The Freshest: 23 most fashionable rappers of all time

Once seen as mere self-expression, fashion has become a very important tool in Hip Hop's toolbox. It is one of the ways the genre has propelled itself to the forefront of culture. Along with the ever-changing terminology — such as jiggy, getting fly, fresh to death, or drip — rappers choosing what to wear has always been about being original and oftentimes, being first. Beyond visually declaring who they are, it has also been a technique to influence the masses. From industry vets like Lil’ Kim to newer faces like Kendrick Lamar and ASAP Rocky, take a look at some of the most fashionable rappers of all time below – in no particular order.

Known for his eye patch, gargantuan jewelry and platform kicks, Slick Rick is a walking manifesto of personal style, leaving his colorful and undeniable mark wherever he goes. His unmistakable flair has caused clothing brands like Supreme to license his image and has even inspired countless Halloween costumes. Slick’s jewelry collection continues to be an inspiration and is even expected to be on display in an exhibit at the American Museum of Natural History in New York City this May.

The Kings from Queens cemented their trailblazing style with Kangol hats, tracksuits, oversized Cazal sunglasses and slick attitudes to match their boisterous raps. However, it was their love of a certain Adidas Superstar model that forever immortalized them in the history books. From a rap song titled "My Adidas" to a partnership with the brand that spanned decades, a new mutually beneficial formula was born between Hip Hop and fashion. For that, we will always salute Run-DMC.

Kool Moe Dee, hailing from New York City, rose to rap prominence as a part of the Treacherous Three rap group before going solo. At that point, he established a unique look of custom leather jackets and beret hats in a variety of colors. He would often top the outfits off with Porsche sunglasses and major gold jewelry, which set the standard for MCs like Rakim and ASAP Rocky.

There are so many styles and clothing brands that rose to prominence due to Wu-Tang Clan, the rap supergroup from Staten Island, New York. Brands like Polo Ralph Lauren and Clarks Originals immediately come to mind because of Raekwon and Ghostface. Plus, their love of audacious jewelry still reigns and inspires generations to come.

"However, livin' better now, Coogi sweater now,” The Notorious B.I.G. spit on his hit "Big Poppa." The Brooklyn native didn’t just rap it — he lived it. Though his career was cut short, B.I.G. managed to cement himself as one of the smoothest, best-dressed stars in no time thanks to his suave style of Coogi sweaters, Versace sunglasses and even BAPE long before the masses caught on. We’ll always love Biggie!

2Pac had an approach to rap and fashion that was all his own. As much of a man of the people as he was mysterious and unpredictable, the East Harlem native bounced between high-end and everyday workwear looks with ease. Whether he was wearing unique and luxurious leather sets or Karl Kani denim, 2Pac owned every look. He was also known for his accessories, sporting numerous tied beanie hats and popularizing the gold rope chain. His most iconic looks are still being copied and reimagined by rappers today.

Sean “Diddy” Combs himself set the tone for glamour in Hip Hop. Initially bursting on the scene wearing classic sportswear looks, Diddy evolved the landscape through his style and the start of clothing brand Sean John. By mixing fashion and entertainment in an unprecedented way, he took Hip Hop to stylish new heights and revolutionized the trajectory of rappers’ clothing lines.

Nas, the God MC from Queens, rose to prominence alongside his peers in the ’90s, which most consider the golden era of fashion. Although more subdued in style than others, Nas quickly established unique looks for himself throughout his different eras, including oversized leather, cowboy hats and luxurious furs. As time went on, he elevated his look to a style-equivalent of a Hip Hop James Bond without missing a step or his beloved Mets hat. Nas is a classic example of aging with chic grace.

OutKast, comprised of André 3000 and Big Boi, helped set the tone for Southern Hip Hop and flaunted unique looks to match. Whether it was through costume-like direction from André 3000 or classic country gentleman styles from Big Boi, their genre-defying looks changed with the mood of their music. Even through solo projects, the duo continued to create distinctive personas and ensembles to match, which inspired the generations after them.

Lil’ Kim, the diminutive rapper from Brooklyn, arguably set the image for what the modern female rapper looks like. Through her boisterous and provocative rap style, she commanded her sex appeal and formidably harnessed fashion that continues to set the bar for personal expression. From her love of all things logo and high-end to her ever-changing hairstyles and colors, Lil’ Kim wore it all and inspired designers behind some of the biggest brands, including Alexander McQueen and Marc Jacobs. Celebrities’ constant referencing of her iconic looks also cemented her impact as one of the most fashionable lyricists of all time.

The “dark-skinned, Christian Dior poster girl” was a fashion giant in her own right. Through her raw, raunchy and unapologetically Trinidadian rap style, Foxy Brown commanded the scene. She mixed modernity and edgy designers like Calvin Klein and Christian Dior as effortlessly as she wore Sean John velour suits. The native New Yorker was also a pioneer in the way that she name-dropped almost every relevant brand in her bars during her tenure as one of the greatest female MCs of all time.

