When Lawry was a mere five years old, he had a very traumatic experience: His mother brought him to a "Sportsman Exhibition" in LA County (he's a little foggy on the exact name) where there were lumberjacks, hunters, anglers, etc. showing off their various wares and skills. Tents, rifles, canoes galore. This was 1948 or so. In order to get ample usage out of his "Gold Rivet" jeans (not Levi's unfortunately), his mother bought him a pair that were extra long so that he would grow into them. The catch - an 8" cuff (or roll up). Imagine, you're barely 3 feet tall and your jean cuff is mid-shin. Out in public they went, much to his dismay. Luckily, they were shrink-to-fit, so after the first wash, it was only a 6" roll up. Nonetheless, to this day Lawry is not a fan of the roll up.
The roll up was definitely a hipster look in the 1950s. Today is no different as it experiences a resurgence. It looks great with a pair of sneakers or English brogues. The amount of break is up to you. It looks great on guys and girls (for girls - especially rolled up to mid-shin with a sandal in the summer). For guys, we like a roll up of 3-4". Another benefit, it shows off the selvedge edge for the cognoscenti. So, assuming you didn't have any childhood experiences that would make you do otherwise, give it a try.
Joe loves wearing his jeans rolled down and up.