It is certain that Jesus, a Jew residing in the land of Israel in the first century, did not wear a kippah (skullcap).
The custom of wearing a kippah arose in Babylonia between the third and fifth centuries C.E. among the non-Jewish residents—Jewish residents of Babylonia had not yet adopted this custom, as the Dura-Europos frescoes show—and passed from there to the Jewish community of Europe.
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For more on Jesus’ clothing and appearance, check out these JP articles:
◦ Marvin R. Wilson, “The Appearance of Jesus: Hairstyles and Beards in Bible Times”
◦ JP Staff Writer, “Tangled up in Techēlet: Tzitzit (Ritual Tassels) in the Time of Jesus”
To read more New Testament insights from professor Shmuel Safrai on Jerusalem Perspective, click here.