A collage of Tyler the Creator's best outfits.
Photo illustration by Kaushik Kalidindi for Okayplayer.

Fits & Flows; How Tyler, the Creator Challenges Music and Fashion

We’re watching and celebrating the progression of Tyler, the Creator as an artist, musician, and fashion icon.

With a host of studio albums, merchandise, and visual projects, Tyler, the Creator possesses a unique capability to generate original masterpieces. His ability to tell a story through his music has been evident since his debut, and he has continued to use multi-layered storytelling in all aspects of his creations. Along with his lyrical abilities, his personal style has evolved with unique synchronicity to his music. No matter which fashion era of Tyler’s is your favorite, each one has a distinct place in his musical creations.

Tyler, the Creator began his career in the late 2000s as one of the founding members of the alternative hip-hop group Odd Future. He released his solo mixtape, Bastard, in 2009, a collection of gritty, coarse, and offensive lyrics. His style at the time reflected his lyrics, with many of his clothing pieces being brightly colored, mismatched, and covered in profanity.

A photo illustration showing Tyler, the Creator in an oversized Odd Future shirt wearing a boot. Photo illustration by Kaushik Kalidindi for Okayplayer.

The New York City-based skatewear brand, Supreme, was a significant component of his early clothing ensembles. Utilizing their unique hats, hoodies, and t-shirts, Tyler helped to popularize the brand amongst his fans, earning him a partnership. Because of this, teenagers all over the world were running to stores in search of clothes like his. Tyler launched his own clothing line, Golf Wang, in 2011, releasing seasonal collections of wacky graphic tees, collared button-ups, hoodies, and accessories that made up his signature style. The release of his first studio album, Goblin, accompanied the release of the clothing line, perfectly allowing consumers to take on the persona he presented entirely. Both Bastard and Goblin helped to foster a specific sense of style that fans took notice of and tried their best to replicate.

2013 brought the release of Tyler’s second studio album, Wolf. Arguably one of his most structured albums, Wolf is composed of several characters with individual stories and conflicts outside of Tyler, himself. The album flaunts a blend of childlike and macabre themes, with the dynamics portrayed in the characters and the visuals for the album. The music video for his song, “IFHY” ft. Pharell, perfectly conveys this aesthetic, with vivid colors and dollhouse settings and makeup. Wolf is also the first of Tyler’s albums to convey new environments in his storytelling, both visually and lyrically. This new venture marks the start of a pattern he exhibits in later projects.

In the visuals for the album, Tyler can be seen almost exclusively wearing Golf Wang, which is the beginning of the brand’s exposure to his music. Golf Wang’s 2013/2014 collections featured more striped shirts and polos (a Tyler staple), five-panel hats, and graphic t-shirts. Around this time, Tyler was often seen dressed in head-to-toe Golf Wang, proudly wearing his own branded creations. In 2013, Tyler also announced a collaboration with Vans, an opportunity for him to imprint his own style onto the classic Old Skool silhouette. This collaboration was the beginning of Tyler’s entry into fashion collaborations that would be more frequent in his career as time went on.

A photo illustration of Tyler the Creator on a yellow background in a blue shirt. Photo illustration by Kaushik Kalidindi for Okayplayer.

Tyler’s 2015 studio album, Cherry Bomb, is his most experimental album in terms of his music and overall sound. To avoid being pigeonholed as a rap artist, Tyler produced an album that transitions from piercing dissonance to euphonious melodies and vocals. The visuals in the album also mimic these themes, foreshadowing an upcoming shift in his aesthetic.

Cherry Bomb featured an array of bright colors in the clothes, similar to his last albums, but this time, they were directed in a more intentional direction. The video for his song, “DEATHCAMP”, uses a desert background to give focus to the colors and patterns on the clothes. The iconic blue and yellow flame pattern was used throughout the video and the album, another widely known symbol of Tyler’s mark on fashion. Cherry Bomb also signals the beginning of Tyler’s turn into preppy fashion. By using pastel colors for clothing, Tyler almost creates a dreamscape in his music videos. In contrast to his past videos, Tyler’s use of colorful outfits on Cherry Bomb feels more intentional and calculated.

A photo illustration of Tyler the Creator in a sweater and patterned pants against an organe background. Photo illustration by Kaushik Kalidindi for Okayplayer.

The release of Tyler’s fourth album, Flower Boy, introduced a new aesthetic to his music and his fans. The album cover for Flower Boy is often the most recognizable of his works because of its drastic shift from what fans were accustomed to seeing from him.

Taking the title literally, we see Tyler implementing more florals into his style and merchandise. The Golf Wang collections released around this time also saw a theme change, with patterned cardigans, vests, and slacks joining the usual clothing lineup. Tyler continued his collaborations through this time, most popularly with Converse being at the forefront. The collection was dropped in 2017 following a departure from Vans while also opening the floodgates for more collaborations with the brand to come. During his Flower Boy era, Tyler leaned more into retro fashion, popularizing a style his fans were excited to recreate.

Photo illustration of Tyler the Creator in his Igor outfit. Photo illustration by Kaushik Kalidindi for Okayplayer.

Tyler’s fifth album, Igor, marked a major shift in Tyler’s fashion and overall music evolution. Bringing a new sound to the table entirely, Tyler was no longer the same artist that the world saw at his debut. He experimented with more soulful melodies and paired them with heartbreaking lyrics.

In addition to sound experimentation, he introduced his fans and the world to a new alter-ego. Sporting a short blonde wig, pastel suits, and dark sunglasses, “Igor” had made his entrance. Along with his onstage persona, his street style turned towards more quality, polished pieces. He began incorporating loafers, Ushankas, and higher-level accessories into his wardrobe. By blending elements of his past and present styles, Tyler was able to branch out in an unpredictable direction.

Photo illustration of Tyler the Creator with lugae and the classic Call Me if You Get Lost winter hat. Photo illustration by Kaushik Kalidindi for Okayplayer.

His most recent album, Call Me if You Get Lost, was released in the early summer of 2021 and, as expected, brought forth a new aesthetic and alter ego for Tyler. Referred to as “Tyler Baudelaire” on the album, Tyler explores themes of love, travel, and gratitude through more experiments with sound, samples, and lyricism. His talent in creative direction also shines through, exemplified in his attention to detail, color, and stylistic choices.

The rollout for the album served as a harbinger of the direction in which his style was going. CMIYGL was the beginning of Tyler’s fashion making a complete 180-degree pivot from where he began. Instead of sporting graphic tees and tie-dye patterns, Tyler stepped out in high-quality furs, silk scarves, and suits. The biggest thing to come from this wardrobe change was the revival of a subsect of Golf Wang, Golf Le Fleur, which he reintroduced as a luxury brand. Golf Le Fleur originally started as his Converse collaboration in 2016, but Tyler’s new style led him to change the brand’s direction completely. In this new incarnation, Golf Le Fleur transformed into a luxury label delivering higher quality items, such as mohair sweaters, personal fragrances, nail polishes, and Globetrotter trunks. Tyler’s new creations garnered him recognition for his eccentric style, and firmly entrenched him as a bold and fearless fashion trailblazer.

Tyler’s recent moves in the fashion world have been focused on expanding the range of his clothing brands. His third Golf Wang store just opened in London, making his products more accessible to global consumers. Additionally, the new clothing line for Tyler’s Le Fleur x Lacoste collaboration was released recently, boasting a new assortment of high-end pieces.

We rarely see an artist undergo so much growth in all aspects of their public image in such an intricate way. Whether you prefer the earlier or present styles of Tyler, the Creator, there is no denying that his originality has been a huge part of his evolution as an artist and fashion icon.