Jaeger LeCoultre Reverso

Known simply as “The Reverso”, Jaeger LeCoultre’s iconic square dress watch has changed very little since its debut in 1931. It hasn’t had to. The Art Deco inspiration behind its aesthetic is timeless, and its party piece, a razor-thin flippable face, is nothing short of ingenious. Some models can be optioned with a second dial on the underside, a clear caseback, or a protective rear (like the original). Explaining its raison d’etre to those who catch you playing with it at the bar should serve to keep conversations going well into your third Manhattan — and if that doesn’t work, tell ’em Don Draper wore one.
Expect to pay: $5000