Seek the aid of a qualified shoe repair professional to help you decide which kind of oil might be best for your shoes. Olive oil has many adherents, but some report that it leaves oily spots behind and leads to deterioration of the leather.
Consult the sales staff from whom you purchased your leather shoes as to which oil is best for your shoes.
After applying one coat, let it absorb thoroughly into the shoe. Depending on your shoe, you might need to wait several hours or a full day before applying another coat. If you can see your shoes are still oily, or feel greasy to the touch, let them continue to sit until the oil has done its work. After the oil has been absorbed, evaluate the softness of the shoe. If you wish it to be softer, apply another coat in the same manner as the first and evaluate the softness again. Repeat as necessary.
If your shoes have not as soft as you’d like after a single coat, repeat the process again until your shoes are as soft as you want them to be. Sometimes you’ll need to apply several coats to reach the level of softness you want.
If your feet start to hurt while wearing the shoes, take them off and swap them for another pair, even if you haven’t worn them the whole half-day.
Feet are sweaty. If you wear the shoes two days in a row when they’re new, they will not have time to adequately dry out, especially when they are new and still tight around your feet.