Earrings begin to appear on portraits of women and girls in Italy again around the first quarter of the 16th century, nearly 900 years after the early medieval Lombardic earrings.
Unlike France and England, there do not seem to be many Italian men who wore earrings in the 16th century.
- Portrait of a girl by Sebastiano del Piombo, c. 1515
- Portrait of a young lady by Bartolomeo Veneto, 1520s
- Portrait of a lady by Bernardino Luini, c. 1525
- Portrait of Laura Pisani, 1525
- Venus by Bernardino Luini, c. 1530
- Portrait of a young woman by Titian, 1530s
- Antea by Parmigianino, 1530-1535
- Portrait of a lady by Pieter de Kempeneer
- La Bella by Titian, 1536
- Portrait of Isabella d'Este, Duchess of Mantua by Titian, 1536
- Portrait of Eleonora Gonzaga by Titian, c. 1538
- Venus of Urbino by Titian, 1538
- Portrait of Camilla Gonzaga with her three sons by Parmigianino, c. 1539-1540
- Portrait of a young woman and her little boy by Agnolo Bronzino, c. 1540
- Portrait of Bia de Medici by Agnolo Bronzino, c. 1542
- Eleonora of Toledo by Agnolo Bronzino, 1543
- Portrait of Eleanor of Toledo with her son Giovanni de' Medici by Agnolo Bronzino, c. 1544-1545; also, Eleonora of Toledo and her son by Agnolo Bronzino, c. 1545-1550
- Portrait of a girl by Titian, c. 1545
- Portrait of Giulia Varano, Duchess of Urbino by Titian, c. 1545-1547
- Portrait of Eleanor of Toledo, c. 1550
- Portrait of Isotta Brembati Grumelli by Giovanni Battista Moroni, c. 1550
- Profile portrait of a young woman by Sofonisba Anguissola
- Portrait of Countess Livia da Porto Thiene and her Daughter Deidamia (also here) by Paolo Veronese, c. 1551
- Portrait of Maria de' Medici by Agnolo Bronzino, 1551
- Young woman with a dish of fruit by Titian, c. 1555
- Portrait of a lady (La Dama in Rosso), perhaps Contessa Lucia Albani Avogadro by Giovanni Battista Moroni, c. 1555-1560
- Portrait of Bianca Ponzoni Anguissola by Sofonisba Anguissola, c. 1557
- Portrait of an unknown lady (The Lady in White) by Titian, 1560
- Portrait of Eleanor of Toledo by Allesandro Allori, c. 1560
- Portrait of Eleanor of Toledo by Agnolo Bronzino, 1560
- Portrait of Lucrezia de' Medici by Agnolo Bronzino, 1560
- Portrait of Sofonisba Anguissola by Lucia Anguissola, 1560-1565
- Portrait of a woman by Bernardino Campi, late 1560s
- Portrait of a young woman by Giovanni Battista Moroni, c. 1560-1578
- Portrait of a woman by Giovanni Battista Moroni, c. 1564-1570
- Portrait of a lady in a plumed hat, c. 1565-1575
- Portrait of a lady by Jacopo Zucci, 1570s
- Portrait of a woman by Alessandro Allori, 1570-1590
- Portrait of Eleonora di Don Garzia di Toledo di Don Pietro dei' Medici by Alessandro Allori, c. 1571
- Portrait of an African woman by Annibale Caracci, 1580s
- Portrait of Bianca Cappello by Alessandro Allori
- Portrait of a lady of the court by Lavinia Fontana, 1590
- Portrait of Marie de' Medici by Pietro Fachetti, c. 1593-1595
- Miniature portrait of Marie de' Medici
- The Penitent Magdalene by Caravaggio, 1594-1596; see detail
- Judith Beheading Holofernes by Caravaggio, c. 1598
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