My wife and I have met Rick Steeves in Varenna, IT, and he is exactly as appears on television. Tall, friendly, a wealth of knowledge, confident, interested in people, easy going, and easy to speak with.
I agree with the cargo pants comment. Far too many pockets for practical use, and the person wearing stands out as a tourist, most likely from North America. I would suggest when travelling one dress comfortably and casually to a point. The " expedition look " has it's place in other parts of the world, but not in Rome, or Berlin, tropical kit pith helmets included.
There are many restaurants and a few venues here that require a jacket, and possibly even a tie, which is easy to pack. One may never use the tie, but a jacket certainly makes sense when it cools off or rains, which it does in the Summer months.
A jacket or suit does seem to work magic in the airports and with the airlines, especially in Business class, or if hopeful for an upgrade. Again, sans pith helmet.