1) We have hadiths that it is recommended to pierce the ears of a newborn. However, scholars have understood this as just piercing the ear, and not wearing and earring for an adult man. Secondly, if something is considered socially inappropriate (and makes one associated with a negative culture), then a believer is required to avoid that.
2) I am not aware of a hadith that says any of the Imams had earrings when they were adults.
Now in the USA, honestly, wearing earrings is associated with a negative culture. That’s why most American professionals, officials, and people respected in their communities don’t actually ear earrings.
In addition to that, in our era, earrings are considered a feminine adornment in most societies, and we have hadiths that prohibit men from appearing like women.