I’d like to ask your opinion on something — do rolled-up/cuffed pants make legs look longer, or shorter? I’m 5′ 7″ and started rolling up the bottom of my jeans/pants to look like a cuff, but was told it made my legs look shorter. (All the pants are pretty slim cut.) On the other hand, I’ve heard people say rolling up pants, sometimes even to the point where you can see skin/sock between pants and shoe, makes legs look longer.
I found this inquiry to be both interesting and timely. I’ve been seeing more rolled pants out on the street, some done well and others less so. When it looks good, this style can convey a classic and casual ease. Rolled khakis, paired with loafers, a washed oxford cloth button down, repp tie and blue blazer is about as Americana as you can get – very Kennedy clan at Hyannisport. Substitute pressed and cuffed khakis and the look is more dressed up but looses none of its inherent appeal.
Rolled khakis on the beach (r) – a classic look
Rolled jeans are a different story. Jeans traditionally have a simple narrow hem and rolling them can create a nice casual effect with a variety of meanings. A simple turn up imparts additional casualness to your jeans’ already comfortable personality. This look is perfect with worn in, beat up favorites. A wide flat roll easily evokes a 1950’s James Dean vibe or a seaside clam digging feel.
When it come to the effect on height, in most cases rolled-up pants can have the same visual impact as cuffed pants. Cuffed pants have a more defined bottom than un-cuffed and therefore give the trousers a clearer visual start/stop line. Due to a cuff’s grounding effect, on short men this can sometimes create the impression of shorter legs. This is especially true with a wide leg or heavy break that leaves the pant leg puddling around one’s ankle.
The same can be said of rolled pants, most notably when the pants are already too long. Once rolled up they look like little life preservers tied around the wearers’ feet. However, in both cases – cuffs or roll-ups – when the pants are trimmer and the length properly chosen, the look can be nicely neutral regardless of one’s height.
Sometimes, the point of rolling your pants is to create a dramatic look, not a subtle one. The picture below, from Ralph Lauren, is a good example. The rolled pant legs are bulky and prominent. In this case, the casual and outdoorsy nature of the model’s cargo pants can comfortably balance the look.
Matching the roll to the pants
On taller men, the problem of puddling can hold true, though the impact is less severe; there simply is more leg to balance out the mass of fabric down at the shoe. It is also easier for tall men to accentuate their height by tailoring pants with no break or even having them hemmed or rolled slightly too short. As my reader correctly points out the exposure of a little sock or ankle implies height via the leg being longer than the pants. Though it seems fairly simple, this can be a tricky thing to pull off and can sometimes come across as an affectation.
An example of elegantly rolled jeans
Whether you are short or tall, make sure that the roll is only one or two folds deep at the most. Unless you are specifically trying to capture that rumpled walking-along-the-beach-at-the-Cape look, you want the roll to be neat and hold its shape.
Personally, when rolling any pants, I also try and avoid it looking too manicured and perfect (often the cause of that unintended affected appearance). If I really want cuffs, I should go see a tailor.