I'm fortunate. I have a couple of watches that I love, like my Sinn 104, that no street thug would ever pay any attention to. I really don't feel like I'm making a compromise when I wear them. If I know I'm going to be somewhere that could be the least bit sketchy, I just wear those. For me, it's like any other watch selection I make in the morning - swimming? diver. Physical activity/working on the house? beater. Dinner out? dress watch. Unknown? Sinn.
I have lived in the city for many years. Crime is high here. I feel like I've got some pretty good street smarts. Situational awareness goes a long way to avoiding being a victim.
Sadly I have a box full of them and probably 20% get regular wrist time. It's just so easy to buy them when they are $15 to $35, but it starts to add up. I don't even want to know how much that box of failed experiments has cost me.
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