What are the best shoes you've ever had?
Mine are what I call my 'multi-purpose shoes', and they are my one fashion item that makes me a target for insults from both my family and friends.
I like them because they are comfortable and they neither add nor take from whatever outfit I wear. This means I can wear them with pretty much any outfit without drawing too much attention to them.
The funny thing is, it wasn't until I pointed them out that I started to receive insults and pressure to wear other shoes. That is because they are inconspicuous ;)
My advice is this:
Fashion is subjective and beauty in the eye of the beholder. You are free to express yourself and be who you want to be. So long as you are not hurting anyone, wear the shoes that make you feel like you!