A good leather shoe has to be a bit snug when first worn. If leather shoes are comfortable from day one, chances are you will be able to throw them off your feet once they are broken in.
The breaking in process can be done in several ways.
One way is wearing the shoes at home for short periods of time. You can wear them while doing the dishes, making the beds, or any activity that keeps you on your feet.
As you grow more confident, you can wear the shoes on short outside ventures. A quick trip to the store, or picking up the little one from school.
If despite your best effort the shoes stay snug, dont despair, you have options. Wear the shoes with a pair of thin cotton socks. The extra volume on the foot will stretch the leather.
Another way of stretching the leather is filling the shoe with water and wearing them wet. Not only will the coolness of the water sooth your aching feet, the water will cause the leather to grow suppler. By wearing the wet shoe, the leather will literally shape itself around your feet.
I learned this trick first hand when I visited a company and found a large puddle of water near the front entrance blocking my way. I could either take off my shoes and wade through the water in my stockings, a get my shoes wet. I opted for the latter. Once inside I had no option but to keep my shoes on and let them dry on my feet. To my utter surprise, once my shoes were dry, they were super comfortable.
You could also try to manipulate the leather by stretching it between your index fingers and thumbs. This should not be done carefully, with velvet fingers so to speak, but rough and with strength.
If the heel of the shoe is the problem, do the same. Pull the leather between index fingers and thumbs and alternate by pushing the leather of the heel downwards towards the sole of the shoe.
A potato can also be of service. Simply peel the potato and stuff him in the shoe. The juices of the potato will soften the leather.
Large pieces of newspaper rolled into balls and stuffed inside the shoe have the same effect on leather. It makes the leather suppler. Careful with white shoes though, the black ink of the newspaper might cause stains.
Remember that new shoes should never be worn without stockings. Feet swell in shoes, due to friction. By wearing stockings friction is eliminated.
You might also want to keep a Band-Aid handy for just in case.