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Pilei

Pilei or freedom caps (plural of Pileus) are soft conical caps worn by the Dioskouroi and freed slaves.  Pilei and with stars above them are frequently used to represent the Dioskouoi.  Pilei also represent freedom because freed slaves wearing pilei would follow their former master in his bier at his funeral (demonstrating his magnanimity and bringing him prestige). 

 

Pilei

Pileus (plural of Pileus) , bonnets, or caps, of woven wool, sometimes called freedom caps.  Pilei (plural for pileus) and pilei with stars above them are frequently used to represent the Dioskouoi.  Pilei also represent freedom because freed slaves wearing pilei would follow their former master in his bier at his funeral (demonstrating his magnanimity and bringing him prestige).  The form of the Roman pilei was varied; some were round, others resembled a helmet, some were shaped almost like a pyramid, and some were of a more depressed form.  The Romans for he most part went without hats, except on religious occassions, the saturnallia, or when on journies or military service.  The pileus was also sometimes worn by the sick, old men and newly freed slaves (the latter in token of liberty).