Mine was probably when I relapsed towards religion at age 15-16 and joined my mom's conservative megachurch, naïvely thinking I can convince them to be less bigoted and more "christ-like" as well as accept science
I wore over the top outfits. Suit jackets, headbands, waistcoats, bright red skinny jeans, leather biker jackets, fedoras, big glasses with fake lenses, studded belts, etc etc in all sorts of combos.
The fedora and waistcoat over a white dress shirt as casualwear is what I'm most ashamed of. I don't know what in the hell I was thinking. I must have looked like a total dickhead around my normally dressed peers.
This was a phase that probably lasted no more than a year when I was about 18-19. I wish someone had told me that I looked ridiculous lmao
I love it. Don't be ashamed, you were telling the world you were open to trying new things and being adventurous. Finding your own style rather than following the mainstream is sexy. I used to be that way and slowly confirmed and now I'm trying to get back to my younger self, where I cared less about what others thought.