Matthew McConaughey wears a TAG Heuer Monaco

Benjamin Barry is an advertising executive who bets his colleagues he can make any woman fall in love with him in ten days. Matthew McConaughey plays him in Donald Petrie's How to Lose a Guy in 10 Days (2003) with the easy confidence of a man who has never had to work for attention. The premise only holds if Ben is charming enough to make the bet plausible, and McConaughey was built for the part.

On his wrist is a TAG Heuer Monaco, the steel square-cased chronograph with a blue dial that TAG reissued in 1998 after years out of production. The square case settles it; almost no other watch wears that shape. It is a watch bought for its look more than its movement, which is the kind of thing an advertising man understands by instinct.