In 2006, Eddie Montgomery of Montgomery Gentry showed up at the Kentucky Derby wearing a jacket almost as loud as his band's most rowdy rockers. That's his now ex-wife in the photo above. Only at the Derby can someone get away with wearing roses and polka dots (or are those rhinestones?) in 2006. The Kentucky native has been a frequent Derby reveler, but in recent years he's toned it down some. Black isn't a color many of the high-rollers choose to cheer for the horses, but they pulled it off six years ago.