On 22 February 1996, Swiss ESA Astronaut Claude Nicollier was launched skyward onboard Space Shuttle Columbia STS-75 with a prototype Omega X-33 strapped to his wrist. Over the next couple of years these evolved into the space fight qualified X-33 Speedmaster and became an essential tool watch for space explorers. A quarter of a century and two iterations later it still is, there will be several on orbit right now.
These four are a bit closer to home.
Claude Nicollier, aboard STS-75
24 March 2008, STS-123 crew onboard the International Space Station posing for some in-space portraits, all wearing X-33 Speedmasters.
The first prototypes of the X-33 were actually branded as flightmaster and featured a Seamaster style bracelet.