So, assuming you have the fundamentals right, ie: no fashion watches, quartz (except a very few), the options of great watches that tell stories are endless. Luckily, there don’t have all to be bank breakers and they don’t have to the ones everyone is after. In fact, do some research and you will find that almost every brand on the spectrum has a couple of watches within their portfolio that’s just a blast, or a blast as is.
Whether you want to go on a hunt for a Rolex Pepsi, or your budget is much more Limited to Mid-tier, you can have so much fun hunting great pieces. Not only do you have not to be boring, but your future watch can be a talking Piece.
Let’s take a few examples: Panerai for example is a Swiss Made, Italian Brand, that goes back to the mid-century working with the Italian Navy and hence the use of the crown guard lock and excellent Luminescence for divers. Starting from a base Pam000 and going up to the Pam687 with its magnificent dial there is a lot to be said. Now Dive watches, at least for, represent the most "Fun Form Factor" out there. From cases, to colors, to re-issues, the sea is big and aplenty. You can settle for the Rolex Submariner, or you can consider the Tudor Blackbay / Pelagos, or for less money and more fun, look into a Jaeger LeCoultre Master Compressor. Want even less and more fun, you have got the Oris Divers re-issues, the Seiko Blue Lagoons and Monsters to satisfy your appetite.
Want amazing value for money Chronos well you are in luck as well. You can go with the tried and tested Speedmaster, or you can explore other fun watches such as the Chopard Mille Miglia (Yes, Chopard is as much a watchmaker as a jeweler with great pieces in its Portfolio, with its LUC Chopard producing High horology Pieces. Want to scale that down a bit, look into a neat Breitling Navitimer, which are great pre-owned value.
That applies to every single Form Factor. There is so much fun and storytelling in watches across all spectrums. Open your mind, do your homework, read up, and always buy a talking piece.