The first successful Apple Watch jailbreak was presented last year at the hacker conference Defcon. Such an attack is anything but easy, as various security features make such an undertaking difficult.
WatchOS 4.1 can now be hacked on the third generation Apple Watch using "jelbrekTime". This jailbreak is an early version, which is why it is primarily intended for developers who want to help adapt the exploit for more Watch devices and software versions.
Not attractive yet
The "advantages" of such a jailbreak would be to have your own watch faces or to design and install your own themes. Smaller system optimizations would also be possible. Jailbreaks for the Apple Watch are currently still in their early stages. The development of complications and more would not be ruled out in the long term. It will be some time before there are really public exploits for the Watch with real features.