My boss refuses to take any of recommendations for improving the companies out dated website because "our age market is 50-60" it has to be blan and simple.

Like seriously what the fuck, this is why no other generation is staying in the webpage more then 30 seconds!

I've dealt with the same. Just because it's an older demographic, doesnt mean they are blind... Though do need to err on the side of clear rather than clever interfaces

Actually I think your boss might be right here. New layout might scare loyal visitors.

Depends a lot on the site though and what it is meant to showcase and what the changes are.

But there's a big risk that someone will no longer find the content/button they need "that was always there" and then stop using site next time that happens.