There is no better figure to start a story about affordable watches with than Steve Jobs and his watch, both of which followed the Think Different approach. Because in the world of the celebrity watch—where a Rolex Submariner worth thousands and thousands of dollars can seem austere—there is no better counterprogramming than a super-affordable timepiece. Billionaire CEOs like Jobs are actually no stranger to practical cheap watches. And the rest of the figures on this list all come at affordable pieces for seemingly different reasons. Tyler, the Creator squeezes joy out of confounding people, John Mayer is an equal opportunity collector, and Barack Obama’s watch might convince the public he is a guy anyone could grab a beer, and then maybe go shopping, with. Also

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