Tyler, The Creator’s Latest Preppy Look Reflects Hip-Hop’s Endless Style Evolution

Tyler makes cardigans cool again.

Tyler, the Creator smiles and points at a fan on the red carpet.

Image: Getty

Tyler, the Creator has long been renowned as a subversive style icon, but his latest look is further proof that he remains a pioneer of troublemaking trends that challenge the established traditions of fashion and music alike.

From his first forays into fashion as part of Odd Future (the generation-defining rap collective that once included Earl Sweatshirt, Domo Genesis and even Frank Ocean) sporting bright, colourful turns on 2010s streetwear, Tyler has always made his style a central part of his brand, considering his style and his music to be two sides of one broader artistic project. He’s also got impeccable taste in cars and watches to boot.

Over the weekend, while visiting cult skate brand Supreme’s brand-new LA flagship store, he wore a skate-prep crossover look that proved his style evolution is far from over. The centrepiece of the outfit was a bright orange v-neck knit, a silhouette that’s made a rapid return to style in the last few seasons.

Layering this with a button-down white Oxford shirt, a statement tartan tie, and a black puffer, his bottom half was decked out with light-wash jeans and classic loafers, finished with a grey wool cap.

Tyler and fellow rapper A$AP Rocky pose for the cameras at the Supreme LA store. Image: @atibaphoto

Not only is this a killer look that perfectly matches Tyler’s idiosyncratic personality, but it represents a subversive streak in his sense of style that pushes the boundaries of fashion and hip-hop alike.

By taking a preppy look – the ultimate aesthetic of American aspiration, espoused by the upper middle classes and so-called “Old Money” that represent the US establishment, and interweaving it with the skater aesthetic and gaudy colours that have come to define his look in years gone by, he announces himself and the hip-hop world more broadly as the new fashion establishment.

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Similarly, you can read this the other way: by elevating the skater style of his early years with heavy knits, pressed shirts, and statement ties, he puts a new spin on hip-hop’s long-established style stereotypes. Swapping out the street-style aesthetic that came to define the genre in its early years and long since, replacing it with an aesthetic much more suited to the golf course or country club, he challenges the assumptions and expectations of what a rapper can or should look like.

Tyler later that evening. Image: Getty

It’s also fitting that he’s wearing such an outfit at Supreme. Tyler and the rest of his Odd Future companions have long been associated with Supreme (with Supreme reportedly supplying some of the gang with free clothes at the height of OF’s fame) and did much to popularise the brand in the mainstream in the early 2010s.

It’s a reminder of where Tyler’s come from – both artistically and stylistically – as well as his enduring status as a tastemaker. He has always been a troublemaker but this latest look proves that his rebellious days are far from over, and we’re here for it.