One thing to add in response to Demeis' question (and in defence of his mother) - how dark was the nailhead suit? I have a grey nailhead that is a very dark grey with the nailhead being black. I think only a VERY dark brown shoe (say Burnt Oak from Edward Green) would be appropriate with that suit. Several posters have mentioned tone matching, and with brown shoes that becomes an art. I have a number of mid-brown shoes that I wouldn't consider wearing with navy, but some very dark brown and cordovan colors complement it beautifully. I think that a mid to light brown shoe (even lighter than the suit) can work with a mid-grey to light grey, but beyond that you need to get very dark very quick.