I've got tricky hair to deal with (tons of cowlicks), though I'm very lucky at my age I still have a full head of hair. Anyways I am not the most trendy person, and I have one haircutter I go to at a high end salon, a middle aged Italian-American lady (I only trust middle aged women with my hair actually, nobody else can get it right). And I just let her do 'whatever looks good', it usually comes out fine.