Typically, I'd vote race cars uncool/seriously uncool. But cars from this era transcend the race/road car argument.
From an engineering perspective, they are typically developed from road cars (or were the basis for future road cars), and the differences between the versions are very narrow.
From an aesthetic perspective, there are a number of cars from this period that are simply the pinnacle of design.
Even if you know nothing about it's race history (3 Le Mans 24H victories, including taking 5 of the top 6 places in '57), or it's innovative design (aluminium monocoque, innovative aerodynamics) or its iconic 3.8l straight 6 (which sounds utterly gorgeous), the D-Type is just achingly beautiful. The lines, the stance, the way the rear wheels sit in the arches, the wheel design... it's just perfect.