Here we see another black velvet kippah, this one from the 18th Century.  So the modern-style kippah doesn't seem so much "modern" as "regional."  Although it doesn't surprise me that this ended up being the predominant style in America two hundred years later; this is where most American Jews came from.

Here he's wearing a very Russian-style hat.  I don't know if there's a black velvet kippah underneath.

He also wore a modern-looking black velvet kippah.

Interestingly, the oldest picture of a 19th Century Russian rabbi shows a very simple, modern-looking black velvet kippah. I was calling this "modern" when I saw an Uzbeki rabbi wearing it (see above), but maybe this was a regional thing instead.

Also moved to Jerusalem.  He wore a large black kippah that seems much more modern.

Moved to Israel and helped found the Haredi community in Jerusalem.  He wore a Haredi hat.  So, we're already starting to see something that's recognizeably modern.

Also moved to Israel.  I don't know whether that turban is more Iraqi or Israeli. 

Also moved to Israel.  He wore . . . I can't really tell.  It's a large black head covering.  Maybe a turban?

Moved to Israel and adopted the local head covering: still a turban.

Moved to Damascus and then Israel.  He wore a Turkish head covering.