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TTM-
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I don't really. But how about vintage Russian watches? They have a certain charm. Guaranteed to make any teenage boy seem interestingly different to teenage girls. But usually handwound.
This seller has very low prices and he only sells NOS. (I haven't bought from him.) https://www.ebay.co.uk/usr/ghrigoriy?_trksid=p2047675.m3561.l2559 For £200 you could buy a pair. Weekdays are often in Russian but it's easy to deduce what they are.
A nifty perpetual calendar function. Easy to bring up to date if you add multiples of 4:
https://www.ebay.co.uk/itm/-/294752936041A 24 hour dial for the Arctic, or rocket scientists, or something:
kjlem
nick_h.
Does he like steampunk? There's a quite a big niche of steampunk watches these days. Whereas the classically retro watches often wander into pipe and slippers land.