Right now my two watches I wear the most that fit this price would be the Monta Noble , and my Ball Engineer Marvellight, the Ball I have on a grey sheepskin leather. The Montas bracelet is extremely comfortable.
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Teddy Baldasarre made a great video abt this question on his YouTube channel. Would recommend checking it out. His followers voted on a tournament of 32 watches and the Oris Big Crown Day-Date won against the Longines Spirit in the final. Some disagreed but oris makes an excellent watch
Christopher ward c60 trident pro 300 or c63. Looks great everywhere, extremely well built, and you can fast swap the bracelets/straps for multiple different looks with the same watch.
I’ve been wearing one daily for a year and it still makes me happy.
You might take a look at some of the Sinn 556 versions, I really like them.
The new longines conquest would get my vote. Versatile enough for most occasions, 100m WR and solid movement.
Sinn 104 all day
Look at the Casio Oceanus line.
Ultimate GADA watches.
Depends on the style you want obviously as there are a bunch of good options at that price point especially if you go used but my personal choices would be sinn or a seiko mm300
Sinn 556 MOP.
Nomos Club Campus
Squale Sub-39 Vintage GMT.
Oris Diver 65. (Ask AD for a discount).
Seiko Alpinist.
I put down the Squale and Oris because they are a vintage-style watch. They dress up with a leather strap, much like a Tudor Black Bay 58.
Since its not a diver category.
I say:
Seiko Alpinist, if possible get the sarb017
Speedmaster Reduced is also pretty cool IMO
Hamilton Khaki Murph is nice looking too
I think at this price u can get the basic grand seiko with spring drive
Orient Bambino. Incredible value at approx $250 CAD but the quality makes it worth much more. I have two of them and I really enjoy them