After finishing another busy (exhausting) term in Cambridge and returning home for the holidays, I found myself (obliged by my mother) rummaging through boxes full of nostalgic junk. I sat on the floor of my room and scoured endless piles of photos, diary entries and letters from long-lost friends. An interesting pile I stumbled across contained the annual class photos of my 12 years of schooling. I went to a school with a very relaxed dress code, and therefore found the class photos to be a great medium through which to see people’s personal style evolution, without exterior rules dictating their stylistic choices.

Speaking of stylistic choices, mine were not as timeless as I thought they were. When rediscovering old photos, we tend to assiduously regret the fashion choices that were made by our past selves. It’s easy to pick apart colour combinations, judge how unflattering a shirt is, and despair at a hairstyle.

“Why should I expect to be satisfied with outfits I was assembling 5 years ago?”

I wanted to do the same thing with the stack of class photos I found. But this time I paused. Picking apart my outfits that I put together at the ripe age of 13 is frankly meaningless. It might be the perfectionist in me, but why should I expect to be satisfied with outfits I was assembling 5 years ago? I was only starting to understand (and I am still learning) what makes a good outfit, the trend cycle was at a completely different stage, and social media was not yet brimming with endless fashion content.

But were the outfits that I consider fashion blunders really all that meaningful? Not really. I can’t remember if I was particularly proud of them, but I must have liked them and found them decent enough to wear them to a class photo.

I think that regretting the outfits you wore is an important and perhaps eternal stage in one’s “fashion” life, if you will. Especially with the rise of social media, it seems as though any dimension of style experimentation leading to an imperfect outfit can tarnish the polished image that we are all trying to keep.

But isn’t fashion all about expressing yourself, and, crucially, feeling good about yourself? In this quest of finding your style it’s inevitable that some of the outfits that we will wear will not make the history books; but instead of cringing at them, we should embrace how far we’ve come.

“Our biggest enemy in making fashion fun, personal and exciting is, sadly, ourselves”

Being able to embrace “getting your outfits wrong” doesn’t come naturally, and isn't a particularly pleasant process. To some extent, it’s rejecting what you know works well together and diving into the deep unknown. When I have an outfit that I’m not completely sure will work, I try to wear it on a day when I have no definite plans with anyone. It just so happens that with people who I have known for quite some time, it’s harder to try something new. In my mind, their perception of me implicitly dictates the outfit that I choose to wear.

I don’t believe that you find your style and stick with it forever. What it means to 'be fashionable' and the image you want to portray changes at different stages of your life. A way I try to experiment is by noticing which clothing items create a strong reaction, even more so if it’s a negative one. Is my dislike fuelled by me finding the item unfashionable, or because I think that it’s too much or too different for me? If the reason is the latter, this shows a fear of experimenting, which it is imperative to overcome as it not only applies to fashion, but can also permeate other aspects of your life.

Accepting that you are going to regret some outfits is necessary, and dwelling on them is useless. On the contrary, we should marvel at the change that has been and will be seen in our fashion styles. Our biggest enemy in making fashion fun, personal and exciting is, sadly, ourselves, but the fear of making and regretting our mistakes should not stop us from experimenting. Getting it wrong is an art that needs to be mastered.

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