„Never judge a book by its cover" - judging people based merely on looks, the way they dress would be inappropriate, because it doesn’t have to reflect their personality all the time.
People represent many styles like punk, hippies, old-school, hipsters, pop and so on. The way they dress can also represent the music they are listening to for example rock and hip-hop. Other people just want to look different than the others, so they come up with something new, extreme so they feel special. But after a while it can turn out badly, because if somebody takes interest in the way that person dresses, he/she can copy it then a new style is made and the person, who came up with it, has to find another way to be special.
On the other hand we can also talk about people, who don’t care about how they dress. They just want to feel comfortable in something and they “hide their personalities”, so you have to meet and get to know that person to see who he/she is. In a way it can be considered good, but in my opinion, it is hard for them to make new friends, because nowadays people judge a person by how he/she is dressed.
In my opinion, you have to find yourself and what fits you and what’s good for you, and most of all, feel self-confident. When you see people that are self-confident, they radiate some kind of good energy. When you look at iconic people, most of the time they are dressed up exactly the same way for all their life. They dress for themselves. I think the purpose is to find what’s right for you and what you feel good in. When somebody tries to be someone else and looks too much to the newspaper or wants to resemble a certain girl, it will be a failure because this person is not this girl. It’s better to spend some energy to find, “ok, this is good for me,” or “this is the right thing for me”.