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Bronzino got his chance with the Medici at their wedding in 1539, when he painted decorations for the marriage of Duke Cosimo I to Eleonora di Toledo, a Spanish noblewoman not yet twenty. Cosimo liked the work enough to hire him outright, and Bronzino stayed the family's court painter for the next twenty-five years.

His portrait of Eleonora with her young son Giovanni, painted around 1545, shows her in a dress patterned with pomegranates against a background of lapis lazuli blue, the same expensive pigment usually reserved for the Virgin Mary's robe. Every fold of fabric is rendered so precisely it looks almost cold, a deliberate style: Bronzino's Medici portraits present rulers as composed and controlled, never caught off guard.

He also decorated Eleonora's private chapel in the Palazzo Vecchio, his first major commission for the family, and kept painting Medici portraits until his own death in 1572, ten years after Eleonora herself had died.