Running games and old software on smartwatches is nothing new. We have covered these hacks a lot in the past. Hacking Jules has shared a video that shows Windows Me running on an Android Wear watch. It was installed with Bochs emulator on a LG G Watch.
As you can tell, Windows Me was not designed to run on smartwatches like these, so this is probably not worth trying. To be honest, not too many people miss Windows Me anyway.