The Ten Most Stylish Musicians Of All Time

For years the fashion houses of Saint Laurent, Ami, Gucci, Burberry, Dior, and in modern times Tom Ford have pushed the envelope of fashion in ways that will last a lifetime. This can also be said for the musicians that wear these brands, after all, fashion, and music go hand and hand and have done so for centuries. From the days of Mozart to the present day, musicians have always helped push the conventions of style, and the great ones create a style all their own. We comprised our list of the top ten most stylish musicians of all time, all were chosen based on their personal style, and influence on the fashion of pop culture as well as the fashion industry.

10. Johnny Cash

The original man in black, Johnny Cash, was born J. R. Cash in Kingsland, Arkansas, and was the fourth of seven children. Although he is primarily remembered as a country icon, Cash’s deep, distinctive bass-baritone voice, for the “boom-chicka-boom” sound of his Tennessee Three backing band; rebelliousness, coupled with an increasingly somber and humble demeanor. Decades before punk rock Cash was the first to dawn the all black everything look, which earned him the nickname “The Man in Black”. He traditionally began his concerts with the phrase “Hello, I’m Johnny Cash.”, followed by his standard “Folsom Prison Blues”.

9. Elvis Presley

Born Elvis Aaron Presley on January 8, 1935, in Tupelo, Mississippi. It is here where he would travel to black southern Baptist churches, and listen to the blues that would help him create the sound that would become Rock & Roll. Presley and his family moved to Memphis, Tennessee, when he was 13 years old. His music career began there in 1954 when he started to work with Sam Phillips, the owner of Sun Records. Though he will always be remembered Elvis’ style deserves way more credit than it’s given. Whatever he wore, be it a tailor-made suit, or a relaxed chunky knit, this singing legend always looked the part.

8. The Beatles

The Beatles were an English rock band that formed in Liverpool, in 1960, with John Lennon, Paul McCartney, George Harrison, and Ringo Starr. They were the original band that started the British rock invasion, they became widely regarded as one of the greatest, and most influential acts of the 1960s. They came to America in the early 1960s with their tailored Moded suits, and all the flare that Swinging London has to offer,, their enormous popularity first emerged as “Beatlemania”, but as their songwriting grew in sophistication they came to be perceived as an embodiment of the ideals shared by the era’s sociocultural revolutions. Threw out the years The Beatles continued to be pioneers in both music, and fashion.

7. Sammy Davis Jr.

Sammy Davis Jr. singer, dancer, Rat Pack member, and all-around entertainer extraordinaire. He broke the boundaries in a time when it was illegal to do so and was one of the greatest talents that existed during the 1950s and ’60s. Though he was the third of the ever-stylish Rat Pack along with fellow members Dean Martin and Frank Sinatra, Davis had a style all his own that set him apart from the rest of the trio. As the landscape of America was going through social changes, Davis never let his race be the center of attention, instead, he let his style, charms, and talents speak for themselves. So much in fact that in September 1967 he became the African-American to grace the cover of GQ. At the height of the civil rights movement, and with the support of Dean Martin and Frank Sinatra, he refused to work at segregated venues, which ultimately led to the integration of nightclub hotspots like Las Vegas and Miami Beach. Throwout the decades to follow he continued to have the style that kept, and talent that kept him relevant.

6. Frank Sinatra

The chairman of the board, Frank Sinatra, had a sense of style from an early age, and Sinatra found success as a solo artist from the early to mid-1940s after being signed by Columbia Records in 1943. With his felt fedoras and tailored suits, Sinatra took the music scene but storm and swooned women for decades. He favored tailor-made suits, and tuxedos over jeans, or slacks. Almost the definition of refinement and class, the singing star had plenty of advice to offer when it came to fashion. According to Ol’ Blue Eyes, one-half inch of a man’s shirt cuffs should protrude from his jacket sleeve, trousers should fall slightly above the shoe, black is the only appropriate color to wear after dark, vests are better than cummerbunds, and you shouldn’t forget to shine your shoes. (All of which are staples here at TheLifeStyleElite.com, and have been featured for years in our popular “Style Wednesday.”) Other great style advice included gold cuff links, perfectly folded pocket scarves, fedoras, conservative silk ties, bow ties, and a distinct lack of jewelry.

