If this photo looks like what is behind a pretty hedge row on a road in Ireland you are wrong. It is the street in Temple Bar, Dublin. All over Europe, you will find that you will not likely be walking on newly poured concrete. Cobblestones have been there for generations and will likely be there for many more. Please wear sensible shoes. You will thank me for this.
You are going to be doing a lot of walking on your trip. The people you will meet will not judge you by your footwear unless it is ridiculous or a pair of brand new white tennis shoes (known as trainers in the UK). Be comfortable and wear shoes that are broken in.
I have a great pair of black walking shoes that have gone thousands of miles. They polish up nicely, but they do not appear new - because they aren't.
I am sure you will see some women in high heels in Rome, but they are only going a short distance. I am also sure that you will be tempted to wear flip-flops or open-toed sandals. This is not a good idea. Think practical. Take socks which are always useful and I pack a pair of slippers (IKEA $2) that take little room, fold to the size of an envelope and do not weigh much. Slippers are always a good idea.
Now if you are from Texas and are determined to wear your custom made cowboy boots, take a large package of moleskin. Moleskin is always a good idea too.
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