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Photo credits: The Sartorialist, Street Etiquette, Andrew Jacobs

by Andrew Jacobs

John Fairchild, founder of W Magazine, once said, “Style is an expression of individualism mixed with charisma. Fashion is something that comes after style.”

When I walk the streets of New York or London, the people that catch my eye are not the ones wearing the most expensive clothing, but the ones who do something different; the ones who make even the simplest of garments look unique. For me, style is in the details.

I am no style expert, but I do sincerely believe that any guy, with even the most basic clothing, can look better if he plays with details. Style, after all, is an expression of individualism and, believe it or not, reflects a part of your personality and character.

With spring on everyone’s mind here in Madison, I thought I’d begin with something I love to do when it’s not quite warm enough for shorts but I still want to fit in with the season. It’s time to show off a bit of ankle. I think most guys get stuck in the mindset that you can either wear shorts or long pants with no third option. For me, that couldn’t be further from the truth. For those chilly spring days, it looks great to roll up your jeans or chinos and show off a bit of skin.

The easiest way to do this is to simply roll up each pant-leg a few times, leaving three to four inches between the bottom of the pant and your shoes. If you want to do things a little differently, you might want to try what is called pin-rolling.

To do this, take the inner seam of your pant and tuck it inwards instead of upwards so that the pant is tight against your leg. Hold this tuck in place and roll up a few times, keeping the bottom of your pants tight against your leg. Instead of the roll matching the width of you pant-leg, it is now tight against your leg and gives off a very tapered look. Obviously, however, pin-rolling only works well with a pant cut slimmer through the leg.

To complete the rolled-up look, wear a low-cut casual shoe with no socks. If you’re going somewhere that requires you to dress up a bit, roll up your linen trousers a couple inches, throw on some suede bucks, and leave your socks behind.

If you don’t want to be the guy freezing his ass off in shorts, but still want to show off your spring state of mind, I encourage you to show off some ankle!