Hey there
Celebs pull this off with a permanent hair stylist and loads of guts. They also use weaves so they can chop and change their looks as they please. For you skin type (which sounds rather rich), I would say go for a few highlights and then keep adding colour until you have reached a shade that is both comfortable for you as well as okay for your hair. Do not make the mistake of doing a rash colour that ends up damaging your hair and forces you to go and tint your hair in a darker shade to try and get it to look healthy again. Start off small and work your way up.