re: If not a Rolex, then what?

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IWC Portuguese

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One of the best looking watches there is to look at in a watch box, but the thickness and lack of a bezel make it wear like a sports watch, but look is definitely more than casual. I had one I bought new in 2011 when retail discount was around 20%. I shopped it on trades for a while because I rarely wore it and it took about 2.5 years to find a buyer that gave me a suitable price for it. I've had several IWC's (still have one - an early 2000's Flieger UTC), and one thing you can count on is them not holding value very well.

The point is if your taste changes and you don't keep every watch you ever buy, despite all the negative on here about Rolex - that's a great bet, especially SS sports models, the problem is these can be hard to get access to. I would recommend the 39 mm Explorer 1 (214270). Ticks a lot of boxes and comes in at 7500 USD. Prior to this March, the 116710LN (Black Ceramic Bezel GMT Master II) would have been a nice choice at 8450 USD - it is now discontinued and the new versions of the Pepsi (BLRO) and Batman (BLNR) on the Jubilees are around 800-900 more, but exceedingly difficult to come by without a relationship at an AD. Both SS versions of the Submariner are always a great bet if you can get your hands on one at retail.

With regards to used, any 5 digit model Expl II, either Sub or GMT Master II are also good choices, coming in at 5.5-9.5K+. I actually prefer the 5-digit models to the newer 6-digit ones with the super case/maxi dials.

One quick thing about the Tudor Black Bay Heritage I've heard mentioned in this thread- the 41 mm model is quite thick. the polished case sides look huge. Gilt accents on the matte dial are excellent, but the Black Bay 58 fits more in line with the DNA of that watch (Nod to Big Crown Submariner 6538) at 39 mm and less blocky in stature.