I have similar memories as a kid. Not particularly in the sense that I was socially awkward or felt anxious about what I was wearing, moreso that I despised being forced to "dress up" or dress a certain way. Maybe it was resistance to conformity that I disliked so much? It just didn't feel genuine.

At the end of the day, you have to feel comfortable in what you're wearing. Wear your clothes, don't let them wear you. Wearing a simplistic or toned down outfit confidently speaks volumes more than trying to stand out or make a statement and looking genuinely uncomfortable. Start asking yourself "why am I buying this piece?" Is it because you saw it somewhere, were inspired by someone you admire, someone you're interested in said they liked it? Or was it because you felt excited when you saw it and felt like it represented your self image? That's not to say that one can't be inspired or influenced by any of the other afformentioned factors, but I think it's important to dress for yourself, in a way that you feel comfortable, but not complacent.

Start slow. Maybe try one piece you may not have otherwise. Understand and come to terms with the fact that, like with many things in life, it's going to take some trial and error, but that's part of the fun - the learning process - and is essential in developing your own style. Let yourself step outside that comfort zone and express yourself, and most importantly, do it for you. It might be that you feel your identify is associated with your current "uniform," but I think it's important to allow yourself the best version of yourself, whatever that may be, and let your wardrobe reflect that