Any ready-to-wear pair of shoes will be a compromise. In an ideal world, and if money was no object, your shoes would be made to measure. A last, an exact replica of your feet (both feet, as nobody's left and right foot are absolutely identical) would be carved out of wood and your shoes would be made on this last. Even then, a last is no plaster cast. Your measurements will be interpreted to the fashion and custom of the time and the place. A shoemaker in Havana would have a different understanding of what makes a smart shoe, from one in London. Not only different workshops but also different customers have their own concept of "well fitting". Allegedly Hungarian shoemakers aim for the tightest possible fit. Only once you have all those different ideas brought together, you might arrive at a "perfect" fit. In addition your feet vary. They are lager at the end of the day, in high temperatures and after being having been on you feet for a long time. It is best to try on shoes (or have measurements taken) in the afternoon. Do you have problems at always the same spot? To a certain extend shoes can be stretched where needed. You must have shoes that fit you well. Stick not only to this particular make, but also to that particular last. To go to really expensive makes will not improve the fit, it might be, if Lobb or Edward Green or Lattanzi happen to fit you right. But if their last(s) and your feet sing from a different hymn sheet, no way will you be better off. Go to a good shoe shop and have your feet measured. If you think 10Â½ D is right, maybe 11 C or 10 E is better. Â I would only get shoes from eBay if I knew the make very well. And I would certainly avoid any high-fashion shoes, as their lasts will change according to fashion. Currently all YSL, D&G and Gucci shoes are ludicrously narrow and pointed. Next season, who knows, they might be back to squared toes again. If you get a new pair of shoes, don't wear them all day long, particular if you cannot change them (leaving home at 8 a.m. and not returning until 8 p.m.). Start them indoors, then wear them to shop locally, when you know you will be back home two hours later and can take them off if need be. Leather shoes will adjust to your foot to a degree, but that also depends where you expect them to ease. (Not in the length and not in the toe box where the inside toe cap might provide heavy stiffening). This applies particular to loafers, which can easily become too loose fitting, as usually they are also less rigidly constructed than proper lace-ups.