Missy “Misdemeanor” Elliott stole the spotlight through her fluid music style and unique looks. Whether it was through her gravity-defying black plastic bag suit or her notorious collection of tracksuits, Elliott forged several looks that are still a topic today. She also collaborated with brands like Adidas, Gap and MAC Cosmetics, helping to diversify and open lanes for self-expression not seen before.

No list would be complete without Busta Rhymes, the Brooklyn-born rapper who debuted in the mid-’90s with a larger-than-life persona and looks to match his quick bars. The lyrical giant could often be spotted in custom looks that took on a life of their own. To stand out, he mixed leather, bold prints, hats and jewelry. His influence looms large on modern rappers, like Offset, who all take a page out of his book.

Lil Wayne has lived many lives and has the outfits to match. From his early Hot Boys days, which consisted of mostly oversized white T-shirts and denim, to his iconic and most memorable BAPE era in the mid-2000s, Weezy F. Baby has worn it all with an unbothered aura. Even to this day, the trailblazer continues to sport unique looks from controversial brands like MSCHF and more without missing a step.

Harlem's very own Cam’ron hit the scene with a charismatic persona to match his braggadocious raps. Furs, Jeff Hamilton jackets, large diamond earrings and pinky rings all come to mind regarding his trademark style. He solidified his spot among the Mount Rushmore of fashionable celebrities the fateful day he decided to wear a pink fur jacket with pink accessories — including a Baby Phat cellphone and matching Range Rover. That boldness is what separated him from the pack, and it continues to inspire many of his fans to this day.

Pharrell Williams is one of the leading arbiters of fashion in Hip Hop, and there isn’t a style the icon hasn’t made his own during his lengthy career. From his beginning days as part of The Neptunes — wearing skate-inspired looks — to his more boisterous solo career era during which he donned BAPE and diamonds by Jacob the Jeweler, Williams has always been an early adopter and pioneer. Now as the men's creative director of Louis Vuitton, there’s no shortage of trailblazing looks from the Virginia native.

Kanye West's impact on fashion knows no bounds. Since his debut as a producer and rapper on Roc-A-Fella Records, he’s always stood out. Flaunting pink Polos and sweaters — a more preppy style compared to the avant-garde fashion he's known for now — Ye has always been at the forefront and ahead. His countless collaborations and clothing lines with brands like Nike, Adidas, Gap, A.P.C. and beyond easily cemented him as an artist with a huge influence on the industry.

Eve, the Philadelphia-born, self-proclaimed “pit bull in a skirt,” was also a beloved fashion maven. During her heyday, she favored looks that complemented her legendary paw print tattoos and sported every brand from Christian Dior to Chanel — all while maintaining a blooming professional acting career that included her own TV show and talk show. She also moonlighted as a designer with her clothing line Fetish by Eve, which was a success for many years.

Kid Cudi's versatility in fashion is indisputable. Since his debut in 2009, the multitalented artist has been known for streetwear and Japanese brand-influenced looks. He’s been at the forefront of fashion ever since collaborating with brands like BAPE, Giuseppe Zanotti, Louis Vuitton and Off-White, all while maintaining a steady musical output. As an avid sneaker and art collector, Cudi is in the top percentage of fashionable celebrities and even has his own brand, Members of the Rage, inspired by ’90s grunge and the soul of Hip Hop.

ASAP Rocky is the perfect combination of all the best-dressed rappers before him. He has the charisma and class of old school Hip Hop mixed with the edge and spark of high fashion. From the beginning, the former ASAP Mob member has made it known how important style is to his persona. He proclaimed himself the “jiggy n**ga with the gold links,” and brands took notice. Back in 2016, the Harlem native became the first person of color to serve as the face of Dior Homme and followed up by fronting campaigns like Gucci, Guess Originals, Marine Serre and Raf Simons.

When Kendrick Lamar said, “I’m best-dressed moving forward" on “The Hillbillies,” he wasn’t lying. He's since supported that statement with a Chanel collaboration through his powerhouse marketing agency, pgLang; a sneaker collab with Converse ,and constantly wearing innovative Black designers like Martine Rose and Wales Bonner. Lamar has come a long way from the laid-back style of his West Coast upbringing, which consisted mostly of hoodies and classic footwear like the Nike Cortez.

Tyler, The Creator knows no bounds, musically or fashion-wise. He launched his GOLF WANG brand and collaborated with companies like Lacoste and Louis Vuitton. Early in his career, the multihyphenate was known for his love of Supreme, which elevated its taste to unique, tailored garments and profound color usage. Tyler has also become a beauty magnate, launching fragrances and nail polish through his line GOLF le FLEUR*.

Despite not being a typical fashionable rapper in the designer-heavy sense, Nipsey Hussle understood the importance of style and established his brand, The Marathon Clothing, early in his career. Working closely with his stylist, Groovey Lew, Hussle was able to come up with a uniform of looks all his own. He created logo-less custom sweatsuits for each of his performances and promotional looks that would posthumously set the tone for many collections with Puma. By preaching ownership and showcasing continuous brand identity, he was able to cultivate a timeless persona.

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