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.

Video will return here when scrolled back into view
Angela Bassett Reveals the Mission: Impossible Birthday Surprise That Got Tom Cruise Dancing

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.

Straight From The Root

Sign up for our free daily newsletter.

Latest from The Root

Black-Owned Interior Design Brands That'll Give Your Home a Glow-Up in 2026

Black-Owned Interior Design Brands That’ll Give Your Home a Glow-Up in 2026

If you’re looking to bring some new style into your personal space in 2026, we’ve rounded up some of our favorite Black furniture and home decor brands to help …
Don Bryant and Other Black Celebs We Lost In 2025

Don Bryant and Other Black Celebs We Lost In 2025

We are recognizing the Black celebs who left us in 2025 …
Why the Democratic Party Is Setting Itself Up For Failure Ahead of Midterm Elections

Why the Democratic Party Is Setting Itself Up For Failure Ahead of Midterm Elections

As we prepare for the 2026 midterms, the Democratic party could be its own worst enemy …
5 Most Shocking Parts of Marjorie Taylor Greene's Bombshell New York Times Interview

5 Most Shocking Parts of Marjorie Taylor Greene’s Bombshell New York Times Interview

The firebrand Republican representative sat with The New York Times for a candid interview that will have more than a few eyebrows raised …
Tyler Perry Brings Receipts, Calls Sexual Assault Lawsuit a '$77 Million Money Grab Scam'

Tyler Perry Brings Receipts, Calls Sexual Assault Lawsuit a ‘$77 Million Money Grab Scam’

In June 2025, Tyler Perry was sued by an actor for sexual assault. Now, yet another man is making similar allegations–but Perry is pushing back! …
Video of Boxing Champ Anthony Joshua in Fatal Car Crash Leaks

Video of Boxing Champ Anthony Joshua in Fatal Car Crash Leaks

Ten days after beating YouTuber Jake Paul in a boxing match, Anthony Joshua was reportedly driving in a vehicle when it crashed into another …
Why Black Folks Need to Follow Kwanzaa's Wealth-Building Principle of Ujamaa Now More Than Ever

Why Black Folks Need to Follow Kwanzaa’s Wealth-Building Principle of Ujamaa Now More Than Ever

The fourth day of Kwanzaa is all about the principle of cooperative economics. Here are ways you can build and maintain wealth in your community …
Black Internet Responds to Petition to Deport Nicki Minaj From the U.S.

Black Internet Responds to Petition to Deport Nicki Minaj From the U.S.

Rapper Nicki Minaj has been a trending topic a lot as of late. But unfortunately for her, it’s now causing some people to take some truly dramatic measures! …
Behind Beyoncé's New Billionaire Status

Behind Beyoncé’s New Billionaire Status

Beyoncé is now officially rich-rich! But how has she amassed so much money? Let’s break it down by the numbers! …
N.Y. Man Stabbed to Death on Christmas While Covering a CVS Shift He Was Never Scheduled to Work

N.Y. Man Stabbed to Death on Christmas While Covering a CVS Shift He Was Never Scheduled to Work

23-year-old Edeedson Cine, of Long Island, covered a co-worker’s CVS shift on Christmas Day at the last minute. But he never made it home …
The Reason Black Churches Use Watch Night Services to Ring in the New Year is Deeper Than You Think

The Reason Black Churches Use Watch Night Services to Ring in the New Year is Deeper Than You Think

We’re looking at the history of watch night, a New Year’s Eve tradition for Black Americans that goes back to the Civil War …
Before You Step Into 2026, Do You Understand Your Assignment? Here's Some Help.

Before You Step Into 2026, Do You Understand Your Assignment? Here’s Some Help.

Before the ball drops on 2026, you still have time to figure out your assignment for the new year …
All You Need to Know About Diddy's Sons' Docuseries Trailer

All You Need to Know About Diddy’s Sons’ Docuseries Trailer

Diddy’s sons’ docuseries trailer dropped last night on Twitter, and folks are not holding back on their initial thoughts …
Black Man Who Saved Baby From Viral Pit Bull Attack in NYC Speaks out

Black Man Who Saved Baby From Viral Pit Bull Attack in NYC Speaks out

Bodybuilder Kevin Richardson is being called a hero after saving a one-year-old from a vicious Pit Bull attack in NYC …
New Details Emerge After 'Lion King' Broadway Star Found Fatally Stabbed Days Before Christmas

New Details Emerge After ‘Lion King’ Broadway Star Found Fatally Stabbed Days Before Christmas

Broadway alum Imani Dia Smith, who played Young Nala in “The Lion King,” was found slain just days before Christmas. Now, a suspect is in custody …
How Trump's Power is Crumbling and The Resistance is Growing

How Trump’s Power is Crumbling and The Resistance is Growing

With a 36% approval. High-profile defections. A surging opposition. The cracks in President Trump’s armor aren’t just showing, they’re widening …
Nicki Minaj's MAGA Support Shouldn't Surprise You: Her True Colors Have Been Visible for Years

Nicki Minaj’s MAGA Support Shouldn’t Surprise You: Her True Colors Have Been Visible for Years

Nicki Minaj’s recent MAGA alignment has some Black folks shocked and calling her crazy for the sudden move, but her behavior over the years has consistently foreshadowed her political leanings …
What's Black at Sundance 2026: Movies, Documentaries and More!

What’s Black at Sundance 2026: Movies, Documentaries and More!

Sundance Film Festival is back again and that means, so is our list of Black-leading or centric films you might want to keep an eye out for in 2026! …
Trump's Christmas Day Airstrikes in Nigeria Spark Outrage and Divide

Trump’s Christmas Day Airstrikes in Nigeria Spark Outrage and Divide

On Christmas Day, the Trump Administration confirmed “powerful and deadly” U.S. military strikes against ISIS-linked militants in northwest Nigeria …
These 7 Black Female Senate Candidates Could Rewrite History in 2026

These 7 Black Female Senate Candidates Could Rewrite History in 2026

From Texas to South Carolina, a new wave of Black women candidates is stepping into the U.S. Senate race, potentially making history in the 2026 election cycle …