Eleven James Luxury Watch Subscription - $15,108
Buying a watch for a person who has everything can be incredibly difficult, but Randy Brandoff, founder of Eleven James, has reinvented the process. He created a membership-based service that allows customers to "rent" luxury watches before buying them. The most exclusive plan is the Virtuoso Collection, which includes six watches per year — a new one every two months — for $15,108.