The Early Days: Luxury Streetwear Pioneer
Back in 2011, when ASAP Rocky first hit the scene with Peso, it was clear he wasn’t your average rapper. While hip-hop was still dominated by oversized tees and Jordans, Rocky was rapping about Raf Simons, Rick Owens, and Maison Margiela. His aesthetic? A perfect blend of Harlem streetwear and European luxury, setting him apart from the rest of the game. His bold fashion choices made him an instant standout, elevating his status beyond music and into the realm of high fashion tastemakers.
His influence skyrocketed when he dropped the line: "Raf Simons, Rick Owens, usually what I'm dressed in." Suddenly, these designers—once reserved for fashion insiders—were on the radars of hip-hop heads worldwide. Rocky helped bridge the gap between streetwear and high fashion, making designer labels feel accessible to a new generation of style enthusiasts. His early love for bold prints, high-end sneakers, and monochromatic fits laid the foundation for the style evolution that followed.
How Pretty Flacko Became One of Fashion’s Most Powerful Voices
ASAP Rocky isn’t just a rapper—he’s a walking fashion movement. From his early days blending high fashion with streetwear to becoming the Creative Director of Ray-Ban, his influence has been undeniable. While many artists flirt with fashion, Rocky has fully embedded himself into the culture, shaping trends and redefining hip-hop’s relationship with style.
Now, as he takes the reins at Ray-Ban, it’s time to examine the evolution of his fashion empire and why this move makes perfect sense. His ability to seamlessly mix underground style with luxury brands has made him one of the most influential figures in both music and fashion.
March 5th. Written By Ryan Packer
The Fashion Takeover: Cozy, High Fashion, and Risk-Taking
From 2015 to 2018, Rocky transitioned from a streetwear star to a fashion powerhouse. He co-signed VLONE, ASAP Mob’s own fashion brand, which became a streetwear staple. But while his peers leaned heavily into hood aesthetics, Rocky expanded his vision. He rocked head-to-toe Dior, becoming one of the first rappers to be fully embraced by the luxury house. He also pushed the "Cozy Boy" aesthetic, mixing oversized silhouettes, luxury knitwear, and effortless layering.
Rocky’s fearless approach to fashion challenged traditional norms in hip-hop. He redefined masculinity in hip-hop fashion, donning pearl necklaces, skirts, and the now-iconic Gucci babushka headscarf. By this point, Rocky wasn’t just wearing designer—he was setting trends that designers were now following. His ability to effortlessly mix streetwear with avant-garde high fashion solidified his status as a true style innovator.
Modern-Day Flacko: The High Fashion Blueprint
Today, ASAP Rocky has refined his style into something more curated—a mix of clean-cut tailoring, vintage influences, and high-fashion experimentation. He’s no longer just wearing the hottest brands; he’s curating an aesthetic that feels uniquely his. Whether it’s sporting archival Prada, experimenting with gender-fluid pieces, or effortlessly layering textures, Rocky’s style is as calculated as it is influential.
One of the biggest shifts? His relationship with Rihanna. As half of fashion’s most powerful couple, Rocky’s looks have evolved to complement her bold yet elegant style. They’ve turned red carpets into fashion moments, from his quilted Met Gala fit to their effortless, coordinated streetwear. Together, they continue to push boundaries, influencing both casual and high-end fashion trends worldwide.
ASAP Rocky x Ray-Ban: The Perfect Match
In early 2024, ASAP Rocky was announced as the Creative Director of Ray-Ban, a move that caught many off guard but actually makes total sense. Rocky has always been an eyewear icon. Whether it’s oversized 90s-style frames or vintage aviators, his sunglass game is undefeated. His ability to set trends in eyewear made him the perfect candidate to inject fresh energy into the brand.
Ray-Ban, a legacy brand, has played it safe in recent years, relying on its classic designs. Rocky’s appointment signals a shift toward a more fashion-forward, culturally aware approach. Instead of just being a face for the brand, he’s actively involved in design. His upcoming Ray-Ban collections will likely merge classic silhouettes with experimental, trendsetting details. This isn’t just another celebrity collab—it’s a real creative leadership role, marking yet another step in Rocky’s transformation from fashion icon to industry executive.
The Legacy: What’s Next for Flacko?
ASAP Rocky has proven time and time again that his fashion influence goes beyond hype. Whether he’s making oversized pearl necklaces a must-have, pushing gender-fluid styling in hip-hop, or redefining the role of a rapper in luxury fashion, his impact is undeniable. He has successfully navigated between music, fashion, and brand collaborations, solidifying his place as one of the culture’s most influential figures.
With Ray-Ban under his creative direction, we can expect even more of his impeccable taste to shape the industry. Could this be the start of Rocky launching his own fashion house? One thing’s for sure: Pretty Flacko isn’t done changing the game. As he continues to elevate his influence, it’s clear that ASAP Rocky’s imprint on fashion will be felt for years to come.
