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Originally Posted by LoganSnake
You're taking it a bit out of the context.
As long as the watch is stylish, you will make a favorable impression on those who care. Those who care are more than you think. My boss is one of them. He is a watch fanatic and has a couple of watches that cost in excess of $200,000. To him, a good watch means having a sense of style.
So while the Fossil you linked to might look good on a kid or on the beach, something like this Tissot Le Locle will automatically upscale you in the eyes of many people.
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Well, it's not so much out of context as hyperbole, exaggeration for effect. My point was that I felt Will was being irresponsible by not qualifying his statement that anyone who does not wear a watch appears poor. I like Will, and I know he can take a bit of critique.