According to Wright and Guy (p. 100 in True, et al., A Passion for Antiquities: Ancient Art from the Collection of Barbara and Lawrence Fleischman) "The Attic chous is a specific shape of oinochoe created especially for the three-day festival of the Anthesteria, held in the spring in honor of Dionysos. On the first day, the Pithoigia, the new wine was opened and tasted. On the second, the Choes, the three-year-old male children of Athens were enrolled in their fathers' phratries (kinship groups)... On the third, the Chytroi, vegetables prepared in cooking pots were offered to Hermes Psychopompos, who conducted the souls of the deceased to the underworld. On this day, the spirits of the dead were free to return from the underworld and roam among the living; they were sent back at the end of the day by the exhortations of the festal participants".
The present chous is of the standard size used for the drinking contests that took place on the festival's second day. The festival also included musical performances, as depicted here.
On Anakreontic revellers, Boardman informs (Athenian Red Figure Vases, The Archaic Period, p. 219) that "Transvestite men wearing chitons, mitra-turbans over their hair, and sometimes carrying parasols, appear in some scenes from about 520 on. On a Kleophrades Painter vase with such figures one holds a lyre labelled Anakreon, the Ionian poet who came to Athens in about 520 and who may have introduced this drag performance which remained fashionable for over fifty years. The headdress was suitable for men in Lydia but could only have been regarded as effeminate in Athens. Anakreon's poetic view of the good time (euphrosyne) is very much that of the red figure symposion. He died in Athens soon after Marathon, aged eight-five, choked by a grape pip, they said."
Beazley listed the Painter of Florence 4021 as a follower of the Pistoxenos Painter (Attic Red-figure Vase-painters, 873-874). For another chous by this artist with the same ornament framing the scene and handle see no. 92 in Moon, Greek Vase-painting in Midwestern Collections.