Omega Speedmaster Michael Schumacher

The one and only Omega Speedmaster to ever be endorsed by supermodel Cindy Crawford in 1996 (and, uh, Michael Schumacher, too), this is an exception to our usual rule of anything-but-Rosso-Corsa. The red strap might be a little too too, but otherwise it's a great-looking watch that makes a statement without being gaudy. This one even comes with its original box, a rubberized container meant to look like an F1 tire.