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Honestly, I don’t think enough people would know what a pilots watch is. Depends what model though - if it’s blue face with tons of complications then probably not. If it’s a spitfire I’d wear the shit out of that. Any simple and classic watch isn’t too much (I also have an IWC). Leaning on the side of just wear it bro who cares.

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Wear it. Don't ask people what watch they're wearing just so they ask you back and then you flex it's an IWC. Just wear it and don't be flashy about it or turn your wrist to check the time (everyone has a phone now). If there are people who genuinely like watches & in IB there are a ton, someone will notice and ask you and then you can have a conversation about it. I also don't think the watch you are mentioning is particularly flashy or overboard; (some) people get high school graduation presents like that.  

 
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