Cars, particularly the huge American cars... cool in a way that modern cars aren't even trying to match.
Muscle cars, went hard in straight lines and took a while to stop but what a rush.
SuperBees, Chargers, 442, the 60s brought a lot of muscle.
The Fender Jazz Bass
The Arco Lamp
The Panton Chair
Michael Jackson's nose.
Rickenbacker Guitars as will as Gibsons
The thing about Strats vs Gibsons (and I play both) is that Strats were designed in the 1950's and look modern even today. Gibsons are classics, too, but there's nothing modernistic about them. To me, Rickenbackers have never looked cool, but that's just my attitude.
Chairs by both Le Corbusier and Charlotte Perriand have both stood the test of time excellently in my opinion. Incredible when you think that Corbusier's most famous chair was designed back in the 1920's.
My wife, Susan. Although I confess I am only familiar with the final product, and have little knowledge of the developmental iterations.
Chuck Taylor All-Stars
They are forever cool