It is such a difficult and ridiculous question. And it's probably been asked before on our forum. But if you're like me, your answer probably changes on a daily or weekly basis. IWC has made so many great watches and still continues to do so today. According to my records I've owned more than 80 IWCs in the past 20 years. I will admit due to chronic regrets, I've owned the same model on several occasions, several times.
Ok, enough banter, here's my favs:
Vintage (Pre-1990) The Jumbo Ingenieur Ref: 1832, designed by Gerald Genta and featuring the upgraded 8541ES movement. It was introduced in 1980 and immediately flopped! Less than 350 pieces were made. Everyone was going quartz crazy at that time.

Neo-Vintage: 1990-2005) the first Cousteau Divers watch. Ref: 3548-06 Nothing horologically special, an IWC gussied-up ETA movement, but this has been go-to watch, in any situation (travel, pool, hot day, or boredom) for more than 10 years.

Modern: I have to with the Kurt Klaus Perpetual Chrono DaVinci Ref: 3762 since it is such a unique complication and amazing casework:

Now I'm leaving out so many of my favorites: Wempe Spitfire Perpetual, the Split Minute Aquatimer, any platinum Big Pilot, the Jubilee Portuguesers, the original Portuguesers (325 and 74) and the military Ingenieurs. Oops I forgot the Mark XI and Mark XIIs, and the new Mark 18s.
Could name 1 or 2 favorites?
Have fun,
Larry

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