Yep, I definitely intentionally trained my fashion sense this way (but mostly online—irl is slightly better but it’s way easier to pull up many examples of a given type on the internet)
This sounds annoying if you treat it as a chore, but I was doing it as a hobby and it was a lot of fun/somewhat addictive
The timescale depends on who you ask but they have definitely been gradually going out of fashion for a while. The kids these days see them as centrally millennial.