From my mid-20s through my early 30s (~1986-93), rolling one's straight-leg jeans up enough to show off one's big boots was a hot look. It combined the Skinhead look (which, in its earliest stage was an Anarchist, not Fascist thing) combined with a street-savvy coolness and trendy hipness. It kinda died when Doc Martens' popularity waned and everyone started wearing baggy jeans. It was completely dead with the re-introduction of flared-bottom jeans about eight years ago; I was the night manager of a trendy boutique on FtL's version of Rodeo Drive and there wasn't a single pair of men's straight-legs in the store. The momentary fad of skinny jeans brought straight legs back, but they were too tight to roll or wear boots underneath. I've started noticing a return of steel-toed Doc Martens back about 8-9 months ago (except among certain fetishists for whom they never went out of fashion) and have seen more than a few younger guys beginning to wear their jeans either with enormous (4-5") cuffs or actually rolled to a point just above their ankles again. About 10 days ago, I was out having dinner with a friend and decided to try it (for the first time in over 15 years). Though I don't currently own a pair of Docs, I do have a nice pair of police-issue 18" boots that I combined with a pair of dark, straight Diesel jeans rolled up to about 5" off the shoe; it felt great and looked somehow very fresh, especially as I was wearing a simple (not overdecorated, douchey T-shirt) and was consciously not aping the Skinhead cliché of braces (suspenders) and too-tight polo shirt. Is this a trend you've noticed where you live? Would you attempt it yourself?