That always struck me as lame. If someone that well off wants to eliminate that decision, then just have a professional clothes person create clothing matches. 'A' goes with 'A'. 'B' goes with 'B'.
What it really is, is someone making a statement about how important their decisions are.
Lots of well off people still wear interesting clothing.
It sounds like more of an ASD symptom. Having routines and being unable to break them. I have mild ASD and often wear the same clothes/copies of the same stupid free startup tshirt for no real reason other than subconsciously I hate change. I also really haven't bought new clothes for years due to it being too much change to handle. I do make sure they are clean when I wear them tho!
I wear a collared shirt and black pants to work every day, but the shirts are different colours. Frankly, my fashion sense isn't great but I look decent in a nice collated shirt and my wife does have a great sense of style (heck, she makes a dork like me look good, I'm always in awe of this ability - it's like a superpower!) so this makes complete sense to me.
I think these people apply the same principle to many other decision making processes in their lives, not just picking clothes, which is very visible hence everyone talks about. I guess saving on clothes is small but many little things add up quickly.
That's bullshit. Wearing the same outfit added some mystic to Steve Jobs. It may not work on the public persona of every CEO but it obviously did for Jobs.
What it really is, is someone making a statement about how important their decisions are.
Lots of well off people still wear interesting clothing.