A friend of mine had enrolled his daughter in a Beit Yaakov school in a small Israeli city. He was called by the principal, who informed him that his daughter was being suspended. When he asked for the reason, the principal said "It's a problem with the way she dresses." "What is the problem?" "She wears a maxi-skirt. Our rule is a knee length skirt or dress". "But maxi should be better! What's the problem" "We can't tell if she is wearing the right stockings!"
Conformity seems to be the key word in most communities. My wife, and some of the other women in my family, resist the trend to sheitels (wigs) and wear head scarfs. Their feelings are that scarfs are more modest, more comfortable, and there is no need to take out a second mortgage in order to buy one. Yet, people do talk behind their backs saying that "they apparently don't care about their appearance". That this is lashon hara should be obvious. But they don't see it as such because they feel that my wife (and others) are violating a community standard. The attitude of many is that "if you are more lenient than I, you are not a good Jew. But if you are more strict than I, you are a fanatic rebel". A good friend asked me several years ago about this attitude. I said "You must do what you feel is right. At some point, you must choose between the community's values and G-d's values, as you understand them." He said "Every other rabbi I have ever spoken to, has said that you can't come to G-d without following the community!"
Another problem is the desire to maintain a certain type of community. While most Jews are happy that someone has chosen the path of Torah, there is still a malaise at what they will be bringing into the community. People don't what what they have built "watered down". Way back when I was single, it was not uncommon for the parents of a young "frum from birth" woman to forbid their daughter from dating me, as I am a baal teshuvah. I even had the horrible experience of meeting a girl's parents,and having them get up and walk out of the room when they learned of my background. I had a bit of a karmic "pay back" when some twenty years later, a grandson of those parents became my student! (I never mentioned it to my student, though.) I did not let these things deter me from my chosen path. I will not allow people to decide my worth and make decisions for my life. We are answerable to G-d, not to sociology.