Bradley, to be honest, modern cars are all very same-looking and generally uninteresting. 1950 cars look cooler than modern ones. In the specific case of cars, however, I'd imagine there are way too many design decisions dictated by safety requirements. Steering wheels in particular are all ugly, but that's because they're now required to contain an airbag. But that's an okay tradeoff to make — I, for one, enjoy being alive more than anything else.

UIs however? What has changed since 1999? People still use a keyboard and a precise pointing device to interact with their computers. Screens are no longer CRTs and can be bigger and with more densely packed pixels thanks to technological advancements. Yet none of this calls for UI changes. When someone has bought a 27" monitor, they didn't do so to look at all your fonts that are readable across a room, glorious whitespace and unnecessary shadows. They did so to be able to fit more information on the screen. And those touchscreen laptops? No one uses the touchscreen with any kind of seriousness anyway. It's a marketing gimmick. It's definitely not something to redesign your UIs for.