Don't Overthink Your Underwear

I haven’t changed my underwear to go on a ride in ten years, and I’ve never, even once, been three-quarters of the way through a ride and thought, “Son-of-a-whatever, why did I have to wear this underwear? What was I thinking?” But I’ve often gotten home and stripped down to find cotton boxers, and thought, “Hmmm. These are supposed to be lousy. How come they weren’t?”
When I think a little about it and can as easily grab one kind or another, I like thin wool seamless underwear, but mainly because I can ride it in all weather and not change it after the ride, because it doesn’t clam up. Then I can flip it inside out the next day and use it again. The day after that, another flip. Wool is three-ride underwear.
But cotton underwear is not going to kill you or wreck your crotch. Life on a bicycle is rarely like life in the snowy mountains. Most of the time, the challenge is a fair-weather ride of half an hour to two and a half hours, and nothing bad can happen on a ride like that.
I’ll go out on a limb and say that any ride that requires, or actually genuinely benefits from  a padded, anatomical, high-tech, microbial synthetic chamois slathered in crotch cream is a ride I don’t want to do. Wearing shorts like that on a non-epic ride works—people do it, people like it, and no harm’s done; but it’s kind of a weird-looking, expensive overkill.

Socks are not performance wear.
High socks look kind of funny, but if you don’t care, nobody else should, either. By the time you’re an adult you know not to wear thin cotton socks in cold or wet weather. The same kinds of socks you’d wear for a hike will work fine. Underthink your socks, if that’s possible. Bike-specific socks work great, but they’re just neck-and-neck with any other kind.