Before we begin, lets get one thing straight: You’re not rolling up a dress shirt. While an oxford sleeve should be trim and tidy, a rolled-up tee is supposed to look disheveled—like casual bedhead, or a linen suit. With that in mind, don’t overstress, or feel the need to repeat and repeat. It was probably right the first time.
Now, on to the gun show. To ensure that your sleeve stays properly rolled (a common stumbling block), wrap an elastic band around the based of the unrolled sleeve. The elastic will keep each roll in place while remaining out of sight.
Finally, unless you’re committed to the greaser look, resist the urge to roll all the way to the shoulder. Two or three rolls should be more than enough to capture the classic look, as our man Gosling demonstrates.
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