Looking for something not too old ladyish that I can walk around comfortably in and won’t get too soaked if it rains - thanks everyone !
On two Scotland trips, for all occasions, I wore knee-high leather fashion boots with a fairly flat heel (about 1" or 3/4"). I sprayed them thoroughly with silicone waterproofing before I left home.
These are the kind of fashion boots I can tuck your jeans into in the daytime, the better to avoid wet jeans legs since the raincoat only comes down to my knees. In the evening, same boots but with tights and a dress. I even wore these to play mini golf at St. Andrews Himalayas. You'll see young Scottish women wearing boots all the time.
On those rare days when the weather was dry or I knew I would be indoors the whole time, I switched to a pair of ankle boots (shooties, booties, whatever you want to call them).
I always bring a little pair of slippers to give my feet a break in the hotel. Fold-up slippers I bought some years ago from Footsmart take up about as much packing space as a deck of cards and they're extremely sturdy, surprisingly cushioned despite the thin sole.
If you want to be spotted from a mile away as an American tourist, wear a pair of hiker-joggers. Especially in city areas, these may not look old-ladyish but they're a clear departure from local taste in footwear.
There’s already a post about this topic from a few months ago.
I think it depends if you are walking around on flat ground vs. trying to get up any of the hills/hikes where you might get muddy. If you're just in the city, Clarks, Borns, Eccos, Joseph Seibel, Tevas all have sneaker-like lace up shoes that aren't bright white but have comfortable soles and most of them have water resistant options. You just have to try a bunch on and then you'll just "know" what feels great on your foot. And honestly, Europeans wear sneakers all the time -- it's a myth that it's only the Americans that wear them. And trust me, people will know you're a tourist from your clothes, behavior, visiting tourist sites, and your accent, so I would focus more on what makes you comfortable rather than how people might look at you. If you're walking around a lot (we average 8 miles per day), your feet will appreciate comfort over style (but extra bonus if you're somehow able to find both -- I never can).
I've found that the Merrell Moab line of hiking shoes are very comfortable and long lasting, especially with Dr. Scholl's half length inserts for heel support and comfort. I've worn them on my last two trips to Scotland, and have found them to be excellent for city walking, low level hiking, and rock scrambling. They come in wide widths, which I need, and also are available in waterproof (they claim) and breathable styles. They are definitely not old ladyish! My wife wears them as well.
BTW, for some reason, Chuck Taylor Converse sneakers, both high top and low top, seem to be the favorite of teenage girls all over Scotland. Don't know why.
I have found the Keen shoes to do a great job of fitting the bill for an active walking adventure. I wear the men's Austin shoes. They are rugged, have enough stiffness to hold up on uneven paths, are fairly waterproof with a little work on the upper, and look good enough to wear in a decent (though not dressy) restaurant. I have found them to be quite comfortable to wear too.