Maybe it’s shallow, but yes, I do look at how people present themselves to the world. Their appearance. I wonder what they are trying to communicate, and there are two sides to every story:

Someone who dresses well, and is nicely put together may be someone who cares about their life, who wants to dress up for it, who wants to use it as an opportunity to express. They breathe in every moment, every detail. The way the details make up the larger picture. They choose carefully, sometimes daringly. They know the way you dress the part can impact the way you play the part. They are conscious, maybe conscientious.

Or they may be insecure, wearing the layers of trends as a disguise. They’re not using fashion to stand out, but to blend in, or disappear. They make sure not to step out of the box. They are afraid to be seen - to be really seen.

Someone who throws on a t-shirt, some pants, flip flops, and looks disheveled may also be one of two things:

They may be someone who is so engulfed in life, pursuing their passion, and ambitions - whether they’re a working student or the CEO of a fortune 500 company - they don’t have time to get wrapped up in silly details such as what matches with what. It’s not about showcasing the items they possess, it’s about spending their lives doing things instead. 

Or they may be someone who doesn’t care… about anything. They don’t care how they look or what they do. Life is pointless anyway. They drag themselves through it. They throw on whatever is there. What they wear is pointless and so is what they do. The details don’t matter because the larger picture doesn’t matter. Their careless appearance is a reflection.

So basically, you really can’t judge anyone based on their appearance because you don’t know why a person has chosen to look the way they look, but still, how you look still sends out a message. I say, if you don’t enjoy dressing up, don’t do it because it really doesn’t matter what anyone thinks, but try to enjoy some of the details of your life, whatever they may be. Even if it doesn’t matter to the rest of the world, this is your one life, and the experience is all that matters, and the experience is what you make of it and while the way you dress may have nothing to do with the quality of your life, caring has everything to do with living life to the fullest.