I posted about this on the GQF a while back. Here's that post:
I went out and looked at all sorts of expensive jeans. I didn't like any of them enough. I went and bought a pair of Levi's original 517 boot cut jeans in size 34/36 dark hard denim. I normally get a 32-33/33-34 (e.g. 32/34 or 33/34) but these are really hard and the length always shrinks a lot on me and I hate that. I took them home and got in them and then sat down to the GQ Forum for a while. I also did a bunch of bending, squatting, everything that would make creases in them. I then took a piece of 120 grit semi-worn-out sandpaper and scuffed them like crazy all over the knees, on the edges of all the wrinkles, over the fly seam, wallet, and generally everywhere that my real broken-in jeans have lighter parts. I thought I was doing it way too much actually, but now I don't think I even did enough. Then I took them and washed them in HOT water as the label actually says, to shrink them and try and soften them up as much as possible. I let them go thru the rinse but NOT the spin because that will make creases. I took them out wet and put them in the dryer on low for a while. I took them out of there when still a bit damp and ironed the hell out of them. Then I took them still just a bit damp in the waist area where you can't iron well and put them back on. I sat on a towel and went back to the forum or something. Sitting in them when they are wet helps set the creases in and stretch the parts that need to stretch to fit over you, because the fabric is weaker. After I got tired of sitting in damp jeans, I put them in the dryer inside out on HOT to shrink them more. I suggest turning the cuffs way up when putting them in the dryer to prevent vertical creases from magically appearing. It looked like mine had been ironed to have front creases like cowboy jeans, but I caught it in time and they don't show. I then took them back out and put them on, and slept in them, and wore them to work today, and I'm about to sleep in them again tonight. I'll probably do this for quite a while but I am going to hot wash and dry them again soon to shrink them more, and repeat the sanding. I don't know about the whole dirty thing, I don't really like that but I might rub some actual clean dirt (like Southwest trail dust) into them a few times and wash it out. I don't like the idea of the whole things being dirty; that doesn't look real and I think it looks just like your jeans are dirty, not like you actually used them. I'll let you all know how it progresses.
They look really good now. I don't have any tears in them as I wasn't going for that look, but they look and feel like I've been wearing them for years. j.