I read his comment differently and took the impression that he was suggesting we all dispose of all of our jeans the day before we turn 36. As for the jeans, they're a pair of Levis that I've had for years. I'm not making an argument for them but I don't remember them as having been given fake distressing. That small point may not make them any more appropriate as 'odd trousers' but I think it does make them a little less cheesy at least.
You're probably both right. I'm wearing jeans today, but not denim and not with a jacket. Whether or not you like my (raspberry, actually!) fil d'Ecosse over the calf socks, is immaterial. I can wear them because I'm a bad muthafucka, at least I believe that's the correct expression.
The thing about jeans is that there is pretty much always a better looking alternative. Whatever dispensation Hugh Jackman might get, it's rarely achievable for mortals like you and me. Unless you're riding a slow motorcycle or a horse, they're not going to look as good as you think they do. What feels familiar and easy and laid back, looks careless, cheap and scruffy. So, really, just trust me on the jeans: wear coloured ones. Or cords or moleskins or best of all some kind of chinos. Perfectly casual, more comfortable, just as resilient and SO much more appealing.
By the way, your pic at the bottom of that picture really sums it all up. That is a rapid transformation from disheveled tryer into comfortably casual serious dude. I like.