Male Hair Dyeing
Parshat כי תצא has the commandment against cross-dressing. We are taught that women should not wear men’s garments, nor should a man wear a woman’s dress. Included in this Halacha, is that a man is not allowed to color his hair. This is viewed as something typically done by women. It’s also written, that when a man begins to age, he should not pluck his grey hairs. There was a case brought in אגרות משה, that was a book of Halachic questions posed to Rav Moshe Feinstein. A young man who worked in a bank had his hair grow grey in a bizarre manner. Half of his hair was white, and the other half dark. People would stare and make fun of how he looked. He was given a Heter to color his hair by Rav Moshe. The banker had no intention to act in an improper way. He wanted to follow Halacha , but he did not wish to be a laughing stock. He was bailed out by Rav Moshe.