Digital watches have never been the most fashionable accessory. But I think that will soon change, as display technology has developed in leaps and bounds.
Imagine if your watch contained a screen like the new iPhone, showing an arty clockface that could be touched to reveal more (e.g. date/time, news headlines, weather, your latest calendar appointments).
You could set this all up by registering at a website on your PC and customizing the look and feel - for example, setting the background to be a family photo.
The technology is already all there - touch screen, 3G data, browser displaying HTML / SVG. Finally, the digital watch can overcome its geekiness.