Hi Josie, in answer to your question, if you could find out from him in a clever, subtle way, that would be much better as watches are really about taste and the market is SO big. Having said that, if I were to recommend something (and don't blame me if he doesn't like it!), going by what you say he already has, I would go for something like a Cosmograph Daytona. It's within your budget if you buy pre-owned and a very manly, stylish watch and also different to what he already has but still a Rolex.
I don't know, don't ask me!!!
