Kind of a tough question. I started buying skate brands like Zoo York and lots of polo in high school. After that I was trying to find a pair of Ian Brown (of the Stone Roses) x Adidas shelltoes. From there I found Sufu and Niketalk and got heavily into sneakers: SBs, Air Maxes, Air Forces mainly.
Started copping streetwear like stussy and supreme. From there got a pair of Nudies (LOL no idea where those are), APCs and a few pairs from the artisanal denim brands. I sold off alot of my sneakers used that money to start copping designer pieces. Early on I had cloak , robert geller, lad musican things along those lines. From there got into some weirder more expensive things like Rick Owens and Raf.
So probably started heavily following high fashion in about 2005-06. Right when the golden age I mentioned before was happening. I bought and sold a lot of stuff online and it was really through that I started exploring and developing a solid wardrobe. Made alot of mistakes , bought Ann D stuff that never fit. Realized I wasn’t skinny even for dior homme to look amazing.
I’m at a point where I’m super comfortable and hardly make buying mistakes because I know what will fit me and work with my personal style/wardrobe. I’ve almost come full circle because outside of a few grail items, I’m just rotating stuff through, adding a few basics here and there and mainly just experimenting with styling and brand mixing.
I get more enjoyment out of creating content than buying things at this point in my life.