I feel the same way about washing dishes. I care about having clean dishes but I really don't like washing dishes. Even now with a dishwasher, I get annoyed having to hand-wash the dishes that aren't dishwasher-safe.
In my case it's jeans and a t-shirt, clean jeans are piled next to clean t-shirts, I work my way down both piles until there is one of each then I put the entire laundy basket through the wash and re-pile them.
Unless it's a special event or a meeting I really don't care, jeans and a t-shirt is fine for day to day wear and one t-shirt is much the same as another.
Clothing choices are a pretty big stressor for my SO and by extension me.
What it really is, is someone making a statement about how important their decisions are.
Lots of well off people still wear interesting clothing.
http://gawker.com/5848754/steve-jobs-on-why-he-wore-turtlene...
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.
I still get to make a decision about which color shirt I'm going to wear that day, but don't need to think about even reaching for socks, since they're already in the shirt roll.
(admittedly the outfit choosing part was only about 5 of those minutes, but still a good chunk of time over 5 years)
edit: oh yeah, I don't even choose a color. I just line them up ROYGBV.
Recommended. I have a "uniform" that I wear[1][2] that works very well for me across different weather, places and events. I established it about ten years ago and have reaped quite a return from that initial investment.
Now, in addition to my default "uniform" I also have codified what I wear the rest of the time into 2-3 different other[3] "uniforms" that are better optimized for a few different situations. I hope to get at least 10 years out of these investments.
[1] Jeans, Next Level poly/cotton vintage t-shirt, long sleeved patagonia capilene 2 (black). Running shoes.
[2] Since I have at least 10 of each item, I always have something clean to wear.
[3] Casual warm, casual cold, manual labor.