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Is a pilot watch like a Stowa Airman acceptable in a formal workplace, or is it out of place?
Unless it was a very specific or strict workplace there is no reason why a pilots watch cannot be worn. Whether it looks good on the wearer's wrist is another question; a 55mm pilot on a 7 inch wrist is not going to look great.
how will you fit it under your cuff?
I've seen folks, including partners in big law firms, in bespoke shoes, bespoke suits, and huge digital Casio G-shocks or other such watches.
Agree. As I pointed above as well, it's been the trend with top level management for a couple years now. I think it's meant to say "I'm a down to earth guy" or something