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When he first came onto the scene, Tyler the Creator was always hanging out on Fairfax wearing head to toe Supreme with Vans Authentics or Old Skools. This, of course, was before they were as popular as they have become by today’s standards.

His footwear game then wasn’t even about hype or signature exclusives. Inline offerings, like the generic navy or black offerings, were not only satisfactory to his personal taste, but they were also versatile enough to wear with the rest of his usually colorful wardrobe selection.

Today, his style isn’t much different, except for the fact that he’s switched over to Converse, where he’s had several head-turning collections of his Golf le Fleur line that have appeared in an assortment of vibrant colorways. Converse’s key initiative was pushing the One Star silhouette and they’ve essentially made Tyler the face of their campaign, letting him pursue his own creativity, while even offering general releases of the silhouette that subtly mimic his reputable style.

Vans On and They Look Like Sneakers

Vans were Tyler the Creator’s favorite shoe at one point as he made plenty of use out of their versatility to complement his skate style that resembles that of any Fairfax native. Unlike most hip-hop artists, Tyler doesn’t have to flaunt the latest sneaker collaborations to prove he has style. He’s already wearing plenty of Supreme as it is to demonstrate that. Aside from his numerous Golf Wang collaborations with Vans Syndicate, he was only really repping the Old Skool and Authentic silhouettes – primarily in the navy or black colorways. What this does is it allows you to freestyle the rest of your wardrobe, whether that be vibrant color schemes, box logo hoodies, oversized polos, and even above the knee shorts. And like anyone who’s actually skating, you’re not too worried about keeping your shoes clean, as a basic pair of Vans are fairly simple to come by.

Basics aside, Tyler the Creator has also been heavily involved from the design perspective with Vans, having several collaborations with his Golf Wang and Odd Future collections. He was also breaking grounds when it came to thrashing grailed essentials like the Supreme x Vans Campbell’s Authentics. And not only was he not worried about the condition of his kicks, but he also wasn’t worried about mixing patterns on his apparel that shouldn’t “go together” long before it was a mainstream tactic in modern day fashion design.

The flower inspiration behind Tyler the Creator's Golf le Fleur x Converse collection is finally evident. The shades of red and pink add some nice contrast to the otherwise fairly neutral look.
The flower inspiration behind Tyler the Creator’s Golf le Fleur x Converse collection is finally evident. The shades of red and pink add some nice contrast to the otherwise fairly neutral look.
Tyler the Creator was wearing Thrasher sweatshirts before it was cool, but a pair of Vans Old Skools and a Supreme cap really complement the Fairfax local look.
Tyler the Creator was wearing Thrasher sweatshirts before it was cool, but a pair of Vans Old Skools and a Supreme cap really complement the Fairfax local look.
G is for matching green hats with green pants. Throw in a pair of checkered Vans and your look is money.
G is for matching green hats with green pants. Throw in a pair of checkered Vans and your look is money.
Neutral toned tees and cutoffs with Vans Old Skools can be a summer essential uniform, while just as easily carrying into the fall season for those experiencing an Indian summer.
Neutral toned tees and cutoffs with Vans Old Skools can be a summer essential uniform, while just as easily carrying into the fall season for those experiencing an Indian summer.
The cool thing about Vans Authentics is that nobody really cares if they match your tee, pants, and hat accordingly. They're also a timeless essential that's always on trend.
The cool thing about Vans Authentics is that nobody really cares if they match your tee, pants, and hat accordingly. They’re also a timeless essential that’s always on trend.
Graphic tees jazz up a t-shirt and pants combo any day of the week. Vice versa for Frank Ocean.
Graphic tees jazz up a t-shirt and pants combo any day of the week. Vice versa for Frank Ocean.
A checkered pair of Old Skools checks off all the requirements for today's streetwear essentials.
A checkered pair of Old Skools checks off all the requirements for today’s streetwear essentials.
The future for fashion looks odd, but Tyler the Creator doesn't look too worried about it.
The future for fashion looks odd, but Tyler the Creator doesn’t look too worried about it.
When you can wear the same pair of Vans that you wore yesterday, you can get everybody jumping with excitement about what shirt you're gonna break out this weekend.
When you can wear the same pair of Vans that you wore yesterday, you can get everybody jumping with excitement about what shirt you’re gonna break out this weekend.
A blank canvas for a Warhol approved wardrobe.
A blank canvas for a Warhol approved wardrobe.

Pros and Cons

Over the past couple of years, Tyler the Creator has moved on from his partnership with Vans and onto a deal with Converse that has allowed his creativity to flourish and match his style accordingly. Next to complementing his own wardrobe, his Golf le Fleur collaborations with Converse have also become a mainstay in plenty of other fashion enthusiasts with skate style. Tyler the Creator wears a lot of Supreme apparel – Fact. But if you’re just a micro-second short of missing the online Thursday morning drops or don’t have time to wait in line on Fairfax all day, how would you get a similar look? Fortunately, the Supreme is a roots skateboarding brand, so there are a few other core skate and even higher end skateboarding brands like Carhartt WIP, Pop Trading Co, and Noah that are all making similar silhouettes. This mostly entails wider legged chinos, long-sleeve polos, boxy hoodies, and coaches jackets.

Another aspect of Tyler the Creator’s style that makes it so alluring is his consistency of breaking the norm and the rules of fashion – literally. He actually wore white Converse on the red carpet at the Grammys. Does he care about the “rules?” Probably not. And that’s what makes his own style that much more unique. He’s also known for wearing pastel tees, polos and button-ups when it’s not even spring. On that note, it might slightly help that he lives in Southern California.

Lettering in having timeless style.
Lettering in having timeless style.
Pastels, prints, and Converse One Stars are the key ingredients to creating a street ready look.
Pastels, prints, and Converse One Stars are the key ingredients to creating a street ready look.
Wondering how to dress up sneakers. Check out Tyler's pairing of dark chinos, light hued over coat, and LV monogram scarf.
Wondering how to dress up sneakers. Check out Tyler’s pairing of dark chinos, light-hued overcoat, and LV monogram scarf.
Red carpet ready. Rules broken.
Red carpet ready. Rules broken.
Walk on the wild side. Rep red. Wear Converse One Stars.
Sophisticated tailoring meets colorful comfort.
Sophisticated tailoring meets colorful comfort.
Tyler's been doing it before it was popular, but prep is back and so is pink.
Tyler’s been doing it before it was popular, but prep is back and so is pink.
Flower power with plenty of ammo leftover.
Flower power with plenty of ammo leftover.
You can easily get the LA look with cropped denim and pastel One Stars. Don't wanna buy raw hemmed jeans? Grab some scissors.
You can easily get the LA look with cropped denim and pastel One Stars. Don’t wanna buy raw hemmed jeans? Grab some scissors.

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