I don't think it's about an extreme difficulty with choosing clothing. I think daily life's improvements happen in between the lines; series of small decisions we can make that have a larger effect on us when taken together. It's about freeing up space little by little as opposed to monumental changes (which are much more challenging to implement and maintain).
I started doing this with socks. I bought a package of black crew socks and packed away all of my other socks. It simplified a little bit of my life, and I never unpacked the other socks. I eventually bought in for the rest of my wardrobe. It's nice not needing to stop and think "does this go together?" (or the equivalent of my wife saying "you can't go out looking like that!")
Personally, I don't have problems to choose clothes to wear in the morning, but I don't like deciding what clothes to buy (there's always someone to criticize). It's tempting to buy several versions of the same item, but people around you may think you're dirty because you wear the same thing everyday.
Obama also has commented on his choice to have only one kind of suit. I have a few friends who do the same. Not saying that it makes you Obama or Steve but it isn't uncommon to optimize that part of life away once you have a suitable outfit that looks good.
That is funny actually because people made a big deal about it, so when you are the president and have people paying attention to what you wear that gives you another reason to just stick to one good choice.
My source was this article, maybe Obama doesn't always follow his own advice:
https://www.fastcompany.com/3026265/work-smart/always-wear-t...
It depends on how much making decisions annoy you. For me, it's a great annoyance, not just in regards to what to wear, but what to eat, what brand to buy, etc. So I devise methods to limit my choices or eliminate it altogether. With clothes it's easy — have multiple copies of the same shirt. Similarly with food, I just order daily specials.
I like making decisions, generally speaking. I also recognize that each comes with a cognitive cost and if I streamline some of the minor ones, I'll have more energy each day.
I'm not sure this is how the author is thinking about it. It's probably more like "I'll only have a few pieces of clothing, so I need to make sure they all match."
Are there really people who are so wracked with indecision about their sartorial choices that they'd rather just... not make any?
(The whole Steve Jobs single outfit thing was obviously just an affectation.)