Should they or shouldn't they?
It's a question that others have asked.
I actually don't think it's an age thing. But rather a 'looking ok' thing.
Some chaps have never looked anything but a bit baggy or disheveled in jeans. Arguably they were ill-advised to have ever worn them in the first place. But as we ourselves get baggier that's an awkward look to live with. Because it accentuates loss of youth, when scruffy was perhaps the order of the day, or even a post-modern signifier of something. But if you once looked ok in jeans there is a fair chance you still might.
Apologies to 'The Thoughtful Dresser' readers for another music reference, but I saw Bruce Springsteen ( soon to be 59) recently. He has shown no desire to change the way he looks, with denim much in evidence. And he looked entirely sound. Well, sound enough to have a fair number of considerably younger women swooning ( as shown on the giant video screens). But if he hadn't been so energetic, skipping ( yes, skipping) about the stage for two and a half hours, and been quite so trim, then arguably he wouldn't have looked so good.
Small but crucial detail: his jeans fitted.
They don't always . My last two pairs of Levis have been highly unsatisfactory in that department. I bought them whilst in blokeish mode- find the right size, and then a cursory try on, because sometimes a bloke feels too inhibited to be parading around the store being , for want of a better word, vain. Mistake.
As you get older the fit becomes both more problematic and more important. So to get it right you may actually have to apply yourself. And do that thing called shopping.
More on that anon.