Every American visitor we ever hosted here in Europe has underestimated the amount of walking. No kidding - not a single exception.

They had read about it in guidebooks, but somehow none of them could imagine that the structure of European cities is different from the structure of, say, Los Angeles and that visiting European cities means walking, walking, walking and climbing stairs.

Who is fussing about style? He should wear whatever he wants - as European teenagers do. I have a 17-year old at home, he wears jeans, trainers, t-shirts. When going out I make him wear a shirt with a collar or polo shirt, which he thinks is waaaay overdressed.

But as everyone says; have comfortable shoes. Doesn't matter what they look like. I think Americans often don't walk a lot. Certainly not all day on cobblestones.
Bring well worn-in sports shoes. Boots are not comfortable on uneven paving.

Oh and jeans with 'ridiculous holes in them' are all the rage, but more for girls than boys.

There are no such thing as an 'ugly tourist (american or whatever) but europeans in average definitely dress differently. At every age.

Being European, I strongly believe we dress better but ...

My daughter dresses with ridiculous jeans full of holes (...) and some years ago they were all buying 'en masse' converse sneakers. And Superdry and Abercrombie and Fitch...

I'd let him bring what he wants to bring, including the cowboy boots. It wouldn't be the end of the world if he has to give in and buy some sneakers while on his trip, and then the capitulation to comfort would be all his :-)

(I'd try to talk him into bringing a spare pair of comfy shoes, but que sera, sera.)

No one dresses worse than British bachelorettes out on a stag night....

BigRuss, I haven't see any Europeans fussing about style. We don't care what anyone wears, we are too busy getting on with our own lives to even notice most of the time.

or better said....hen party :)

Why should tourists have to look just like locals? The cowboy boots will set him apart in a good way - I always wear what I wear at home when traveling in Europe and that is also pretty much like Europeans wear - especially teens everywhere in Europe and much of the world all wear basically the same 'cool' things.

The comfy shoes for walking however is a valid point.

This must be an oldest child. By the time we got to the third child going to Europe he could have worn rose petals for all we cared.

Thanks for all the advice.
I will try to get it through his head the amount of walking he is going to have to do and that the heels on his boots will be a problem on cobblestones.
I am not sure why he has such a thing for cowboy boots he has been that way since he was a kid.

Good luck!

When I was 21, I traipsed all around cold, rainy Venice in soaking wet canvas tennies that I dried on the ceramic stove in my pensione every night. Why I brought those shoes I can't even say, but I had the time of my life :-)

I wasn't able to talk my son out of wearing his cowboy boots on the trip to Europe. I hope his feet don't get too sore but perhaps he will learn a lesson.
He did give in and get a couple new shirts.

He can buy other shoes if the boots become an issue.

I was just about to mention that here in Europe, even in the UK, we have shops, but crefloors got there first.

I went to Rome with a group of 17 year olds a few years ago and I was surprised at how much time the boys wanted to spend in shops. They were just as bad as the girls for wanting to shop instead of looking at the sights.

Well he came home still wearing his cowboy boots so I guess they didn't hurt his feet enough to buy shoes in Europe.
He had a good time so that is what is important.

Oh I'm late to this party, I was coming to say he should wear what he wears at home. If he's comfortable walking all day in his cowboy boots, that would work. And I was right!

that's good news, JAW.

Has he said what [if anything] he liked about Europe?

Good to know, thanks for the update, JAW. I'm another who would love to hear what a teenage boy liked and disliked about Europe!

I has talked a lot about London, Paris and Rome. I haven't heard him mention a place that he didn't like.
I think he was a little worried because he had never been on a big trip like that before so I am glad things turned out well.
He did say that he had never walked so much in his life, LOL
I reminded him that I told him that would be the case and offered to buy him walking shoes. He said his boots were fine and that he didn't get blisters like some of the others did.