the design in the brand’s lookbook that season, Tyler explained that he was trying to take the power away from the hate symbol by turning it into a symbol for LGBTQ pride. It was a risky but memorable move by Tyler.