There are some nice IWCs in that price range, especially if you like the fleiger / pilot watch look.
Discussion
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. 
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 
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