5 of The Best Dressed Rappers of All Time

Some rappers rap.
Some rappers dress.
And then there are the chosen few who walk out the house like the final boss of Fashion Week for absolutely no reason.

Let’s talk about the ones who made the rest of us question our closets on a random Tuesday morning.

Photo of A$AP Rocky wearing a high-fashion streetwear outfit, showcasing his signature cutting-edge style. — A$AP Rocky proving once again that he wakes up dressed better than the rest of us on our birthday.

1.A$AP Rocky

Rocky dresses like a man who wakes up, picks up a random garment shaped like a science experiment, shrugs, and somehow makes it a trend. Everybody else is trying; he’s just vibing. He can slip on an $8,000 coat shaped like a lampshade and people be like “Wow. Art.”

Photo of Kanye West wearing long sleeve polo layers the beginning of college dropout — Kanye West before in his signature “I look simple but this outfit cost mortgage money” mode.

2. Kanye West

Ye will step out in three neutral layers, a boot that looks like it survived the apocalypse, and a shirt that’s basically a rectangle—and the entire fashion world collapses like, “Genius. Innovator. Visionary.”

Say what you want about Ye, but the man could wear a beige trash bag and somehow sell it for $450. Gotta Love Ye…

Image of The Notorious B.I.G. wearing a colorful Coogi sweater and sunglasses, showcasing his classic 90s luxury style. — The Notorious B.I.G. looking like your rich uncle who only wears designer and gives terrible financial advice.

3. The Notorious B.I.G

Biggie dressed like your rich uncle who only shows up twice a year but somehow owns every Versace item ever created. The Coogi sweaters alone? Legendary. The man pulled up looking like comfort, luxury, confidence, and a tax bracket we all aspire to.

Image of Pharrell Williams wearing a bold, futuristic outfit with accessories like pearls and a wide-brim hat. — Pharrell Williams looking like he time-traveled from the future just to flex on us.

4. Pharrell Williams

Pharrell has been dressing like the future since the past. He can wear pearls, shorts, a giant hat the size of a satellite dish, and still look cooler than your entire friend group combined. He’s the reason half the trends today exist. The man sneezes and fashion shifts.

Photo of Slick Rick wearing oversized gold chains, pink shirt, and his signature eyepatch. — Slick Rick pulling up dressed like hip hop royalty every day of his life.

5. Slick Rick

Slick Rick didn’t “dress”—he performed. Chains? Heavy. Furs? Dramatic. Eyepatch? Iconic. He looked like he robbed a royal palace but did it politely. No one has ever committed to “main character energy” like The Ruler. He walked so your favorite flashy rapper could sprint.

The Real Talk

These five didn’t just put on outfits—they created entire eras. They shaped hip hop fashion, luxury streetwear, and every “inspo” board on Pinterest someone’s using right now.

And let’s be honest… the rest of us are still trying to catch up or we just don’t get it. GQ’s deep dive into hip hop style evolution