Citizen Promasters you might be able to grab for that price have some history with the Marina militare
Watches
A community for watch & horology discussion.
Vostok Amphibia. Russian with a watch unique case/gasket construction. Dates back to the 60s and there are hundreds of different designs, the most popular being the scuba dude.
In a movie, too!
f91w was used in terrorism
Most infamous watch in the world, worn by a president of the United States and hipsters, to Osama Bin Laden and AQ/ISIS.
Shanghai 8120: Has China's Standard Movement which was the basis of chinese watchmaking, and Shanghais are highly collected by Chinese watch guys in general
Lorus rm349jx9: Civilian version of a long-time RAF issued quartz chronograph. The original was a Pulsar, a sister brand of Lorus
Vostok Amphibia: Mentioned in another post
If you include homage watches the SteelDive sd1970 captain Willard or the cadisen 62MAS homage or a merkur w10 field watch or a type A or B flieger (like the one from escapement time). You can also ask in r/Chinesewatches to see what other examples they come up with.
The Casio mq24 was worn by the Pope and steeve jobs I think.
Any seiko 5 if you take it as a representative of the whole history of the seiko 5 family but these days it's hard to find one new for under $100.
You can also make yourself an homage to a skx or a 62MAS or a slim turtle or some other watch (usually seiko) you find to be historicaly significant from parts from aliexpress. You can find inspiration on the r/seikomods.