If you had to pick just 2…

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May I ask the make of that strap on the Speedy? Beauty
Actually that is a Hodinkee strap from some years back. I don't visit the 'dink anymore so I have no idea if they still sell these....
 
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Fairly standard - but it works well!

Speedy covers off being a dress watch, when needed.
 
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If we cast aside things like sentimental attachment which would play a big part in any future watch culls as I have a few that have attachment of some sort or another now that I will never part with. So getting rid of that for a minute and just choosing my two favourite watches from my collection, these two....