Unfortunately I wasn't in the habit of taking screenshots on Win 3.11 or 95 back in the 90s, also because on the Win 3.11 family PC I was only allowed to store files on a single 3.5" floppy disk and images in BMP format were very large, even when storing them with run lenght encoding.

The below is probably one of my earliest screenshots, which attempts to show off my Windows 2000 "Matrix" skin using an Outlook XP new mail window. Nowadays we'd call that dark mode. Given the applications, it would have been 2002 or 2003. I really disliked Windows XP and kept using Windows 2000 for gaming, until some later C&C edition didn't run on it anymore, even after manually copying the XP-versions of the libraries it needed into the game folder.

German speakers might "get" the lame attempt at a joke in the mail when peeking at the "From" field of the mail - yes, back then even professional mail-providers ran mail servers with open-relay configurations or only validated the senders login, but not the from-address.