As if we've interrupted him, the sitter points to a specific spot in his book with his right index finger, marking his place. We don’t know what he’s reading, but the book’s size and gold-edged paper suggest poetry, signaling that he’s a man of culture.

The walls provide a smooth backdrop and form an angle that sets off the complex silhouette of the cap, whose prickly gold decorations were known as ciondoli.

Unlike the other two masks embedded in the furniture, this “face” made out of folds of fabric at the sitter’s groin offers a subtle provocation. Could it be a sly commentary on the relationship between masks and portraiture?

This type of fitted, elegant doublet, or giubbone, became popular at Cosimo’s court, especially in the 1540s. The technique of slashing fabric to create a jagged outline was fashionable among elite society, part of an attitude known as sprezzatura, or nonchalance.

Even with pearls, gold bracelets, and two rings, Cassandra’s most stunning piece of jewelry is an elaborate belt embellished with masks and ornaments. We know the duchess Eleonora commissioned a gold belt with masks in 1545, so this was definitely the look of the day.

The eye-catching drape of sheer, green-striped organza silk falls magically behind Cassandra. While drapes were common in portraits, this silk’s unique character may be a nod to Cassandra’s maternal family, who were major silk manufacturers and merchants.

This fashionable sitter, identified as Cassandra Bandini, wears a yellow satin dress with a long, red overdress, known as a zimarra, with velvet trimming and a pattern of large branches. Records show that the zimarra was Duchess Eleonora’s favorite type of garment.

Francesco Guardi was 15 or 16 when imperial troops laid siege to Florence in 1529 to reinstate Medici rule. Dress codes were eased for those who followed their fathers on patrols but were too young to fight, which explains why he’s a bit overdressed.

The badge on Guardi’s hat shows Hercules, the mythical hero associated with Florence and later adopted by Cosimo as a Medici emblem. The depiction of Hercules finding his strength to defeat the giant Antaeus would have been inspirational for a young Florentine.

The pole-like weapon in Guardi’s right hand is either a halberd, a roncone, or a coresque. In any case, it was largely ornamental because he was too young to fight.

A traditional symbol of fidelity, the spaniel is appropriate in a picture commemorating a marriage.

The string of black beads cascading across the sitter’s lap is typically interpreted as a rosary, but it’s more likely an extension of the beaded belt around her waist—a fashionable accessory also favored by Duchess Eleonora.

There’s evidence that this sitter is Cosimo de Medici’s aunt Francesca Salviati, who married Ottaviano de’ Medici. The dominance of her family’s colors in the composition—red and white—support this identification.

The necklace’s motif of paired cut branches might signify two branches of the Medici family joining in union.