On July 21, Tyler, the Creator surprised fans with the release of his ninth album Don’t Tap the Glass. For his latest era, he shifted his style to honor hip-hop’s wardrobe of the late ’80s and ’90s complete with thick gold chains, leather pants, and giant sunglasses.
This isn’t the first time we have seen Tyler take his style in a new direction for his latest project. In fact, it’s pretty easy to pinpoint the shift each time. He’s slowly morphed from the skate, streetwear kid who mainly wears bold graphic T-shirts and destroyed Vans to a more preppier look that we see today. Along the way, Tyler hasn’t fully abandoned his playful side. He’s always wearing wild prints and bright colors, he just does it in a new way with each project.
With the arrival of Tyler’s latest album, we decided to take a look back at his style metamorphosis from album-to-album.
Album Released: 2011
Signature Items: Odd Future doughnut T-shirt and Supreme Box Logos
When Tyler first broke onto the scene, he was polarizing to say the least. Some listeners instantly fell in love with his vulgar lyrics and shocking visuals that accompanied his debut album. Others weren’t immediately eager to support the West Coast rapper’s violent verses and roach-eating antics. But the fans that did co-sign from day one made sure to make their voices heard, which resulted in Tyler, the Creator taking home the VMA for Best New Artist back in 2011 (the award was fan voted). To this day, Tyler fans will certainly remember his acceptance fit. Tyler showed up to MTV’s iconic award show the same way he used to show up to spend the day hanging out with his buddies on Fairfax Avenue. At the beginning of his career he dressed like a skater and wore a colorful graphic T-shirt, usually covered in cats or doughnuts to rep his Odd Future crew, simple pair of jeans or cut-off shorts, white tube socks, and low top Vans on feet. Of course, there was always a piece from Supreme in the equation too. Box logo hoodies, camp caps, T-shirts, Tyler repped it all. It’s been said before, but Supreme definitely got a boost and was introduced to a whole new generation thanks to Tyler’s major co-sign during his come up.
Album Released: 2013
Signature Items: Striped Golf T-shirts and thrashed Vans Old Skools
By the 2013, when Tyler released his second album Wolf, his wardrobe hadn’t changed drastically just yet. It was still very skate-inspired. It was still made up of brightly-colored items, something that has remained a signature of Tyler’s wardrobe. But by this point, there was a bit more of an emphasis on Golf, Tyler’s streetwear line that launched in 2011. This fit is a perfect example of what you could expect to see the rapper wearing: a striped Golf T-shirt, Golf logo strapback cap, shorts, and a thrashed pair of Vans Old Skools. Tyler was rocking Vans so heavily that he would release multiple collabs with the brand from 2013 to 2016. Tyler had cultivated a loyal fanbase that followed his every move and this type of outfit became their uniform.
Album Released: 2015
Signature Items: Golf “Flog Gnaw Motors” flame print button-up
Like the music on the album, Tyler’s style during the Cherry Bomb era also indicates a slow and steady maturation into a new aesthetic. The eye-catching prints and colors are still present, but on new silhouettes beyond the usual T-shirts or hoodies. Rugby shirts and vacation shirts covered in bold prints become a mainstay in his rotation. One of the most memorable was the flame print showcased on the cover of Cherry Bomb. The blue pieces covered in orange and yellow flames have gone on to become a signature offering for Golf. Items like puffer coats and shorts bearing the print would debut in future collections from the brand. At this point, Tyler still hadn’t fully abandoned his love for polarizing graphics tees and bubblegum-colored Vans sneakers. He merely just introduced another look into his arsenal.
Album Released: 2017
Signature Items: Converse Golf Le Fleur sneakers, floral prints, and quarter-zip sweaters
Tyler was well-established by the time Flower Boy released in 2017, but his fourth studio album was arguably his most well-received by critics up to that point. It even resulted in a Grammy nomination for Best Rap Album. The raucous and loud Tyler was still there on tracks like “Who Dat Boy,” but he also introduced a more introspective and somber side of himself on songs like “Garden Shed” and “911/Mr. Lonely” that were easier for mainstream listeners to digest. Tyler’s sound was evolving beyond his “Yonkers” years and his wardrobe was too. Neon polka dots were replaced with floral prints. Hoodies were replaced with wool sweater vests. Cut-off jean shorts were supplanted by tailored trousers. And beat up Vans skate shoes were substituted for penny loafers with more frequency than usual. Around this time, the Golf brand also took major strides forward by dabbling in more cut and sew pieces like sweaters, cardigans, and puffers. If Cherry Bomb was Tyler experimenting with a more mature attitude, Flower Boy saw it take the forefront in a way that didn’t feel forced. This era also introduced Tyler’s new footwear partnership with Converse, which resulted in the popular Golf Le Fleur line. The sub-label mostly offered takes on the One Star remixed with a special flower logo on the side panel and unorthodox materials like faux croc skin or quilted velour. Eventually, Tyler would even release his own original silhouette, a chunky low top dubbed the Gianno, in 2019.
