Why do most American Orthodox men wait until marriage to don a tallit, when their European predecessors wore prayer shawls from childhood? This stark divergence stems from a critical misreading of Talmudic sources in Kiddushin 8a and 29b, which actually discuss head-covering rather than the wearing of the garment itself. Through detailed analysis of these passages, along with Rashi's commentaries and the Shulhan Arukh's codified law, a clear picture emerges of how this prevalent American custom developed without solid halakhic foundation. While the Maharil attempts to link tallit-wearing to marriage through biblical verse proximity, mainstream halakhic authorities, including the Shulhan Arukh and Be'er Hetev, explicitly mandate tallit use for all males from bar mitzvah onward. The traditional Western and Central European practice, where even pre-bar mitzvah boys wore tallitot, aligns more closely with these authoritative sources. Given these findings, a return to universal tallit-wearing among post-bar mitzvah males would better reflect established halakhic principles.