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 There are some nice IWCs in that price range, especially if you like the fleiger / pilot watch look. 
 Send me pics of which one you like best! I'll look 
 I like the simplicity and readability of this one - it’s big one though (one of the few watch manufacturers that made fleigers during the war). But yes, they don’t hold their value like a Rolex. https://image.nostr.build/6ce0041abc2763d6301e279961c3175a8227012a5934f0ae46a32495f6b8462f.jpg  
 Simple, elegant, classy, timeless 🫡 
 Not gonna lie, they have a big pilot in a brass case with a green dial that is 🔥🔥🔥

I believe it’s called the Spitfire.
However, just like Omega, I suggest searching the preowned market for a discount off retail 
 What do you think of Panerai? Went through a phase of liking them then not liking them 😂 
 Too big for me to consider, personally.
My wrist is only 6.75 and while I have some 40-41mm watches, that’s my limit.

I think it looks great on tanned, muscular guys who wear wife beaters or spend their life boating + diving. 

But in those situations I want to ease into being an old man with a Vacheron 222 https://image.nostr.build/43ab524667ff8444833f5fc5fb1ea21aa5730d00d57c5d016875c23ebc676213.jpg  
 Check out some of their new rotating, bezel models, although the big pilot is definitely their classic 🤌🏽🤌🏽 
 I love their new pilot watches, but they too don’t hold value, better to buy those preowned. 

You also need a big wrist for most of them.

The MK11 is my favorite model of those @ 36mm