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9k. IWC Portugieser chrono. He loves it. Sometimes I wish he liked it less so he wouldn't wear it as often (worried about a lot of wear and tear).
Join the luxury watch bowl. It's honestly the best bowl on fishbowl IMO. There's a master list of watch recommendations across price points pinned at the top.
FYI Rolex is pretty much impossible to get so I wouldn't even waste energy there. Also had horrible experience with IWC boutique itself and people in the watch bowl will tell you to go to an authorized dealer.
Chief
I would recommend joining the watch bowl! Everyone there would be super happy to give recommendations based on what he likes/has already and price point.
I got my husband a shinola - he isn’t a big watch guy, but he really liked the shinola brand story and would never spend 500-1000 on a watch for himself. The one I got him had a gold plated face which pairs really nicely with his gold band.
Rising Star
I got him a 13k rolex. I knew he always wanted this model / color combo.
Chief
About $4k, Nomos
Got him a Cartier Santos for 7k. He loves it, got the last one in store.
$5k panerai. He wears it constantly and loves it.