Abstract This study examines the historical development and religious significance of head covering (gilui rosh) practices in Jewish tradition through comprehensive analysis of biblical, Talmudic, and post-Talmudic sources. The methodology involved systematic examination of primary religious texts, including the Hebrew Bible, Babylonian and Palestinian Talmuds, medieval codifications, and rabbinic responsa spanning from ancient times through the 17th century. The research reveals that contrary to popular assumptions, no biblical commandment requires head covering, and early Talmudic sources indicate that bareheadedness was commonly accepted among Jewish men in Babylonia during the compilation period. The practice of consistent head covering emerged gradually as a custom rather than law, initially associated with scholarly dignity and extreme piety. Medieval sources demonstrate significant regional variations, with Spanish Jewish communities adopting stricter observance influenced by Islamic customs, while French and German communities maintained more lenient practices. The study traces how post-Talmudic authorities increasingly codified head covering requirements, particularly during prayer and religious study, though dissenting voices like Rabbi Solomon Luria argued no prohibition existed. Key findings indicate that the evolution from custom to perceived religious obligation occurred through rabbinical interpretation rather than scriptural mandate. The research concludes that head covering in Jewish practice represents a modus vivendi that acquired religious significance through historical development rather than originating from divine commandment, providing important context for understanding contemporary variations in observance across different Jewish movements.