There are very few watches out there that can be recognized from more than 5 feet away - maybe a Rolex GMT / Sub (though could be an "homage"), any Panerai, a TAG / Heuer Monaco etc. During the summer here in New York, I wear my shirt-sleeves rolled up with my watch for all to see - and so far, no problems. I'm a bit self-conscious about it if the subway is crowded and I'm holding the pole with my watch right in front of someone's face, but that's very very rare, and only bothers me with the more extroverted, modern LE Speedmasters I own. I'm not worried about my vintage pieces being recognized by the wrong types...
That said, I've been planning a purchase of a Dark Side for some time now, but worry about how noticeable it is on the wrist
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