ManMyoDaw

It's tricky to pick a watch by nationality, because many of them come from multiple places. Do you mean designed in Italy, or manufactured in Italy, or a company owned by Italians? All of these things exist, but rarely at the same time.

Many Italian-owned companies manufacture their watches elsewhere. By the same turn, there are some foreign-owned companies who use Italian factories to make watches. For example, Panerai watches are owned by a company in Florence but mostly made in Switzerland; Squale watches are owned by an Italian business family, but also made in Switzerland.

Watches that are both designed and made in Italy tend to be ultra utilitarian (but high design), like Unimatic (Japanese movements but assembled in Italy) and Panerai (see above), or extremely high-end stuff like Locman and Bulgari. None of those three companies really make standard dress watches that you could wear to a normal business meeting.

You might have luck with Visconti's "opera" line, if you can swing the $1000 price tag:

https://www.visconti.it/en/watch-opera/

Also check out this article:

https://teddybaldassarre.com/en-int/blogs/watches/italian-watches

If you have a rugged/outdoorsy lifestyle, explore G-Shock! Loads of YouTube videos about which ones to loo for, but the DW5600 and 5610 are classics.

If you have a more stylish/buttoned-up aesthetic, check out the Orient Bambino 38mm options. Beautiful watches, amazing price, great brand to get into for a first watch.

If you want to get weird, look at Vostok and Raketa--both are ex-Soviet brands that make interesting (sometimes loud) watches for very little money.

Then there's the vast universe of microbrands and Chinese watches, which I know nothing about (they've emerged more recently, and each are a whole "scene"). Each have their own subreddits and experts.

You can't really go wrong with any of these. My slight preference is for the Le Locle, especially the one with the black guilloche dial on a shiny steel bracelet. Chemin des Tourelles would be my #2, but it's a little less refined-looking to me.

The Classic Dream Swissmatic is also a fine choice, but the movements (the internal organs of the watch) of the other two are much better. They'll last for 80 hours on a single wind, whereas the Classic Dream will be about 50% of that.

All of these are watches made in the many hundreds of thousands, so they will be extremely easy (and relatively cheap) to maintain and repair over the coming years. Congrats to your dad!

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.

Most I've already spent is circa $600 USD (I have a Hamilton and a Tissot in addition to several cheaper ones), but I'd be willing to spend around $3000 for a Nomos or Longines (can't do it right now because have to prioritize stuff like home renovation and car maintenance...maybe in a year or two I'll hook up a new watch)

Hell yeah—the proportions are incredible. Looks great on your wrist. Somehow it looks way better than some of the earlier "Marks" I tried. Do you have the bracelet too?

How do you like that piece?

https://preview.redd.it/e9ya7nxjf72c1.png?width=3024&format=png&auto=webp&s=c72ab7ea19dc5144a58b23920d325482c206789d

I'm wearing your watch's younger sibling, while my son furiously cheers for the Seahawks

Ballsy and admirable choice for a first mechanical watch. Phenomenal choice tbh