(I guess what I am trying to say is that although this article I wrote might make it seem otherwise, I don't walk around judging people who worry about if their clothes are in style. If asked my opinion of it I would give a negative one, but if my opinion wasn't asked, I typically don't think about it one way or the other. Although in high school I did. And maybe for a few years just outside of high school.)
I think we have all heard someone, when looking back at old photos of themselves say something along the lines of : "What was i thinking? How could I have thought ____(article of clothing) was a good idea?"
What were they thinking? The same thing they are still thinking, "I am scared to appear different from my peers because I worry they will not accept me." Their idea of what is beautiful is based on what others around them see as beautiful.
I do not wish to say people do not genuinely like the clothes they wear, I believe they do, but this sincere liking is derived from what those around them like.
Those who hold most tightly to contemporary fashions, are those most likely to look back with disgust on their own fashions. Think of the ‘hip’ dressers from the 70’s, 80’s and 90’s.
I acknowledge that the clothes we wear make more than a superficial statement about who we are. A person CAN collect clues about another's inner life by observing the clothes their clothing choices. Our clothes signal to the world some elements of our personality and status. When a person wears clothes which are not 'in-style' it can represent a few different things.
One, they are trying but failing to fit in with their peers by dressing like them,
Two, they don't care about dressing like their peers, so are making no effort to.
Three, they want to stand out.
A person wearing clothes outside of contemporary styles can also be a symbol of that person’s desire for peer approval. By choosing to wear clothing which greatly stand out, this may symbolize an uncomfortableness with their natural selves which they are trying to overcome by standing out and being noticed. I think we have all seen people whose clothing seems to say: "Look at me world! I am unique! I am special! Love me!" Of course it could also mean they sincerely love the look and feel of their clothing despite how much they may stand out.
When a person is trying to fin in with their peers by dressing ‘in style’, yet failing, it often represent a certain degree of unawareness or 'not getting it' on the part of the dresser. It is, perhaps, this sense of obliviousness the out-of-style person has which may be responsible for some of the negative feelings their clothes evoke in others.
When a person is capable of, but chooses not to follow trends which set an arbitrary standard of beauty, it shows an admirable level of independence and confidence on their part which is something to be applauded not criticized. We may not even appreciate the clothes, per se, but the motivations behind wearing them is more admirable than that of someone who is unable to decide for themselves what is beautiful.
The point I am trying to make here is that people shouldn't worry so much about whether or not their clothes are 'in style', because the more they focus on it now, the more they will look back on their current clothing choices with regret. The more fitting in with current styles an article of clothing is today, the worse it will look tomorrow. When I look at old photos of myself, I never feel any sense of 'OMG! WHAT WAS I WEARING!" If anything I think, "I wish I still had that sweater, what happened to it anyway? Oh yeah, luke has it."
At the very least, I hope when people look at other's clothing choices they can acknowledge there is no objective goodness or badness about it. It is merely a symbolic expression of a handful attributes the wearer may have and little else. Constantly worrying if your, or others clothing, is in or out of style signifies an inability to think for oneself and the placing unnecessary importance on the approval of one’s peers.