I think probably a lot of self selection. I would guess most people get involved with open source so because the technical problems being solved are interesting. I would guess the people who choose to work on emacs don’t necessarily care about web design. I think most open source web frameworks have pretty decent design!

I personally think it's an aesthetic choice at this point. I actually kind of like it.

I've come to associate the borderline absurdity of logos for open source projects with projects I like at this point, and I do think these kinds of logos are almost a shibboleth for certain kinds of software. I'd say it's less about not knowing how to do "better" or driving away designers and more about signaling "hey, this is NOT corporate software." I've always considered it as a community thing and a cultural quirk more than anything else. To come in and say "this unicorn is ugly, let me fix that for you" would be to misunderstand a lot of things about the context that the software exists in IMO.

What's wrong with it? I use org-mode, and I find this site readable and useful?