Maybe it's because I grew up in Santa Barbara but I don't see anything wrong with what the guy is wearing in that picture of him sitting in the jeans and polo that people keep making fun of.
I mean yeah, having pants that are pre-worn/bleached/paint-splotched is dumb but that look is just kind of... beach culture. You live in your jeans, they're comfy even if they get fucked up, everyone wears polos or fitted tees, and sandals are the shoe of choice for the surfer beach-goer type, which is obviously the style A&E and Hollister go after. Aside from his weird face, the guy looks like a middle-aged surf rat. Leathery skin, fit, sun-bleached blonde hair, tight polo and ratty jeans with sandals.
I have several Hollister shirts and I've gone through one pair of jeans and am on my second after like 5+ years of wearing them. They're comfortable and when I'm not lazing about being a fatass and am in proper shape, they look really good on me. They're also super soft too @__@ I love them.