I got my son of the same age and general need Loake 1880s off pediwear.com. If you wear the same shoe every day, it will wear out quickly though. Even if you rotate with another pair, you will need to replace the heel lifts regularly and will need to resole at a decent cobbler once or twice to get 5 years out of them.
Santonis are good. Brooks Brothers Peals are on sale and a good value. Made by Crockett and Jones and Alfred Sargent:http://www.brooksbrothers.com/IWCatSectionView.process?IWAction=Load&Merchant_Id=1&Section_Id=523