Jesus sailed; therefor a Rolex would not be out of line. I have a GMT stainless steel watch that keeps time to the minute; all the FAA requires of pilots. Handy when I fly in different time zones. Jesus knew some rich folks, in today's world they could afford to give one as a gift.
The reaction of the healed-and-saved to Jesus was often of copious gratitude. A wealthy man might be moved to bestow, not just a Rolex, but all his jewelry on Jesus. Now, what would Jesus do with it? Whatever He did, it would be to glorify the Father.