Who Ever Said Jazz Had To Be Drab?


Cassandra Wilson

This Grammy-winning, Mississippi-born songstress always strives for red-carpet elegance when she graces the stage. Blessed with a curvaceous figure, radiant skin and smile, Wilson channels the glamour of divas such as Sarah Vaughan and Nancy Wilson while topping it off with a modern twist with her signature sun-kissed dreadlocks.



David Sanchez

David Sanchez is a tenor titan with a sinewy body built for the runway. It’s no surprise that Banana Republic plucked this Puerto Rican saxophonist for its 2009 “City Stories” campaign. Oftentimes, there’s an athletic swagger to his dress code, sometimes hinting at those 50s Italian suits that Miles Davis wore which accentuated his boxer’s physique. And even when Sanchez dresses casually, there’s an undeniable machismo to his swag.

Esperanza Spalding


Bassist/singer phenom also rocked urban sophistication in the same Banana Republic “City Stories” campaign. Often seen flashing an incandescent smile and a mushroom cloud shaped afro, Spalding channels early-’70s Minnie Riperton (sometimes even back to the Rotary Connection years), effortlessly, while also making sure her style isn’t too throwback a la neo-soul mimicry.

Greg Osby


Forward-thinking alto saxophonist, composer and bandleader Greg Osby always goes for a no-frills, natty look when he hits the stage. Strutting with a vintage Fedora hat and smart eyewear, Osby’s crisp fashion sense epitomizes the timeless modernity associated with the well-dressed jazz saxophonists.

Gretchen Parlato


This pint-sized breakout jazz singer of the year shows that you can grace a nightclub stage without getting all stodgy ballroom gown with it. Never too flashy, there’s always a spunky coyness to her attire that reminds people that a new younger generation of jazz artists is indeed emerging.



At the risk of playing into a cliché, this pianist plays the way she looks―as if she’s some superhero from a Japanese anime flick with a multicolored asymmetrical hairdo and 21st-century “on-the-go” attire. She's always energetic and cutting-edge. Not too many jazz artists can get away with Hiromi’s daring style, but on her it looks ideal if not iconic.

Theo Bleckmann


No other jazz singer gives you nerd chic like German-born Theo Bleckmann. Far more envelope-pushing than any hipster with a signature look that surpasses merely trendy, Bleckmann makes “being smart” look sexy, whimsical and adventurous.

Robert Glasper


If there is anyone whose look epitomizes the jazz musician of the hip-hop generation, it is Texas-born pianist/composer Robert Glasper, who takes fashion cues from various eras and musical genres and contextualizes them into his own signature bo-ho look, which juxtaposes hip-hop swagger with jazz’s cool detachment.

Lizz Wright


Georgia-born singer and songwriter Lizz Wright strikes the perfect balance between dressing sassy and sophisticated but never slutty. With her statuesque physique and a shy, girl-next-door allure, she gives a new template for how modern jazz divas should dress.

Leo Tardin


Swiss-born pianist/keyboardist Leo Tardin puts a hipster twist to his fashion sense without it being painfully ironic. Often seen peacocking around in plastic, clear-colored glasses, a skinny tie and monochrome pants and shirts, he’s already nailed down an iconic look to call his own without being too obvious about it.

Joshua Redman


Had he not been a jazz musician, saxophonist/composer Joshua Redman could have easily landed a job as a model. It’s no coincidence that he once endorsed Donna Karan in the ’90s as he wore well-tailored suits that reminded everyone how to “dress to impress.” Debonair to a default, Redman simply knows how to rock a suit.

Miguel Zenón


Bald, baby-faced and apparently brilliant―according to the MacArthur Foundation, which granted him a 2008 “genius” award―the Puerto Rican alto saxophonist exudes an urbane sophistication with a fashion sense that's street-wise, contemporary and always well put together but never fussy.

Dianne Reeves


Top-ranking jazz singer Dianne Reeves has a look that never goes out of style. Carrying on the regal tradition of Ella Fitzgerald, Sarah Vaughan and Carmen McCrae, Reeves’ “easy on the eyes, knowing-how-to-age-gracefully” flair exudes comely confidence.

Stefon Harris


Youthful ebullience and erudition typify both the music and look of vibraphonist/composer Stefon Harris. He has an “always tight” style that works on the bandstand, in a nightclub or in a posh hotel cocktail lounge.

Jason Moran


“Southern comfort” is the best description for pianist/composer Jason Moran, who opts for well-tailored blazers and top-line shirts versus “off the rack” suits. His look often suggests the young jazz lions of the '80s and '90s, but there’s an elusive X-factor that also puts some distance between him and the rest of the pack.

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