$69, at L.L. Bean
While it's long been the rain boot of choice for preppy Ivy Leaguers, the L.L. Bean rubber moc is really an all-weather shoe. From cool, damp mornings and occasional showers to full-on mud puddles and snow storms, these babies will keep your feet dry and protected. By themselves, they look a bit strange but the design—pioneered a century ago and still sewn by hand in Maine—has a certain masculine, throwback charm when paired with jeans, khakis or cords. Made from full-grain leather, supported by a steel shank and grounded with the brand's signature rubber chain-tread sole, they're virtually indestructible and can be worn practically every day of the year, with bare feet or the thickest of wool socks. The real question is what color is for you? Brown is an American icon. Preps swear by the blue—good luck finding them on eBay. And the black-on-black was just released for L.L. Bean's centennial anniversary in 2012.