Fashion leather "work boots" or jump boots (e.g. Red Wing, Danner). Oddball, usually lightweight, sneakers. Selvedge jeans with the cuff roll (maybe hipster, maybe tech hipster—need context and other clothing cues to tell the difference). Expensive hiking & bouldering/rock-climbing brands, for shoes, boots, pants, and jackets, especially (meanwhile, normal fans of hiking who aren't doing a lot of very long hikes just wear shit from Costco). Merino wool everything. $100+ hoodies.

Perma-shorts were definitely a thing for sysadmins back in the day, devops kind-of killed them off ...

I just googled based on your comment. I assumed this was just socks with programming jokes written on them, but appearently it is actually a term for knee-high socks https://knowyourmeme.com/memes/programming-socks

I certainly hadn't heard of this either.

I would say they were describing the people. I didn't realize you can't dress in comfortable clothing you like without making some kind of statement about gender roles or whatever.

That's what seems to be implied by the GP, though. The only thing being referenced in connection to that term is how those people were dressed, and that they were "gross".

It’s common to take appearance and dress as an indicator of such beliefs though, however misguided that might be.

That’s the consensus of a vocal minority on the internet today, which is often toxic in its own right.

I was a programmer in the 90s, and no, things were not that simple. Problems, sure, but this kind of black and white revisionism helps no one.