During the cold months, when it's not wet and sloppy or extremely cold I spend most of my time in Caterpillar work boots that I've had for years. They are neither insulated nor waterproof, but they are comfortable for walking and their thicker soles and ankle coverage help keep my feet from getting cold.
But every once in a while we get a week in January like the one we've just had, where it's above 40 every day and sometimes hits 50, and I don't always feel like wearing my boots. Back in the spring I got these shoes from L.L. Bean, and they have turned out to be the best walking shoes I have owned.
They are meant to look like the old-school hiking shoes that have recently come back into fashion, but functionally they are more of a general-purpose shoe. They're a bit funny-looking, but not nearly as bad as the puffy "mall-walking shoes" you tend to see older folks wearing. (I'm not ready to give in to those yet.) I also like that they are quite plain, devoid of unnecessary detailing.
Although I kind of like the tan, I went with the gray, which is more low-key. The blue laces are anything but subtle, but fortunately they came with a second pair of laces in matching gray. The blue pull tabs on the back aren't so noticeable, so I don't mind those. They aren't available in wide, which I tend to find more comfortable, but these are wide enough that it's not an issue.
I've had some foot issues over the years, including a cramp/nerve-pinch thing in my right foot that tends to manifest after I have been walking or standing for a while. It doesn't matter what shoes I am wearing, so whenever I wear new shoes during a day of walking I expect the cramp to show up. But with these shoes, no cramp. I have no idea why, but I think it may have something to do with the footbeds. When I first put them on they tend to feel a bit strange, but as soon as I start walking everything feels fine.
Bean happens to be offering 10% off all orders through next Wednesday (1/22), and these shoes are already marked down $10 from their original price, so you could get them for $63.