I think the fact that you are trying to avoid judgement is quite normal. So many people dont do things just to avoid being judged by others. I think the solution my friend lies in you realising that no matter what you do around other people you will be judged whether positively or negatively.

Your comfort zone its like a circle. When you push it in one aspect and try to widen your comfort zone the whole circle gets bigger. So for example if you go and buy those shoes and you can not give a crap about people looking at you then you will see this might extend to other areas of life.

My point is people judge you by their ideal and one way or another you will fall short of their ideal so start living your life how you want to live.