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Soul-
You can't go wrong with the Sub, it's just as you get older it's a sporting look that still suits any occasion but is just a little less an older mans watch.
The other thing with the older subs is they look great when they have a little wear, slight softening of the case and bezel. I think the normal bezel watches can show their age a bit, especially a stretched bracelet.
One thing about the sub I couldn't get my head around when I first got it, from new the bezel had really clear machining marks on the fluting. It just seems really at odds with the perfectly finished case and attention to detail everywhere else. They're still there but worn a little from 10 years of use.
Airhead
Even then I would say, only if you need a sports watch. The explorer/air king/datejust is a watch for life. The sub gets less suitable the older you get!
A friend has a deep sea because he always has to have statement watch. It's just not my thing but it suits him.
Went for lunch a few months ago and 5 of us were wearing subs, 3 guys, 2 girls, all different models. No one brought it up, thankfully. I'm not a huge fan of the supercase/ceramic Rolex models, I have the GMT but prefer the sub most of the time.