Album Released: 2019
Signature Items: Monochromatic suits, white derbys, and a platinum blonde wig
Tyler’s Igor era might be the most easy to define. That’s because the musician decided to go full method actor mode for this album run. When he was on stage performing, in music videos, or doing any sort of album promo, we saw Tyler dress up in bright, monochromatic suits, white Dr Martens 1461s, and a blonde wig that had him looking like Coconut Head from Ned’s Declassified. There were even statues of the Igor character placed in various cities to promote the project. When he wasn’t in character, he was dabbling into the world of luxury fashion. Appearing in 2020’s Gucci Tailoring campaign alongside his buddy ASAP Rocky and punk rock legend Iggy Pop is a prime example, which further illustrated Tyler’s growth throughout his career. Did anyone imagine the kid biking on Fairfax in 2011 would be a star in a global campaign for a major fashion house?
The unorthodox style choice of Igor matched up perfectly with the sound of the album that is Tyler’s most experimental output to date. Considering the accolades that Igor would go on to receive, it won a Grammy for Best Rap Album in 2020, this will easily go down as one of Tyler’s most memorable eras.
Album Released: 2021
Signature Items: Pleated trousers, wool sweaters, penny loafers, and a furry Ushanka hat
Tyler can certainly pull off a Ushanka. The furry Russian cap has been a constant throughout the rollout of Call Me If You Get Lost. The Ushanka isn’t entirely new to Tyler’s wardrobe though. The most obvious instance of him rocking one in the past probably came on the red carpet of the 60th Grammys back in 2018. He paired a white colorway of the winter hat with a baby blue wool Supreme overcoat and matching Louis Vuitton scarf. It was almost a precursor of sorts to the more luxury-leaning vibe we have seen from Tyler in the video snippets that have rolled out over the past few days that included everything from vintage LV monogram trunks overflowing with clothing to vintage sports cars. The wardrobe has remained classy too. Sweater vests layered with white T-shirts, brown trousers, tasseled loafers, it’s all there. Tyler’s day-to-day wardrobe has most closely matched this era ever since.
Album Released: 2024
Signature Items: Mask, “Eisenhower” jacket, aiguillette, and traditional Rwandan Amasunzu hair
Tyler, the Creator’s Chromakopia era is one of his most theatrical to date. He adopted a surrealist persona named St. Chroma who was cloaked in military-inspired tailoring and a flesh-tone face mask.
The “Eisenhower” jacket, or “Ike” jacket is a U.S. military garment first introduced during World War II and named after General Dwight D. Eisenhower. Designed to replace the bulky service coats of the past, the Ike jacket featured streamlined details that were meant to offer both mobility and a polished appearance: cropped length, trim fit, shoulder epaulets, and flap pockets. Tyler’s version of the jacket features custom elements like a gold aiguillette that signals ceremonial rank and an Okonma nameplate that fit into the mid-century feel of Chromakopia‘s visuals.
The rest of the uniform added deeper layers of symbolism. The mask concealed identity and the Amasunzu-inspired hair paid homage to cultural heritage. Traditionally worn by Rwandan warriors, the hairstyle symbolizes strength, status, and virtue.
Album Released: 2025
Signature Items: ‘Glass’ trucker hat, red leather pants, a gold dookie chain, and Cazal shades
Tyler, the Creator’s Don’t Tap the Glass era strips back the theatrics of Chromakopia and trades them for something more playful. In the announcement post for the album on Instagram, Tyler writes, “Made for body movement.” Instead of polished uniformity, Tyler leans into contrast.
The look centers around a trucker hat with “Glass” printed on the front, a reference to the album title and a visual anchor that shows up throughout the rollout. It’s paired with clear Cazal shades, and a monochromatic look that has become Tyler’s signature style formula. The styling signals a revolt against sanitized nightlife and the anxiety of being watched. It also acts as a fitting homage to LL Cool J and the hip-hop style of the ’80s and ’90s. This is the era that Tyler wants to take it back to. It’s a stark contrast from modern times where dance floors have become full of phones and self-consciousness. Don’t Tap the Glass is about letting go and reclaiming the dance floor for its original purpose.
