Mido has some great selections. Models over 1k but you can find sales that get them under your budget.
Watches
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I’ll echo the other poster who said take them shopping. That way they get what they want, plus they get the experience, which will be just as, if not more, memorable than the watch itself.
This is the best! I took my son shopping with a $200 budget.
I can't even imagine what they would do with $1000.
I bet it would include, a Casio Duro, a Seiko Cocktail Time, a Seiko JDM Chronograph, storage, straps, bracelets, tools and more.
Certina new / second-hand would be a good option for a younger one.
Yeah - good calll.
Something from the DS PH range if they've got the wrist (have you seen the new DS PH1000m release btw? Especially the LE).
Very, very well built divers for the money from this brand.
If you don't have the wrist for something from the DS PH range you can do a lot worse than the Action Diver - particularly in Ti.
Mido Ocean Star GMT. It can be found for less than $900.
https://www.midowatches.com/en/ocean-star-gmt-m0266291105101.html
If new then Traska, Baltic, and Farer. I’m your older son’s age and have a similar collection and I’m eyeing a Farer as my next piece. The fun designs and color ways means it’s not meant to directly “compete” with some of the more expensive pieces he owns. If they’re into fliegers could also check out Stowa and Laco these are very cool and the brands have cool histories.
If used you could find some Nomos or Monta watches in that range.
why pass them an “airport watch”
This collection is well under $1000.
You could throw in 3 more icons: a square G-Shock, a Casio Royale, F-91W and still have money left over for a nice meal together.
38mm Hamilton Murph.
You could find an Oris Big Crown in the $950-1100 range on Jomashop or Bob's. Would make a nice daily for your older son, to go along with his more "special occasion watches."
For the younger one, I like the Hamilton kfa suggestion, as well as the Murph.
Note the size ranges for each of these.
Take a look at Christopher Ward as well.
Sinn 556
Something cool and fun. I've been digging the Citizen Tsuyosas. They could each pick a different color, and you could get one too, all for around $1k. Tissot PRX is another one.
You can get some great deals on used watches that would normally be closer 2000. I’d look for a used Sinn 104 or 556, or maybe a oris aquis or big crown. There’s plenty of other good choices but I’d definitely look on the used market especially on watchexchange.
Don't buy watch guys 'a surprise'; let them choose.
I think this is an opportunity to obtain a very special watch in terms of sentimentality ... bought with money from an uncle who's a watch guy and facilitated by your father - it's got all the ingredients to be 𝘵𝘩𝘢𝘵 watch.
I'm not sure that you can beat a re-issued Seiko diver from the ProSpex range in terms of sentimentality. We all love a (relatively) inexpensive rugged watch, for Weekends, holidays and general wear - especially when young. Buying pricier watches from premium brands is often a milestone marker; they become special for a different reason. I like the idea of taking the opportunity to make your unremarkable watch remarkable via sentimentality.
I reckon there's a watch for both of them - the same watch, for all 3 of you even.
My choice would be one of the 62MAS reissues in the ProsSpex range. ☻
Who got his watches? Maybe you could use the money to buy his actual watches for your boys?
This is just below your budget, and is one of my favorites, dont know if it suits your sons.
Orient Bambino is a good start. Can be worn dressy or casual and is really good value for an automatic ($250 CAD). Or for a good casual option, Hamilton Khaki Field (Approx $600-$800 CAD)