Jesus did NOT conform to the status quo of his culture - ON IMPORTANT ISSUES. 
Jesus spoke with the Samaritan woman at the well AND asked her for a drink. That was taboo! 
Jesus - a spiritual authority - dined with tax collectors and prostitutes. Again - taboo in his Jewish culture.
Jesus' disciples didn't follow the proper cleansing ritual before eating. Taboo too.
 . . . . . . On down the line.

Jesus wore sandals - cause that's all he had -there were no Gucci slippers available.

Jesus DID NOT have to pick only men for his apostles - but He did. Whenever there was an important issue to deal with - Jesus always SET the standard - regardless of what others would think!