[DJ2020]

You could break it down to Sport watches and dress watches just to keep it simple. Submariner and GMT for sport or DJ for more of a dress look.

Maybe spot one in a advertainment or one in public or find a excused to pop in a AD for something else and point one out. Say something like (If I were to pick one, I sorta like this one) and check his response.

You can pick up on what he likes. I'm sure he would be happy no matter what you choose. A watch is personal item. Every one and there brother has a sub or two or Five. Careful not to follow herd enthusiasm unless he truly wants the same thing as millions of other people.

Do your best to find out what HE wants. Again, If it's a gift from you, I'm sure he will cherish it. Also don't forget there are MANY fine brands out there!