Perhaps there is already a voluminous thread on this. But with all the threads featuring pictures of Cordovan Tassle loafers, odes to the bit loafer, or other favorite trad attire...is there a thread showing a plethora of pictures featuring proper rolls on our various beloved button-down collars? I'd start one, but I'm a bit technically challenged and don't have a digital camera. I remember what could only have been an epiphany showing me my fondness for the trad look back in the '70s--when everyone was wearing hideous polyester shirts and leisure suits. I drove past a bill board advertising for a local politician. It was a close up of him in black and white with a perfectly rolled OCBD and rep tie with a four-in-hand knot. Not being anywhere near a Brooks Bros. or the the like at the time, it took several years to locate an OCBD (Gant) and a visit to a larger city where I happened into a traditional menswear shop and found some OCBD Seros and regimental striped ties. Wore them till I was able to move up to Gitman Bros and BB. One look at the proper collar and tie presentation can indeed change a man for life. At least in the way he dresses!
And, of course, the very design of the button-down collar requires a roll of some kind, however minimal it may be. Not all button-down collars will roll the same way, but they will all roll. From there, it's just a matter of opinion on which rolls look good and which don't.
So, to answer stfu's question, it's not so much collar roll that is desired as it is proper collar roll. Just as people have opinions on proper trouser break or proper shoulder padding, they have opinions on proper collar roll.