Christopher Ward has some beautiful watches in this size range. I also agree with Sinn and Hamilton, Tissot as well as Longines should have some nice selections as well.
Watches
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Seiko cocktail time
It's $1k each or combined?
good question. $1k CAD each. edited post
Okay for your dad it's a bit tricky since it sounds like he's just not interested in watches. Try Citizen NB1060, Mido Multifort Patrimony, something with an eye catching dial that can be suited up
For her dad Nivada Grenchen, Maen Brooklyn, or Lorier Falcon
Nivada Grenchen is being recommended by everyone and seems like a solid choice. Thanks for the rec.
Tbh, anything from Lorier. I think all of their models meet your criteria. Plus, I believe they offer caseback engravings if you want a personal touch
Brew/Baltic/Halios are all great choices. Hearing those, I assume you've got CAD$1000 for each guy...you might also look at the Nivada Grenchen Super Antarctique:
https://nivadagrenchenofficial.com/collections/super-antarctic
38mm, so exactly within your dimensions. Dressy enough to wear for a wedding, but clearly in the "explorer" style of watches (so makes sense for your future FIL as an outdoorsy guy).
Apart from that, might be worth going to a Tissot AD and checking out some of the mid-sized models from the classic dress lines (Le Locle, Chemin de Tourelles). My boss (a distinguished dad type guy in his 60s) wears a black dial Tissot Le Locle and it looks fucking great.
If CAD$1000 is your total budget (split between two guys), you could search for discounts on Explorer-style Seikos like the SPB243, which have a similar vibe to the Nivada Grenchen mentioned above (but slightly cheaper). The Cocktail Times (as suggested already) are really nice, but wear significantly larger than the requested dimensions.
Another side note—does Kuoe (a Japanese microbrand) already advertise heavily to you? If not, they might be worth having on your radar, as they produce smaller classically-styled watches for under $500. Another microbrand worth looking at is Sternglass, a German company that makes ultra-affordable minimalist watches in the style of Junghans.
Here's a vote for the Nivada. As a dad myself I'd be over the Moon if I received one of these.
This looks too much like a fake Rolex Explorer 1016 for my taste
Citizen nb1060 or the nb1050 (more casual). Good everyday classic design and a very welcomed scratch resistant coating on the case that will keep the watch like new for much longer. Also that blue dial in the 1060 is pretty amazing.