First you have to think outside the box. Very few people dare to do that, because they taught themselves that they are not specialists in styling them and then throw away the authority which they have upon their looks to others who they believe can do a better job just because they are wearing the title of a stylist. Style starts with you, so regardless of who may think that you should wear this or that, you have an imprint of thinking about yourself that designs your wardrobe as well.
I came across a few bitter ladies who invested huge amounts of money both for styling advice as much as for clothing just so a few hours or days later to go back at their old selves.