Dear Diary,
Do we/people dress for other people or ourselves?
This leads to a larger question about ego and ambition, but to keep it simple...
A lot of people dress to look good in front of people, so they choose items they think will look good. Other people don't necessarily think those items look that good though, so why bother? Aren't the chances much the same if you just chose something random within the scope of TRENDS?
TRENDS... are seemingly the result of common (perhaps unconscious in some) agreement on a currently desired look. However, within these trends people still tend to be picky. Why? It can't be because they dress for others, given that the chances of impressing aren't known, and you might as well just pick something random. Why try to be known as that guy that looks cool with the watch? After all, that's just what YOU would think if you saw someone wearing it. Does it mean there's no point?
Or maybe, they dress to please themselves. To impress themselves. Confusingly, I find most people are more impressed with themselves when they realize they're impressing others.