Self-contained scuba helmet - Scuba diving started out with enormous, clunky, and heavy suits which provided oxygen to the wearer via a tube to the surface. Nowadays, most of it is still pretty bulky, but Immersed Senses has changed the game. Their helmet features a display up front to show you via GPS where you are and it extracts oxygen from the sea water to give you a truly self-contained breathing apparatus.
Case in point? Imagine all those wonderful drivers you see each and every day in traffic... flying over your town and even your home.
Next up? People (and their cars) falling from the sky.
#15 - Dick Tracy, cartoon character that first hit print in the 1930s, had a two-way wrist radio/watch.
Image: en.wikipedia.org/wiki/Dick_Tracy#/media/File:Dt2wrr.jpg
Great image series!