What kind of women’s boots should I buy for maximum style, comfort, and to get the most bang for my buck?

I need to buy a pair of pretty basic black boots for everyday wear that can be dressed up or down. I would wear them with skirts and dresses mostly, but also with jeans. I’d probably want them to be mid-calf with a small heel or no heel. I want them to become a staple in my wardrobe so I’m willing to spend a little more money if necessary (probably up to $400), and I don’t want anything too trendy that will go out of style right away.

Does anyone have any recommendations of a good brand of women’s boots that have offered comfort and style and also stood up to the test of time? If I’m going to shell out the cash I don’t want them to wear out after one season of wear! Thanks!