Strage reaction here. I'd assume that the thought of dressing the same every day has at least crossed most people's minds on HN. It's an engineer's (lazy man's?) solution to a common problem. For me that problem has more to do with clothes management and what to do when your favorite outfit isn't available than with the paradox of choice.
As for what to wear, if you're in a startup you should wear your logo as much as possible; asshole or not.
Pro tip for people who have trouble finding matching socks in the morning:
1. Donate all your socks to charity
2. Buy a single pair of socks you really like many times
Yep. I've been more or less this for years, although I have a white set and a dark (black or navy blue) set.
As soon as the current set starts to show wear (holes, ripping out when putting them on), I demote all the socks in that set to cleaning rags and buy a dozen or so new pairs, all exactly alike.
I don't think it's especially wasteful -- assuming the socks are chosen at random they should all be about equally worn, and I do recycle the old ones for cleaning, shoe polishing, and so on. They're actually great for that, especially if you turn them inside out so the rough texture is on the outside.
Threw the old socks away, but I have about a dozen pair of tan socks (all the same), a dozen pair of the same style in dark brown and half a dozen of black dress socks. I have zero desire to be stylish in the sock department, so this greatly simplifies my life.
As for what to wear, if you're in a startup you should wear your logo as much as possible; asshole or not.
Pro tip for people who have trouble finding matching socks in the morning:
1. Donate all your socks to charity
2. Buy a single pair of socks you really like many times