I purchased my first watch (Speedmaster, 3rd from the left) exactly 10 years ago in October of 2016.

Acquisition Order:

Speedmaster -> OP 39 -> RO 15400 (Gift) -> Pepsi -> 5320G -> DayDate (Gift) -> Reverso

All are in pretty good shape except the speedy which is in desperate need of a service. They basically all get regular wear except the Speedy and the OP.

Each watch has a special meaning/event associated with it, and while I admit it's not the most interesting collection, I am pretty happy with and find it diverse enough for basically anything.

i.imgur.com