Without good footwear, walking a long distance can be unpleasant or a complete pain. I have have suffered across the spectrum from poor footwear. In the early days it was mostly because I did not earn much money, most which went on keeping body and soul together.

For my first pilgrimages I wore my usual shoes, a pair of Clarke's with thickish soles with good grips. They leaked, so wet feet was the norm when it rained. 

I was a member of a medieval society. We made all of our own kit, because at that time you couldnt buy anything. It is much easier today. I had made a pair of turn shoes. they were not that good but they sort of fitted. I decided to use them for one of my pilgrimages, walking from home to Peterborough cathedral. If I was lucky, most to the route would be on fields. There shouldn't be much road unless paths were blocked, or just not there. 

I did not have a lot of faith in my home made shoes, so the Clarkes went into my pack, just in case!

In the end, I did not change shoes at all. No blisters either over the whole 45 miles.

I found a man who made replica historic footwear for musuems. He was intrigued by the fact I wanted to walk in his boots, following Chaucer's pilgrims from London to Canterbury. There would be a lot of concrete paths just to get out of London. He suggested a thin piece of 'Thinsulate' on the soles to prevent them being worn out by the hard surface paths that would not have been a problem for Chaucer's pilgrims, who were on horseback anyway.  

The boots were fine. Walking out of London took a whole day. After that I had to make a diversion as the original route was now busy modern roads. 

I used these boots to walk several long routes until they wore out. I even had the soles stuck back on at a shoe shop on the south coast.

The next boots were a modern hybrid. Medieval tops with a modern Commando sole to withstand modern roads. I preferred the previous boots for comfort, but besides modern roads, rocky surfaces had been a problem.

I had two pairs of boots like these over the years. The modern soles were fitted at a different cobblers. I was always asked where I had walked to wear the soles out.

Later I had boots made by Plantagenet Shoes, a maker who measuered my feet for the perfect fit. I later used another supplier and I still wear their boots if the terrain is going to be suitable. 

I still use boots like the ones in the above photo for short walks, but as I am now a pensioner, I do use modern boots for longer distances, especially if there will be a lot of lanes to walk on. Modern boots also have their problems.

 Three years ago I walked around the toe of Cornwall from St Ives to St Michael's Mount. Not a particularly long journey but very rocky. My medieval boots certainly would not have lasted long. My modern boots did not handle the conditions well either. My feet were very badly blistered, nearly raw.

I finished, but the first thing I did when my feet recovered, was to go to a specialist shop to have my boots fitted to my feet. A lot of money and worth every penny.