I remember over a half decade ago my brother passed by a lineup of people waiting to get into a trendy nightclub in New York and referred to them as a bunch of "lemmings" as a result of the fact that they were all wearing trucker hats, which was then the costume de rigueur for that crowd.
I'm always a fan of checking out the galleries posted by GQ "street-style" photographer Tommy Ton, especially in and around fashion week. In his most recent gallery shot outside New York fashion week, I was struck at how uniform these supposed fashion renegades actually looked. There is some irony that their collective quest for individualism actually exposes a group-think mentality.
If there is one trend in particular that was nearly ubiquitous, it was the rising hemline in men's pants, be they dress pants, casual pants or jeans. Sometimes the pants were rolled up, sometimes not, but in almost every case, they "boldly" flouted the rules taught to us by generations of tailors and men's magazines.
So where did this trend come from? In reality, hemlines have been rising for years. Men's designer Thom Browne can definitely be credited with contributing to the trend. His extremely high-hemmed and shin-bearing pants have always been one his quirky trade-marks, and he's been mainstream for over five years now.
Another influence has been the particular cuff style favoured by uber-cool fashionistas in Milan and made famous by the Sartorialist. Here is a photo of one of the the Sartorialist's favourite middle-aged muse, Lino, owner of the Al Bazar men's boutique in Milan.
As you can see, the pants are cut a bit higher so that there is no "break" in the pants as you would see in a traditional hemline where the cuff hits the shoe. The cuff is also wider than a traditional men's cuff. This style is definitely more subtle that Thom Browne's, but it is definitely noticeable.
All of this is to say that rising hemlines have been in the air for some years now, and there are undoubtedly other sources for the trend, apart from the two I identified above.
So what's my opinion on trend? I've actually admired (and tried to emulate) the Milan cuff style for some time now, and I suppose the other styles shown above can be interesting if done properly, but I think the images above show that this style has all the hallmarks of a fad that one should with approach with some caution.