When you live as an out trans person, clothing takes on less importance than ever (I think) because your identity has been augmented by the ability to interact and express oneself fully as one desires at all times. Going out to have coffee with a friend or doing groceries must above all consider comfort before anything else. So, I will go out with a black T, jeans and ballet flats and be perfectly happy doing so and I don’t feel drab or frumpy in the least.
Years ago, I worried about blending in but that isn’t a concern for me any longer and what I now desire to wear has changed over time especially since my life is no longer about a series of scattered outings; it is just everyday life. Use of lipstick for example, abandoned due to mask wearing, is now an optional addition I sometimes omit .
It is interesting to measure the change over the years, but in a nutshell, it is that the focus has shifted increasingly from the externals to the internals.