Louis Armstrong

By the late '20s, Armstrong's influence as a trumpeter and vocal stylist was central to what jazz was and would become. According to the writer Albert Murray, by the early '30s, his celebrity and status as a culture hero had men across the United States imitating his dress style, too.

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Captions by Greg Thomas

Duke Ellington

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Ellington, an icon of sophistication and elegance, was arguably the greatest American composer of the 20th century. His music had a cosmopolitan flair that reflected Negro American life and national values; his charm and nonchalance seduced audiences and fine ladies across the globe.

Billie Holiday

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Lady Day’s extension of the styles of Louis Armstrong and Bessie Smith had a blues-tinged sadness, yet was suffused with determined resilience. The gardenia in her hair was there to show beauty despite the pain of life. Her sound is forever etched into the footprint of the evolution of jazz.

Lester Young

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The “Prez” of the tenor saxophone’s pork-pie-hat-wearing, sax-tilted-to-the-side style became a prime example of cool in American culture. But outer fashion pales in comparison to the influence of his melodic, deeply individual instrumental approach had on the course of jazz improvisation. 

Billy Eckstine

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Through his deep baritone and handsome looks, Eckstine became the first popular American romantic balladeer who was also black. His early-'40s big band led a transition from the swing era to bebop. Eckstine's design of a high-roll collar that formed a "B" over a Windsor-knotted tie was known as the "Mr. B. Collar."

Dizzy Gillespie

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Gillespie's fashion style at the advent of bop in the 1940s — soul-patch goatee, beret, black horn-rimmed glasses, clean double-breasted suits — became a hip trend that underscored the power and influence of his trumpet wizardry and leadership of a modern movement in jazz.

Hazel Scott

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A piano prodigy, Scott became famous for "swinging the classics." She also appeared in Hollywood films and, in 1950, briefly became the first woman of color to have her own television show. Her beauty and sense of style was icing on the cake to her excellent musical talent.

Miles Davis

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His tender sound on trumpet graced several of the most popular albums in jazz, including Kind of Blue in 1959. Esquire magazine featured Davis as a model of sartorial cool in 1960, when custom-made preppy or Italian-styled suits were his norm. Later, he took a page from the psychedelic '60s.

Abbey Lincoln

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The sexy chanteuse here soon transformed into a proud representative of the movement for civil and human rights who, along with then-husband Max Roach, screamed for justice on We Insist! Freedom Now Suite. She donned an Afro and cornrows in later years as her artistry grew in expressive depth.

Roy Haynes

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Still hip at 86, Haynes was featured in Esquire in 1960. His custom-made suits — then from the Andover Shop in Cambridge, Mass. — fit his 5-foot-4-inch frame to a tee. Today, whether swingin' the drums, driving classic sports cars or appearing in the Grand Theft Auto video game, he's timeless.

Wynton Marsalis

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After rock, fusion and disco changed the dress styles of many musicians, Marsalis came along in the early 1980s with fiery dedication to a classic style of jazz performance and dress. His excellence and distinction appealed to a luxury watchmaker — he's been an "ambassador" for Movado for more than a decade.

Dianne Reeves

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Perhaps the premier jazz song stylist of our time, Dianne Reeves is both sultry and elegant (as in the movie Good Night, and Good Luck) and earthy and ancestral, as she is here in a kente cloth outfit. She's living proof that jazz and style are modern and classic at the same time.