The way I see it, there are two different types of people: those who think being true to themselves is only natural, and those who view it as a death sentence. Don't get me wrong, the decision to either cover up or be open is an extremely difficult one. Neither situation is easy, no matter who you are. Insecurity exists either way. It's only natural. Still, originality is something that most people value (and even envy), whether or not they admit it.
I've seen people get criticized for "wearing a mask." They're taking the easy way out, people will say. Yes, for a great many people, it is easier to forget who they are than take the risk of being shut out because of it. However, even after they make themselves into the person they think everyone wants them to be, the insecurity never goes away. What if someone sees through me? What if they still don't like me? Why am I still so miserable? Abandoning their sense of self may make it easier for them to fit in, but that in no way makes the process itself easy. There is always the threat of a slip-up or someone seeing through their facade, no matter how calculated. Just as with a lie, the act can become too elaborate to keep track of. The most accurate way I can find to explain what I mean is in this quote from Mark Twain: "If you tell the truth, you don't have to remember anything." Being "the man behind the curtain" gets exhausting after a while. Believe me, I've lived it. One thing I can promise you: there will be a Dorothy one of these days to draw the curtain back and leave you feeling exposed.
On the opposite end of the spectrum, there are those who would rather stand out to the point where they get strange looks when they go out in public than put their own self-worth on the backburner. BlackFriday, a profoundly goth YouTuber, is one of these people. In one of her videos, she dressed up in "normal" clothes and filmed herself walking around her hometown in Germany. She mentioned that she was not getting stared at as much as usual and fitting in more, but immediately said that it felt extremely uncomfortable. "I'm not standing out in the way I want to stand out," she says after leaving a crowded Starbucks. "It's like Halloween, except I'm scaring myself."
No matter what, I hold this opinion to be true: you should never make anyone feel ashamed about how they choose to carry themselves. Coming into one's own is a process, and it's all a part of growing up and finding what makes him or her most comfortable. I see too many people who tell others how they "should" act or "should" look. The fact is, no amount of "should" is going to change the way a person wants to live their lives.
As the kids say, "You do you." Let them do them.