When I read your post, this is what I hear: you think the people you used as examples are losers. You’ve stated multiple times that you don’t think that makes them bad people, and I believe you, but you think LESS of them than others. For reasons that may or may not be of their own choice, they have become losers. Hence your concern about other people’s perceptions (if you are doing similar things to those people, then will other people view you as a loser?), and your continuing insistence that you’re not judging them (your post about recognizing people who are “dialed down”). My advice:
Re-evaluate your mindset regarding success. Financial success is only one form of success. You can be successful emotionally, spiritually, socially, civically, philanthropically, familialy(did I just make up a word?), etc. Spend some time reading about spiritual and emotional growth. Maybe you will come to the same conclusions you have now, maybe you will not. Maybe you will decide that someone who “could be doing much better but chooses to do less and make up the difference by stuffing newspapers in his shoes” is merely prioritizing a different form of success than financial. Maybe this will make you less concerned about your own frugal choices that might seem “dialed down”.
Re-evaluate how you present yourself to the world and when you present certain aspects of yourself. The thing about the obviously well worn tie really jumped out at me. I can’t think of many circumstances where it would be appropriate to wear a tie that is worn out. A tie is part of a professional wardrobe; wearing worn out clothes is not professional. If you are in a situation that calls for professional attire, it is not a frugal choice to wear clothes or accessories that are obviously worn out. Such a choice can negatively affect your ability to effectively network or grow your career. I work in a professional environment where I’m required to wear a suit and tie. If I show up at a meeting or event wearing a suit that has holes or stains, or a tie where the threads are wearing at the edges, it will be noticed and will negatively affect my future career and income prospects. Your posts give me the impression that you are aware of this and it is affecting your self confidence. That doesn’t mean you have to go out and replace your whole wardrobe with brand new Gucci suits, but it does mean that if something is no longer functional, then discard or donate it and replace it. There is a fantastic post in the “Best posts you saw” thread about someone who really upped their wardrobe and the huge boost it had to their confidence, to the point that other people noticed and pointed it out to him AND his co-workers. Think of the positive impact that had not only on his mental state and his ability to interact with his coworkers, but on his effectiveness at his job.