this post was submitted on 24 Nov 2023
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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.
This looks too much like a fake Rolex Explorer 1016 for my taste