I suppose it depends very much what you want your shoes to be. A good pair of shoes can last for many years. It depends how often you wear them; even the best shoes worn day-in, day-out, every day will be ready for the bin in three or four month time. But if you have a reasonable quantity of shoes, or you wear sneakers most of the time and "real shoes" only every now and then, shoes can last for ten, twenty or more years. Add to this, your feet, unlike your waist, will change very little in the course of your life. The same shoes that fit you today will fit you in twenty years time; if the pants will still fit, has to be seen. So you can either buy high-fashion shoes willing to ditch them in a couple of years time when they are dated or you go for classics that will never date. I suppose that is the more boring route. The choice is yours. But if want to go classic, then you should stay away from all extremes of style. Square toes are a bit last season already. Have you seen the latest Saint Laurent or Miu Miu numbers? Those pointed toes qualify almost for offensive weapon status and in the hollow space you could carry a crack heads weekly supply. I believe the smartest shoes have a chisel toe; it's not round, not pointed and not square but a combination of all three. But it is very much a question of personal preference. One word of warning, if you have a bit of a Charlie Chaplin walk and turn your feet outward (like I do), stay clear of square toed shoes; makes one look like Donald Duck.