In this case, Jean-Luc chooses both the fantasy-wear and the fantasy for which he wears it.
If I had access to a holodeck I would choose Star Wars, Harry Potter, Leverage (omg! I want to play holo-Leverage!), and of course, Star Trek. These are the series I create fanworks for, and indeed, cosplay and roleplay. And if you look at the characters I am most passionate about portraying, the ones I relate to the most, you may learn something about me. So what does Dixon Hill tell us about Jean-Luc Picard?
Most importantly he’s a detective. Jean-Luc loves to solve mysteries, it’s a part of all his downtime activities and an important facet of his personality, that drives his career in space exploration. And again, Dixon is a street-level hero, the kind Picard most respects; Jean-Luc would be all about The Defenders over The Avengers.
Jean-Luc knows the classics so well he can quote Shakespeare and Melville at the drop of a hat but he chooses to play out serial pulp fiction set in wartime San Francisco. I love it.
The 1940s is one of my favourite eras for fashion and Jean-Luc and friends rock it.
In First Contact we even get a nice nod to Casablanca which is awesome.