It may be because of the hot and humid weather or a preppy undertone that is penetrating into street fashion, but more and more men are starting to roll up their sleeves and I’m not talking about their shirts. I started doing it early spring to give a dapper look to my everyday style. I took a pair of J. Crew’s broken in chinos and paired them with a brown leather belt and a white shirt and some dirty converses. Before I would walk out the door I would bend over and start cuffing each pant leg. At the time, it seemed like I was the only one doing and I definitely felt a little strange with my bare ankles visible for the world to see. You must understand that before then, I never wore shorts unless it was for a sport-like activity. I didn’t find the appealing in any way. It was the age of the “baggy” look and I had never been associated with that.

As I began to roll up my pant legs it started as a mediocre glimpse of my “chocolate” ankles. As spring continued and the trees started to blossom, I began to feel more comfortable with the cuff look and started to become more adventurous. I would begin cuffing them all the way up until they reached my the top of my calves. Then I began to cuff one up and the other down in a bike messenger style. But with each trend that I quickly catch on to, as the masses also begin to follow, I slowly get turned off by it. So although, I enjoy that the rest of the nation is now catching on to this trend, with a recent New York Times article giving it a special spotlight, I’ve personally moved on.

Not to say that I don’t roll my sleeves any more, but I’m less extreme choosing only to roll one leg, but even then it’s moderately.