5. Miles Davis

Miles Davis; jazz musician, trumpeter, bandleader, composer,  and style icon. Widely considered one of the most influential musicians of the 20th century, and one of the greatest in the Jazz field he has crossed over to a household name. The King Of Blue, as he has been referred to over the decades was more than just a musician, he made jazz smooth, sophisticated wore tailored suits, and made it cool for men to wear scarfs. Every photograph of Davis from the 1950s-60s shows a man who’s style is never out of place. He always had style, class, and poise whether he was playing on stage, or just lounging. Miles Davis earned his name as a King Of Blue and his place on our list.

4. Brian Jones

The founder, and the principal songwriter of the now legendary band “The Rolling Stones”, Brian Jones, was by far the most stylish of the group. He was an avid blues lover, and was a major influence in bringing acts, like Howlin’ Wolf to the U.K. Jones was always immaculately dressed, no matter if it was sharp Mod style of the early 1960s or a flamboyant Peacock Style of the latter part of the decade, Jones would always get it right. He was always in either razor shape suit tailored to his frame, or in a causal. His friend, antique dealer, and editor of Men In Vogue Christopher Gibbs remembers: Brian did absolutely love dressing up. He had a tremendous lot of clothes, and spent an awful amount of time preparing himself for late-night forays into the clubs.“ Until the day he died Brian Jones was, and still remains the most stylish member of The Rolling Stone

3. Bob Dylan

The man who made peacoats, chelsea boots, and wayfarers cool for an entire generation, and was one of the most influential voices of the 1960s. Dylan was born Robert Allen Zimmerman in Duluth, Minnesota, but spent his childhood in Hibbing, Minnesota. Dylan was always rebellious, he spent his early years sneaking off to listening to various blues, and country stations broadcasting all the way from Shreveport, Louisiana. As a teen, he saw the film The Wild One, and that made a lasting impression on his style, which would become the blueprint for his style and the style rock generation.

2. Sam Cooke

Sam Cooke has one of the most recognizable tenor voices in popular music, he is one of the most influential singers of all time, and is the man who is credited for single handily creating the musical genre we call “Soul” music. Not only did he rack up over thirty Top 40 hits throughout his career, but he did it all with style like no other. Sam Cooke dominated the charts and crossed over partly due to his charm, looks, and style. (This is not to say his talent took a back seat, but it complemented all the rest.) Sam Cooke was the blueprint that all Soul singers followed from the cut of his finely tailored suits to the way he cut his hair. When it comes to style few had it like Sam Cooke, in his lifetime The Beatles wanted to tour with him, men wanted to be him, and women wanted to be with him. He stood out as the proper gentleman with not a cuff, or crease out of place.

1. Jimi Hendrix

The life Jimi Hendrix is an extraordinary fairytale like no other, born Johnny Alan on November 27, 1942, but was changed to James Marshal Hendrix by his father to honor his brother he lost in WWII. Hendrix grew up in poverty in Settle, Washington, and with the inability to purchase a properly fitting pair of clothes, or shoes did not stop a young Hendrix. With a meager budget to work with it here where he learns to mix and match clothing items to create a style all his own. After a short stint in the army, Hendrix went on the road as a backing guitar player for the biggest soul acts of the day, including, Sam Cooke, and it is here where he sharpened his style and honed his guitar chops. He soon quit, and went out on his own moving to New York he furthered his style of both playing, and fashion when he started being a regular in Greenwich Village. It is here that one of his biggest musical, and style influences, Bob Dylan. Hendrix was the heart of Woodstock and he remains almost inarguably the best electric guitarist of all time. Then he was discovered, and shipped to England. As they put a band around Hendrix, the management started to through around ideas about his image, and when it came to his own image there was no one that understood that better than Hendrix. In a time before celebrity stylists, and most artists had to bring their “A” game to their style. With years of practice in mix match clothes as an impoverished youth, Hendrix cashed his first check and hit the streets in search of vintage style. He shopped British boutiques like Granny Takes a Trip (the kindling for designers Vivienne Westwood and Paul Smith) , and I Was Lord Kitchener’s Valet (the stomping ground of greats including Eric Clapton, Mick Jagger, and The Beatles). The spree was successful in unearthing two antique army uniforms, which became staples of his early career.