I don't think proper watches (if cared for) will ever lose money.Before you go out and get that watch be sure to do your however as only a handful of watches can be deemed as investment worthy.
It's a mad cult following that drives demand, so it's not easy to guess the next rising model.
Plus the fakes out there... They are getting really close to the real thing... Even (especially) in vintage watches.
That said this Covid situation will stir up demand and supply a bit....so a rare piece might pop up more frequently.
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Those awful, gauche things worn by footballers, Russians, rappers and oil money types will come and go. A Patek Philippe will always be a good bet though.