6 Of The Best Dressed Male Rappers
We're giving these hip-hop heavyweights their flowers for always PTSO
Album covers (from top left to bottom right): Stankonia by OutKast, JEFFERY by Young Thug, LIVE.LOVE.A$AP by A$AP Rocky, Igor by Tyler, The Creator.
When you’re a superstar, all eyes are on you—and the clothes you wear. Rappers, in particular, often serve as the blueprint for the streetwear subculture, and over the years, plenty of them have left their mark on fashion, for better or worse (we still can’t forgive Pooh Shiesty for making ski masks popular). Thankfully, some have pushed the boundaries of style and cemented their place as true fashion trendsetters. Let’s look at the rappers who wear the crown as the kings of hip-hop style.
6 Best Dressed Male Rappers:
Tyler, The Creator
What makes a true trendsetter? Is it rocking the latest fad or debuting the newest looks straight off the runway?
For Tyler, The Creator, it seems that confidence is the only ingredient you need.
As a true sartorial chameleon, Tyler reinvents his aesthetic with each album era. We've seen him embrace the quirky skater look—heavily donning graphic tees and Vans—during his Odd Future days, and evolve to sophisticated, militant styles in his current Chromakopia run.
Even his casual, everyday outfits stand out, often leaning preppy and paired with a pastel color palette.
It’s not just us who recognize his style influence either. His eye for fashion landed him a Louis Vuitton collab, and let's not forget his own labels, Golf le Fleur and Golf Wang.
Tyler may be a style shapeshifter, but one thing remains consistent: his confidence. Unconcerned with following trends, he stands in a lane of his own, (name another rapper who had fans dressing up in a blonde bob for Halloween?), fueling anticipation for what he’ll wear (and maybe design) next.
2. OutKast
OutKast were the OG hip-hop trendsetters with their experimental sound—and their style was no different. With an eclectic mix of traditional streetwear and an old-school Southern gentleman aesthetic, André 3000 and Big Boi paved the way for later hip-hop trends.
During their 2003 Speakerboxxx/The Love Below era, their stylistic duality really shined through. André 3000 was more playful and whimsical with his fits, while Big Boi embraced a sporty, comfy vibe. While their styles represented two ends of the spectrum, they complemented each other perfectly, inspiring fans to find their distinct swag.
Continuing their generational run was their 2006 film Idlewild. Here, OutKast kickstarted the vintage American trend that dominated the 2010s. (Remember when all the rappers rocked suit jackets with denim jeans and fedoras?)
These two were way ahead of their time, and to this day, still throwin’ fits.
3. A$AP Rocky
A$AP Rocky, the self-proclaimed “pretty MF” (and Rihanna’s baby daddy), is a fashion killa, (no pun intended), who regularly breaks traditional fashion rules.
Hailing from Harlem, New York, Rocky serves unforgettable looks on the daily. Whether he's rocking oversized suits, sheer blouses, or a crossbody bag, you just know he’s going to add his own swagger.
His self-described “ghetto expressionism” earned him a spot as a muse for luxury fashion houses like Bottega Veneta and Gucci. In 2024, he even took home the Cultural Innovator award at the Fashion Awards (finally, fashion is giving him the credit he deserves!).
Rocky is known for wearing unconventional accessories and vintage pieces that stand out, yet somehow, he makes them look flawless. And of course, he always rocks his signature braids and pearl hair clips. Say what you want about his style, but Rocky is an icon (and probably your favorite rapper's OOTD inspo).
4. Busta Rhymes
If Afro-futurism had a spokesperson, Busta Rhymes would be front and center. When he first popped out in the ‘90s, he set himself apart from hardcore rappers by adopting flamboyant styles—we're talking metallic bodysuits, leopard-print jumpsuits, and leather ensembles, just to name a few.
While rappers during his time were wearing baggy jerseys and backwards jeans, Busta Rhymes took a larger-than-life approach to fashion, which fit perfectly with his animated flows and disorienting visuals. Just watch his 1998 “What’s It Gonna Be?!” video with Janet Jackson and you’ll see what we mean.
5. Young Thug
Everybody say Slatt, keep it going!
When we think about the traditional street rapper's aesthetic, skinny jeans, Jordans, and white tees may come to mind. But for Young Thug, subverting gender norms has always been his distinctiveness.
We've seen rappers rock the androgynous look, but none have ever been as influential as Thugger. Nowadays, you've got inner-city kids wearing skirts and painting their nails—none of which could have been done without King Slime doing it first.
No deep dive into Thug's style would be complete without mentioning his 2016 JEFFERY mixtape cover. He wore an Alessandro Trincone dress—a statement so bold, no matter if you hated it or loved it, you couldn't help but respect it.
“In my world, you could be a gangsta with a dress, or you could be a gangsta with baggy pants,” he said in an interview with journalist Sowmya Krishnamurthy. “I feel like there’s no such thing as gender.”
In 2019, he expanded his fashion influence by founding SP5DER, a lifestyle brand inspired by Atlanta culture. Featuring a signature spider-web motif, SP5DER offers hoodies, denim, beanies, sunglasses, and more.
Young Thug’s style is nothing short of avant-garde, and he doesn’t give a fuck who has something to say about his clothing choices. He’s not afraid to wear neon colors, trench coats, wild animal prints, furs, and of course dresses.
Because of his authenticity and fearlessness, we gotta give him his tens!
6. Snoop Dogg
Snoop Dog Performing at the 2011 Maquinaria Festival. Photo by Rodrigo Ferrari
Snoop Dogg doesn’t get a lot of recognition when it comes to fashion, but he should because he effortlessly stays fly.
In the ‘90s, Snoop repped the West Coast by wearing Chuck Taylors, flannel button-ups, and khakis paired with an afro or braids. But by the early 2000s, he embraced ‘70s pimp culture, rocking colorful suits, long fur coats, canes, and top hats. Fast forward to now, he wears more athleisure clothing, fully solidifying his laid-back, “unc” persona.
If y'all haven't regarded Snoop Dogg as a style legend, you definitely should now. Plus, who else do you know that can rock a silk press and make it look hard AF?
Made it this far? Gone head join the fam on Instagram!