$1000

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If the person is a fan of “military” watches I would probably go for CWC



If simple and elegant is the way, I could live with one of the many Stowa’s available for under 1000. This for example:
 
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Nice watch suggestions.

Bulova Lunar Pilot is about 800 but little under 500 on sale now

 
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I’m gonna throw a dressy yet sporty curve … Timex Galli : $500.
 
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Ok, we have $1,000 to play with and that gets you these two watches:

1) Tissot Powermatic 80 Green Dial $775 MSRP (but can be discounted)


2) Merkur Panda Chrono (Seagull movement) ~$200


The Tissot for a rugged and stylish daily-wearer and the panda chronograph for some fun on the weekends.

(photos from Google search, credit to the original photographers)
 
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Wow, I really have enjoyed this thread! Thanks for many watches to now go look at! 😀
 
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I really like that Doxa in orange.
For my relative, I’d suggest a Seiko 5 with GMT @ $475.


I came here to suggest the humble Seiko 5. I've bought several variants lately, and they are all really fun.

And non-watch nerds seem to like them. I've gotten more compliments about Seiko 5s in the last couple months than the rest of my collection has garnered in 5+ years.

Edited:
 
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I thought this looks good and well within budget

 
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Since the SM300 is still one of my favorite watches, I'd suggest the Helson Sharkmaster. ETA powered and priced at $729.00 USD. I'd probably spend a little extra and replace the bracelet with a US or Forstner 1450 to get rid of the clunky clasp it comes with and still be well under $1k.