When the weather starts cooling off, flat boots will keep you warm, comfortable, and still fashionable. Typically mid calf to knee high, you'll find most in a soft leather or suede. With buckles and zippers they add character to any outfit. For a sleeker look, go with a pull on pair where the focus is the whole boot. Stick with black or tan so you can pair them with any outfit all season long. Flat boots are always great with a pair of geometric tights or worn over skinny jeans. When you're wandering around the city flat boots are an essential.