Would you pay $5k-20k for a gold-plated version of those shoes?
Regarding Rolex (which I also feel are also overpriced antiques) they at least have a lasting value. They're often heirlooms passed down to children, partners, etc.
A 100 year old watch is awesome. A 200 year old Rolex will be amazing, but possible. But I just can't imagine Apple supporting a first-gen iWatch 50-200 years after release.