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it would also depend on the clothes you tend to wear. a cartier santos might be limited to smart casual, business casual, or dressed-up events. it would be hard to match it with very casual clothes like a plain shirt, jeans and sneakers.
a round watch might help in that direction. take for example the pasha seatimer. they offer it in a man's size, i believe 42.5mm in diameter, and can come in rubberized leather or steel. it can adapt to different occasions from casual to business to MAYBE formal.
a rolex submariner is a great and classic choice! lol james bond wore it in the sean connery days!
also depends on what size you are looking for and what can fit you. some guys can't wear more than 40mm (which is typical Rolex sizing), some guys can wear 44-46mm (panerai, omega, jaeger, breitling hublot, ap), some guys can wear up to 48 (corum). these are other brands WHO MIGHT offer something in your range.
the corum admiral's cup, around 46mm iirc was being sold at birks around 5xxx + taxes last i checked. granted, it's not your typical elegant lux watch, but it is very unique and can be much more valuable some day.
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