The high-water look is back, not for classroom popularity or less-than-legal purchases, but for high fashion! This masculine shabby chic style is currently being sported by trendsetting ankles from coast-to-coast. The look is likely attributable to 1. the ongoing style romance with a slightly impoverished look, in which one imitates the togs of an artist squatting in a loft in an abandoned factory and separated into different “rooms” with the help of thin partitions and 2. the popularity of shoes and sneakers for men and women alike. Don’t hide those bad boys under boot-cut cuffs! Show them off! By the way, there are several don’ts. No formal shoes. No rolled-up skinny jeans. No wool pants — the rolls won’t stay. No bootleg pants, which should be burned anyway. And since rolled pants are meant to look casual, nothing about the outfit should be dressy, at the risk of looking too studied. While you’re at it, stop trying so hard.
In the summertime, a nice set of rolled cuffs is also a great way to keep cool while out on the street or warm up again once you get into a chilly air conditioned office or movie theater. Style arbiter Jim Moore, GQ’s creative director, urges that the roll should look somewhat unintentional. Given the unlikelihood of accidentally rolling up one’s pants, Mr. Moore offered some clarification: “You have to channel Johnny Depp for that moment and ask yourself, "How would Johnny Depp roll up the bottom of his pants?” If you still can’t figure it out, you might ask Mr. Depp about shorts.