fashion in taipei

I've been exploring Taipei with my cousin this trip, and one of the things that we try to do in our conversations is guess where someone is from. I seem to clearly stand out like an American. Today, on a hiking trail, a woman's water bottle was rolling away from her but towards me. I picked and handed it to her and she paused briefly before responding with a curt and accented, "Thank you!" Even without putting too much thought into how I dress, others can tell with a quick glance that at the very least, I'm not from Taipei.

My cousin has more experience with looking into different types of fashion and admits that he has embraced a Japanese and Bay-Area mix of fashion. He quickly is able to determine certain groups of people -- "They are definitely from Japan, you can tell by the hair and the tops they wear."

To be honest, I've never put much thought into how people dress or keenly looked for it in the streets of Chicago (maybe because everyone is looking straight down to avoid the wind on their face). On one hand, I'm interested -- it's a way of presenting who you are to someone. I wonder what type of style I would choose.

But I also wonder is it something even worth pursuing. Lots of time and money would be used to invest in clothes -- would that be better invested in something else? I fear the fixation on individualism is not healthy one.

For the record, I think  I'd go for a more skater/cali style. Not sure how that flies by at work though.