NYFW: These Outfits Prove A$AP Rocky Is the Most Stylish Man in Hip-Hop

The New York MC has been ahead of his time when it comes to his style.

He doesn’t call himself Pretty Flacko for nothing. For years A$AP Rocky has crowned himself as the best dressed in hip-hop, and he has put together the perfect fits to back it up.

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Here’s 100 years of the Best Black Dandyism Heading Into Met Gala 2025

Everything from streetwear to luxury, the Harlem MC can make almost anything look good. Let’s revisit some of his fits over the years that prove why he’s so revered, respected, and influential in the fashion industry.

Paris, 2024

Photo: Getty Images Peter White

In previous years, Rocky would’ve worn another brand’s clothing. But during his AWGE fashion, the rapper opted to go for pieces he created on his own.

New York, 2023

Photo: Getty Images Jackson Lee/GC Images

Everything has been baggy in fashion for the last year and a half, especially in streetwear. But A$AP was able to pull off the baggy clothes with a more casual look.

Met Gala, 2023

Photo: Getty Images Mike Coppola

One of the best things about Rocky is that he doesn’t care what anyone thinks. So he’ll wear a red skirt with confidence and know he’s pulling it off. Gotta respect it.

New York, 2022

Photo: Getty Images Rachpoot/Bauer-Griffin/GC Images

Although he often opts to wear something unique, Rocky can also pull off the lean, classic cut.

Los Angeles, 2022

Photo: Getty Images Jerritt Clark/Getty Images for Amazon Music

Sometimes wearing an otherwise simple outfit with one standout piece is enough to get the job done.

New York, 2021

Photo: Getty Images Raymond Hall/GC Images

Another thing that makes A$AP so fly is that he seems to pull off great fits when he doesn’t even seem to be trying hard.

The Fashion Awards, 2019

Photo: Getty Images Tim Whitby/BFC

An example of Rocky being ahead of his time? In 2019, the baggy look hadn’t quite reached popular culture and he was already pulling it off. This look in particular was designed by Rihanna.

Pre-Grammy Gala, 2019

Photo: Getty Images Steve Granitz/WireImage

This look is a nice switch-up. He’s wearing a 70s styled-suit untucked. It may look crazy to some, but it just speaks to his ability to be unique.

Paris, 2018

Photo: Getty Images Francois Durand/Getty Images for Dior

Some say may say sneakers with dress pants don’t work, but A$AP pulls it off with this Dior look back in 2018.

Paris, 2017

Photo: Getty Images Francois Durand

All-over print can be hit-and-miss for most people. It can be a distraction, but Rocky turned it into a clean look for this Dior fashion show.

Milan, 2017

Photo: Getty Images Robino Salvatore

Again, A$AP just has a knack for pulling off the simple outfits.The 1985 Metallic Jordan 1s are what set this fit off.

Grammys, 2016

Photo: Getty Images Jeff Vespa/WireImage

While most people’s eyes may immediately go toward the Gucci Cardigan he’s wearing, the Gucci jeans are the star of this outfit.

New York, 2015

Photo: Getty Images Ilya S. Savenok/Getty Images for 2015 Tribeca Film Festival

There was a period of time when A$AP was dressing like a 90s rockstar with tucked-in shirts and Black bomber jackets. It added a new layer to his normal streetwear fits.

American Music Awards, 2014

Photo: Getty Images Kevin Winter

Here A$AP is just being A$AP. We know he can’t just wear a regular suit. He has to add something that most people normally wouldn’t wear, like this huge scarf.

Made in America, 2013

Photo: Getty Images Mychal Watts

This outfit was the envy of every hypebeast in 2013. A box logo Supreme tee with a clean Stüssy jacket was as dope as it got nearly a decade ago.

New York, 2012

Photo: Getty Images Johnny Nunez

I know this picture isn’t showing off the full fit. But it’s meant to highlight the hoodie. Pyrex was the brand the late Virgil Abloh founded before creating the now-popular Off-White. Even then, Rocky was bought in on the Abloh hype before it reached the levels it eventually did.

New York, 2012

Photo: Getty Images Taylor Hill

It may be hard to understand now, but this was peak streetwear fashion in 2012. Bred Jordan 1s, skinny jeans, and a letterman jacket. It was all you needed back then.

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