Depends on what "old school" means. It's sort of the fashion-forward shoe for 1930s classic style a la Fred Astaire or the Duke of Windsor. They're a bit flashier than balmorals/oxfords with vamp stitched to quarters. Today, I suppose they are old school in most people's minds. They can be very elegant, though they are often made with a medallion on the toe. This floating medallion has often been castigated by SFer manton. I think he is right: a floating medallion, especially on a wholecut, draws too much attention to the medallion and not enough to the shape of the shoe. It's rather like having a shirt with bright-colored wide stripes spaced very far apart. The eye is drawn so much to the stripes that it doesn't see the shirt as a whole. To be safe, I would get a plain toe, non-brogued wholecut like the C&J Alex. In black, they're great for evening social, fine for business formal or funerals.