My BF is 51. He is stylish, but not trendy. We have a friend who will be turning 40 next month and he *is* trendy. The blingy pocket jeans and Affliction shirts, etc. I think it started when he was managing the Cabo Wabo bar in Harvey's Casino and living the 'rock star' life with the Hagars lol. Anyway, I could *never* get my BF into what his friend wears, nor would I want to ha ha. But updating from the tapered, light wash Levi's had to happen several years ago. I basically said," look, this is way outdated" and bought him some True Religions Now he has 2 more pair of updated, but non blingy, Citizens of Humanity jeans and he looks sharp!