We asked Tim Little, the shoe designer and creative director for the 140-year-old British brand Grenson, for the five shoes every man should have in his closet. "It's a bit like choosing my five favorite songs," says the cobbler. He, of course, recommends buying quality but offers up an old army saying to back it up: "Always spend good money on your shoes and your bed, because if you're not in one you're in the other."