As you see from these portraits, there is a considerable history of men wearing pearls throughout history to signify their importance. 

From the Qing dynasty in China, there is the Yongzheng Emperor and the Maharaja Bhupinder Singh of Patiala in royal pearls.

The first evidence of pearls being worn by royalty was in the Song dynasty of Chinese rulers 2300 BCE. Indian royalty, Henry VIII wore pearl embroidered clothing and other English kings, and Julius Caesar and many more were the Men in Pearls of history. English knights would carry a pearl into battle for an important talisman of strength and success. Pearls were originally a man's domain.

For contemporary men in pearls don't seem that outrageous. For them it's not a statement of femme or even androgyny. The NYTimes recently published an article, Pearls are a Boys Best Friend that highlights some of the players in the 2020 Mens Fall Collections and other fabulous men wearing pearls as a distinctive accessory. "Pearls are hard yet smooth, timeless yet trendy, iconic yet rare-offer an introduction to style that allows the wearer to have it both ways."

Pearls are "a silky orb that lives inside an armor of rock-hard grit." How's that for a men's description of a pearl?