Retro, vaguely windows-95-looking linux distro that's actually usable and people like it?

You're confusing themes with entire distros.

This is what you want: https://github.com/grassmunk/Chicago95

I haven’t used the Chicago theme, but if you’re in KDE, the Reactionary Plus theme is spot on and works great.

https://www.pling.com/p/2138468/

Or

https://www.opencode.net/phob1an/reactionary

Chicago95 XFCE on Debian is my daily driver. Having been a Windows 2000 fanboy, it makes me feel right at home.

The Raleigh GTK theme ported to GTK 3 on XFCE is also a quick and dirty way to get a 90s-esque look: https://github.com/thesquash/gtk-theme-raleigh

For an entire distro, there's Hot Dog Linux: https://github.com/arthurchoung/HOTDOG

I don’t think it’s what you’re looking for but what your post reminds me of is ReactOS, though that’s more of a rewrite of actual Windows than a Linux distro.

https://github.com/rozniak/xfce-winxp-tc

There's ReactOS, which is not Linux either and targets the early 2000s Windows versions. Though it doesn't just look like Windows, it's made to be compatible and capable of running those old Windows apps

https://reactos.org/what-is-reactos/

There's also Haiku which has the old Windows look, but prettier imo. It's not Linux, it's based on BeOS, and it's still in beta so not fully usable yet, but it's a pretty cool project

https://www.haiku-os.org/about/

Edit: okay none of those are actually Linux distros so it doesn't really answers the op 😅

Trinity Desktop Environment is really cool - a bit more XP-era, mid-2000s style, though.

Are you thinking of Plan 9?

This is one that was shared recently:

!https://lemmy.dbzer0.com/post/42247576

zorin has a windows like interface. I don't think it necessarily is tracking windows 95 but really the windows like thing is really just a start menu with submenus like windows that I think have not changed much between windows 95 and now.

I think it might be LXQT?

You need to theme it but depending on how you theme it you can get it looking like Win95. In fact I distinctly remember seeing Win95 themes for LXQT

https://github.com/pixelocdguy/windows-classic

I've been using Debian MATE. It's mostly ok.

It's worth checking out Blue95, which was originally made as a novelty but has all the power of uBlue behind it, as an opinionated, batteries-included Linux based on Fedora.

Vanilla? XFCE was looked a bit like Win 95/98 the last time I used it, say 5 to 10 years ago. I’ve been using KDE which reminds me more of XP or Vista in default configuration. Probably why I like KDE so much.

What your probably looking for though is a theme.

Also are the Rolling Stones involved? Asking for a friend.

Maybe Windowmaker?