When Do Jewish Boys Begin to Wear Their Tallit?

"Many point to the fact that the verse in the Torah “if a man shall take a woman . . . ” immediately follows “you shall make for yourself fringes.” (Deuteronomy 22) This juxtaposition serves as basis for the custom that people begin wearing the large tallit only after marriage."

This is from the Maharil bederech drush, but not a Halachic reason. I'll also argue that if you go further in "if a man takes a wife" the fuller context is "if a man takes a wife and he hates her." To suggest that one only wears a Tallis if one intends to marry a woman he hates sounds just plain silly.

The real reason today we don't wear it until marriage is because socially it's a challenge.

From OpenSiddur:

Tallitot stripes and the use of lines in clothes is an ancient Jewish style, found in archeological diggings from the time of Bayis Sheini . It may have originated from Yosef’s Ketonet Pasim. There was no uniform standard in Ashkenaz for the color of the stripes, and in Worms, the Baal Tefilla wore a c Reply

In the mostly-Conservative community of Ashkenazim and Sephardim in which I grew up, the tallit kattan was commonly called "tsitsis", and the tallit gadol came in two sizes: the size of a woman's rectangular shawl, and a version that was longer and whose width covers a man from his neck to his knees. The first was more common, was found on every synagogue's loaner rack, and was sometimes called a "bar mitzvah" tallit because they were commonly given to bar-mitzvah boys by their grandmothers. The second was called a "wedding tallit" because it was often given to a man to serve as the chuppah at his wedding and to wear afterwards. Boys began wearing tallits around age 10 when they were called up to lead or read during children's services (often part of bar mitzvah prep), and full time once bar-mitzvah.
Furthermore, my father taught me that a man should be buried in his father's tallit so he could find his father in heaven. Reply