I've been updating my Pinterest board where I'm collecting images of older men in fashion advertising.
Why do I do that? Because they're a rare sight and we need to persuade the myopic menswear industry that they'll get access to a large and very affluent customer demographic if they advertise to men over 40. Men of that age group can lose confidence as they see high street shops selling largely to younger men. A little encouragement, in the form of advertising acknowledging that a) older men exist, and b) they can be stylish too, will encourage them to buy.
I'd be grateful if you'd pay my Pinterest board a visit and, if you know any more (like this example by Hackett), please let me know.