Events from the year 1558 in art.

• Benvenuto Cellini begins writing his influential autobiography, focusing not only on his life but on his goldsmith's art, sculpture, and design.
• Juan Bautista Vázquez the Elder returns to Avila to complete the altarpiece at the Monastery of Santa Maria de las Cuevas, left unfinished by Isidro de Villoldo.

• Pieter Bruegel the Elder – Landscape with the Fall of Icarus
• Pierre Reymond – Tazza: Scene from the Book of Proverbs
• Domenico Campagnola – Callisto's Transformation into a Bear after Giving Birth to Arcas
• Tintoretto – Saint George and the Dragon
• Titian - Crucifixion
• Paolo Veronese – Assumption of the Virgin

• January (or February) Hendrik Goltzius, Dutch printmaker, draftsman, and painter (died 1617)
• December 3 - Gregorio Pagani, Italian painter active mainly in Florence (died 1605)
• date unknown
  • Giovanni Alberti, Italian painter (died 1601)
  • Baldassare Croce, Italian academic painter and director of the Accademia di San Luca (died 1628)
  • Honami Kōetsu, Japanese craftsman, founder of the Rinpa school (died 1637)
  • Dirk Pietersz, Dutch Golden Age painter (died 1621)
  • Juan de las Roelas, Seville-based painter (died 1625)
  • Gregorius Sickinger, Swiss painter, draughtsman, and engraver (died 1631)
  • Jan de Wael I, Flemish painter of the Baroque period (died 1633)
• probable
  • Belisario Corenzio, Italian Mannerist painter (died 1643)
  • Chen Jiru, Chinese landscape painter and calligrapher during the Ming Dynasty (died 1639)

• January 24 - Gerlach Flicke, German limner and portrait painter working in London
• August 15 - Paul Lautensack, Germain painter and musician (born 1478)
• date unknown - Scipione Sacco, Italian painter of the Renaissance active in Cesena (born 1495)
• probable
  • (died 1555/1558): Giovanni Francesco Caroto, Italian painter active in Verona (born 1480)
  • (died 1555/1558): Benedetto Montagna, Italian engraver (born 1481)