This image is from September 2008 GQ. I guess this man is mid-forties. As such, he's (apparently) breaking every denim rule in the book; an older man not only wearing jeans (oh dear!), but (worse) distressed jeans.
I like the look, particularly with brown brogues. There's no harm in pushing boundaries. He avoids looking like a middle-aged man dressing like a teenager (to be honest, what teenager would dress like this anyway?) My preference would be for naturally-aged jeans. I don't like the dishonesty of artificially-distressed clothing.
To read more on older men and jeans, go here, For discussion of distressed clothes, see here.
