Thats a good challenge, but there are shoes out there that will do the job.
New Balance 628 Country Walker
628 Country Walker
For example, you might like the New Balance 628 Country Walker ($80). These are walking shoes built with running-shoe technology. But they have brown nubuck leather uppers with nylon inserts for breathability. They look pretty much like normal casual shoes. Add a pair of khakis and a polo shirt, and you could fit in anywhere.
Another good shoe for rugged walking while maintaining panache is the Timberland Barentsburg Plain Toe Oxford ($100). These have tough leather uppers that have the look and cut of dress shoes, sturdy soles, and a lining to keep out rain. Very nice.
If your travels take you where its fairly cold and wet, then get a pair of Clarks Muckers ($110). These are mid-height shoes for a little more protection, but they will still fit under trouser cuffs. Plus, they have a waterproof lining, leather uppers, and grippy soles. They are good-looking, too.
To any of these, add a pair of SmartWool Ragster socks ($20) for a look thats not too casual but is comfortable for all day on your feet.
The 2008-09 Winter Outside Buyers Guide is on newsstands now. Look for it online soon so you can get prepped for gift-giving seasoneven if everything you pick is for yourself!