1. Oris Divers Sixty-Five
I love this watch so much I couldn’t care which one landed on my wrist. The purist in me calls for the black-dialed reproduction of the original, but the blue dial is too handsome to ignore. Great watch, great price, so my benefactor doesn’t suffer.

2. Parmigiani Fleurier Bugatti Type 370
A radical watch bearing the name of a car marque I have worshipped since childhood? No brainer. It deals with two of my loves, and the movement is astounding.

3. Harry Winston Opus 14
My other love is music and this watch thinks it’s a jukebox. Another no-brainer, especially since this is redolent of 1950s American diners. Wildest function imaginable— interchangeable dials and functions.

4. Junghans Meister Pilot
Despite my qualms about anything German of a militaristic mien, this watch was born during peacetime. It is a perfectly styled, functional chronograph, and I adore those finger-grip bezels. Underpriced, too.

5. Panerai Mare Nostrum
This recent reissue is now out of production, but I’m sure there are some kicking around. I need a sister for my pre-Richemont Mare Nostrum. Coolest-looking chronograph ever.

6. Jaeger-LeCoultre Grande Reverso Ultra Thin
Every once in a while, I pretend that I am a refined gentleman. As I already own a Patek Philippe Calatrava, this—with red, blue or brown dial —would be my alternate choice for those sober moments.

7. De Bethune DB29 MaxiChrono
De Bethune is, for my money, the best watchmaker on the market. I adore chronographs, and this is their best chronograph—every box is, therefore, ticked. Gorgeous, intelligent, useful— I’m in love.

8. Rolex DeepSea Challenge
OK, so James Cameron will never let go of his 51mm DeepSea Challenge, so this might be a silly choice. In which case, a regular DeepSea will do nicely. The ultimate diving watch? Who cares? I don’t even swim.