Billie Holiday's Most Elegant Beauty Moments

By Larry Stansbury · Updated April 7, 2025

When Billie Holiday stepped onto a stage, it wasn’t just her voice that turned heads—it was her presence. Known as Lady Day, she embodied a timeless kind of beauty that can’t be replicated—only revered. More than a jazz icon, Holiday was a blueprint: her look, her poise, and her unapologetic elegance still inspire generations of Black women who understand that beauty is as much about soul as it is about style.

In the 1940s, the Velvet Mood singer was known for wearing deep, dark lipstick that made her gardenia-adorned hair pop even more. Her brows were always arched to perfection, and her lashes? Flirty, feathered, and unforgettable. At times, she liked to keep it cool and covered with a head wrap, always exuding that effortless kind of glam. In 1939, she posed for a now-iconic photoshoot, gardenias in full bloom—but it’s the lashes and that soft gaze we’re still drawn to.

Fast forward to 1947, when the Lady Sings the Blues legend hit the stage at Manhattan’s Downbeat Club. No foundation, no powder—just bold lipstick, natural skin, and star power.

By 1957, Billie switched things up for her performance at the Newport Jazz Festival, leaving the gardenias behind but keeping the signature red lip. And through it all, she never shied away from the camera. New headshots, new angles—because loving yourself is always in style.

In honor of the late icon, we’re celebrating some of Billie Holiday’s most unforgettable beauty moments.