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Prince -

Prince exuded style everywhere he went. He began pushing the boundaries of what masculinity looked like from his very first record cover, and didn't stop until his dying day.

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Grace Jones -

Grace Jones' androgynous style and strong personality have made her a legendary and otherworldly figure. Jones has been an inspiration to countless people, from fans to colleagues, ever since the turn of the 1980s.

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Jimi Hendrix -

A legendary figure of the 1960s counterculture movement and one of the greatest guitar players to ever live, Jimi Hendrix was also known for his psychedelic blouses and iconic headbands.

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Grimes -

There is no denying that Canadian musician Grimes is one of the most stylish and unique music stars of today.

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Tyler, the Creator -

From his beginnings as an edgy skate rapper to the multi-faceted and fascinating musician he is today, Tyler, the Creator is easily one of the best-dressed figures in music these days.

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Marvin Gaye -

Marvin Gaye, the "Prince of Motown" himself, was never caught looking anything short of spectacular. On this particular day at Radio City Music Hall in 1983, it looks like Gaye decided to take his typical sharp look even further with this glamorous sequined jacket.

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Janelle Monáe -

One of the 21st-century's most consistent icons of music and fashion, Janelle Monáe has challenged social norms throughout her career. Monáe has stated before, "I feel like I have a responsibility to my community and other young girls to help redefine what it looks like to be a woman. I don’t believe in men’s wear or women’s wear, I just like what I like."

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Miles Davis -

Miles Davis had a career as arguably the most important jazz musician in history for more than five decades. During that time, not only did he reinvent music on more than one occasion, but fashion as well. From his irresistibly cool looks of the '60s to the controversial, bug-eye-bespectacled costumes of the 1980s, Davis was never anything but true to his own tastes.

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Björk -

The Icelandic alien queen known as Björk stands in a league all her own. Not only has she stayed on the cutting edge of music for nearly three decades, Björk has also turned the ideas of style and fashion on their heads on multiple occasions.

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Liberace -

One of the most sought-after entertainers in the world during the mid-20th century, Liberace lived, and dressed, by one motto: too much of a good thing is wonderful. His insatiable hunger for natural diamonds and natural fabrics led him to be one of the best-dressed performers of his time.

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David Bowie -

Few rock stars influenced fashion as much as David Bowie. From the out-of-this-world swagger of Ziggy Stardust to the soft and stylishly disheveled Thin White Duke, Bowie stayed on the cutting edge throughout his career.

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Siouxsie Sioux -

It's impossible to overstate Siouxsie Sioux's influence on music and fashion. The Siouxsie and the Banshees front woman's classic makeup look and frantic hairstyles inspired an entire generation of goths and punks, and continues to do so to this day.

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André 3000 -

Arguably the greatest fashion icon of 2000s hip hop, André 3000 challenged preconceptions of what the genre was supposed to look like. From his countless stage looks to his iconic horse jockey outfit from OutKast's 'Hey Ya' music video, he's always oozed cool.

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Diana Ross -

From her start as a member of arguably the most successful soul group of all time, the Supremes, and through her illustrious career as a solo artist, Diana Ross has always dressed her absolute best.

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Leonard Cohen -

As if his smooth and haunting baritone voice wasn't enough, Canadian singer-songwriter Leonard Cohen was usually the most stylish man in the room, without even trying.

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Debbie Harry -

The American darling of new wave, Debbie Harry and her band Blondie were instrumental in the genesis of the musical genre and aesthetic that took a generation by storm.

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Missy Elliott -

A pioneer of late '90s and early 2000s hip hop, Missy Elliott set the standards for street fashion for her time. The 'Supa Dupa Fly' artist truly was, and remains, exactly that.

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Dolly Parton -

America's eternal sweetheart and the "Queen of Country," Dolly Parton's style, although sometimes extravagant, has always been inspired by her humble Appalachian Dixieland beginnings.

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Bob Dylan -

The legendary singer-songwriter's style worked because it was simple, and he let his own natural coolness carry him the rest of the way. Keeping the beatnik style alive, Dylan was known to rock the black turtle neck and the persistent cigarette. And don't forget the harmonica!

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Stevie Wonder -

The prolific pioneer of a wide range of genres, from funk to soul to pop, is just as well known for his iconic braids-and-sunglasses look as he is for his contributions to music.

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Bruce Springsteen -

The hero of the working class, Bruce Springsteen has always dressed the part, with his ripped sleeveless shirts, denim, and his now-iconic red headband.

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Erykah Badu -

The godmother of neo-soul and one of the most fascinating personalities in music, Erykah Badu always had a flair for grandiose, consistently rocking oversized hats and hair wraps with ease and finesse.

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Stevie Nicks -

Stevie Nicks was the witchy and bohemian face and voice of a generation. The Fleetwood Mac singer would never be seen out of her iconic wispy, free-flowing dresses during the band's heyday.

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James Brown -

Mr. Dynamite himself, James Brown was known as the "hardest working man in show business," and was also one of the best dressed. The funk pioneer could never resist a good cape or ruffled cuff.

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Elton John -

One of the most legendary figures in the history of music, Elton John has never shied away from loud and bombastic looks throughout his career, and his fearless fashion choices have always paid off.

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Madonna -

The "Queen of Pop" and easily one of the most successful pop culture figures of all time, Madonna has inspired multiple generations of people around the world with her ever-evolving  kaleidoscopic looks.

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Tom Waits -

A man of who perfected the character of the sentimental drunkard, and later the musical madman, Tom Waits' blithe personality was amplified in his early days with casual yet timeless looks, always disheveled but smart.

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Chet Baker -

Known for his hauntingly beautiful trumpeting and his angelically androgynous crooning, Chet Baker was always dressed in sleek, simple suits that defined the jazz styles of his day.

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Elvis Costello -

Elvis Costello has always walked the fine and stylish line between sleek and street smart. 

Sources: (GQ) (Flavorwire) (Glamour)

See also: Memorable fashion moments from the '90s

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