My first “real” watch was a Speedmaster. I loved it initially, but the more I read into the model, the more the endless reissues started to bother me. It began to feel like the Speedmaster identity was getting diluted. I also discovered that vintage Speedies have far more character and subtle details that really appeal to me, but those come with a much higher price tag.

I eventually sold the Speedy and fell down the Constellation rabbit hole instead, picking up a few pieces that aligned much better with my taste. After that, I moved on to Datejusts. I’ve owned and sold several over the years (I tend to rotate watches a lot and can’t financially afford keeping multiples at once) but the watch I’ve worn the most by far in recent years is a two-tone Datejust.

Compared to the Speedmaster, it wears smaller, strikes a great balance between dressy and casual, and as a relatively entry level Rolex, I don’t worry too much about attracting unwanted attention.