RO City of Sails vs. ROO Alinghi Polaris

[Time-After-Time]

Hi,

Long time ago I fell in love with Royal Oak Chrono City of Sails. Had an opportunity to buy an Offshore Alinghi Polaris which seemed like the younger but bigger brother to the COS.
I never really wore the Offshore Polaris much. Found it to be too big and uncomfortable to wear casually and too casual to wear dressy. Sold it to buy a Root Beer.

I've come back to considering the purchase of a RO City of Sails. Am I going to have the same "wrist comfort" and "wearability" issues as I did with the Offshore? I'm usually most comfortable in a Rolex GMT, Daytona or Speedmaster. I don't want to make the same mistake again. But I'm also slightly concerned with a 39.5mm it might wear too small.

Any thoughts would be appreciated.