On a Roll.

Today was a hopeful day in New England. The temperature reached the 50s, a joyous occasion indeed, especially since the sudden snowstorm invasion on Monday seemed to suggest a never-ending Winter. Thus I decided to give myself a little taste of Spring, and I rolled up my J. Crew khakis.

But a somewhat sad realization struck me as I stepped out of my room and into the streets, only to encounter a few questionable glances: not everyone understands the rolled pant. I mean, I should have figured - this is Providence, not Manhattan. But earlier a friend commented, "Vinny, you look like you're preparing for a flood!"; and another asked, "Did you forget to roll down your pants?" For a moment, I felt like I made a complete fool of myself with this particular sartorial choice.

But you know what, at the end of the day I do love my cuffed khakis, and I'll tell you why: rolled, cuffed, or cropped pants - when done correctly (and this is key) - look so smart. Interestingly enough, a friend from London did indeed enjoy the look, noting that the rolled pant is something she sees often in Europe. So maybe appreciating the rolled pant simply requires a refined eye. And rock the right pair of shoes with the look, and your entire aesthetic appeal becomes so irresistibly easy. Today I wore a pair of Gucci drivers, without socks (someone even asked me why I didn't have any socks on!), and felt (for the most part) confident and put together.

I've seen many stylish men carry the rolled pant look, and carry it well. From what I gather, here are some basic tips to sporting the rolled pant: do so with lighter shades and lighter materials, such as khakis and chinos; as far as denim, cuff skinny jeans and roll baggy ones; and again, don't forget the shoes -- tan coloured mocs and drivers, navy and brown boat shoes, and even suede oxfords are all excellent choices.

When I think Spring and Summer, I think simple and carefree. So when the warmth and sunshine finally do come rolling in along with the seasons, I say go ahead and roll those pants up too.