2. The Cap-Toe Shoe — While oxfords and loafers will never be out, we're sweating the effortlessly cool cap-toe to amp up your autumn dressing game. Wear 'em with jeans and a cashmere sweater for some smooth swagger, or keep the suit-and-tie combo polished. Whether you're going casual or formal, these semi-dress shoes are classic but never stuffy.

Johnston & Murphy Tolbert Cap Toe Shoe, $250, available at Johnston & Murphy; Gucci Marvin Lace-Up, $495, available at Neiman Marcus.