Thank you for this. I am with you on three out of your four points.
The place where we part company has to do with your statement about the need to wear "fashionable, smart, and stylish outfits."
My emphasis on my wardrobe has to do with comfort and utility, rather than stylishness. If a garment label says it needs to be dry cleaned, I don't buy it. My probably only exceptions are my navy blazer, which dates back more than 50 years, and my sole black suit, puchased for $100 more than a decade ago in a men's shop in Cairo. If anyone cares about the width of the lapels, they can just walk on by.
I grew up post Depression and World War II. The emphasis was to wear clothing that is clean and not torn. That feeling as stayed with me since then.
Look at the many extremely rich people who could buy whatever they want to wear, but have kept their wardrobe simple, like a uniform. (Thinking about icons such as Steve Jobs and Mark Zuckerberg.)
I will leave you with two quotations, both of which are from Coco Chanel:
"I don't care what you think about me. I don't think about you at all."
"Dress shabbily and they remember the dress; dress impeccably and they remember the woman."