In the Gospels, Jesus didn't care about the social norms. He consulted with the unclean, the sinners, and the infirm. Jesus reached out for any who would come to listen. He accepted anyone who believed and had an honest heart. He healed the servent of a Roman centurion, an oppressor, because he had the faith to come to him.
He taught that anyone could be saved if the loved God and believed in him. He told the story of the Good Samaritan to a crowd. Of the three men who pasted by an injured man only a Sameritan, unclean by Jewish custom, helped the man. Jesus also travelled into and met a woman at a Sameritan town. Talking to a woman in public was unacceptable at the time, a Jew talking to a Samerian was frowned upon, and this woman had become a social disgrace having been divorced and remarried several times. Still Jesus spoke with her as an equal and through her converted an entire town.
Jesus sought places of quiet purity and not external holiness. He went into desrts and onto mountains to listen and pray. He taught against load public prayers to get attention for oneself. He told a parable of a taxcollecter, a job which made people hate you for siding with the Romans, and extorting money, and a Pharisee. The Pharisee prayed loadly of his on goodness, while the taxcollecter stood at the back of the temple and quietly prayed,"Lord forgive me a sinner." Jesus asked the crowds who was the one who prayed better and the crowds answered the taxcollector.
Jesus had such a following because he spoke to the people in common terms and of redemption, not laws.
He spoke to fishermen of fishing, sheperds of sheep, and of other similar things. He spoke not of laws but to people's hearts. He gave people exactly what they needed, hope.