A lot of professionals just use the most favorable looking pic they can fimd, even if it's not the most up to date. But you're right, my guess is it was probably Kip a long time ago. I showed the dentist bio pic to a non-runner friend and he thought it was a woman
From what I've heard and read about Kip, he spends a lot of time biking and was formerly a big tennis player (not sure he still plays as much though but it might explain his tanned face), and I imagine he has very white teeth because he's a dentist, and maybe his hairdo has changed over the years from looking kinda like that Wendy's fastfood restaurant girl to male pattern baldness with a bandana in races? Not sure. Or maybe he got into motorcycles and loves the bandana look now