Rolling sleeves used to be simple. For most of the 19th and 20th centuries, men would roll up their sleeves to cool off or fight. There were no conversations about the right way to roll your sleeves or when it was acceptable to do so. If you felt like it, you shoved your sleeves up. No style, no question.
Today, the eyes of judgement are strong in the world. The rise of casual fashion has ended our naiveté about rolling sleeves. We are expected to know an extensive list of sleeve styles and use them correctly every time. Fortunately, we have a wealth of sleeve rolling wisdom up our sleeves. Sleeves haven’t beaten you yet.
Rolling sleeves never seemed so easy. Fold up once about the width of your cuff, then fold up a second time at a similar width. This sleeve style abides by the rule of thirds, which dictates that an image should be imagined as divided into nine equal parts. Honestly, this is just a complex way of saying the AIFA roll should expose one third of your arm. Rock that one-third-naked arm at your neighbor’s barbeque or a family picnic. The fashion gods will be pleased.
The art of sleeve rolling is incredibly precise. The difference between an AIFA roll and Basic roll is literally, a roll. Fold up once the width of your cuff, then continue to fold up at a similar width until you uncover your elbow. The Basic usually requires three rolls. Some people complain the Basic roll is time-consuming, even restricting. It certainly works best with thinner shirts. Thick flannels will bunch up and feel bulky. Remember to undo your cuff buttons, otherwise you’re in for an annoying struggle.
We hope your motivation for learning how to roll your sleeves is not an advancing gambling problem. If it is, at least you’ll have sexy sleeves while you play away your livelihood. The High Roller is just one more roll of the sleeve than the Basic. Farewell rule of threes! Now we’re working in quartets. The High Roller often incites arguments about how far up to roll your sleeves. Why add an extra roll just to reveal your forearms? Unless you sport big biceps and hefty tattoos, the effect is pretty underwhelming. We’re not saying steer clear of the High Roller, but if you haven’t been hitting the gym or have some skin art to display, be weary. You’ve been warned.
The Marine roll is the High Roller’s inside-out twin. For a Marine roll, bend your sleeve upward at the cuff, then curl it until it’s inside out. Repeat this step until you reach your desired length. The Marine roll is a difficult sleeve style to justify unless you are actually in the barracks. Every day materials crumple as you roll. You can’t do it properly without taking off your shirt. Basically, the Marine roll will have you stripping to bunch up your sleeves until they dwarf your arms. Yeah. Justify that.
It was getting pretty hopeless, wasn’t it? Either you arms were too scrawny, or the look was too casual. In fact, we wouldn’t be surprised if you were about ready to shove up your sleeves and punch whoever decided rolling sleeves was an art. Before you resort to violence, let us run the Master by you. Roll your sleeve up roughly two widths of the cuff. The edge of your sleeve should line up with your elbow. Then, roll the bottom up one width over the cuff. If there is a contrasting color on the cuff, leave a sliver of the top exposed. It’s firm, it’s refined, and to undo it simply hold the edge of the cuff and pull. Do we hear a sigh of relief? Good. No fashion fisticuffs today.
If you fell in love with the Master roll like we hope you did, the Garter may seem superfluous. The word ‘garter’ is probably giving you second thoughts about this paragraph already. We must be thorough, though. Back in the 50s and 60s, shirts didn’t have buttons at the sleeves. What would you do if your sleeves were too loose to stay properly rolled during your daily routine? Yes, we’re asking you what you would do if this entire list were useless. If you were a waiter in New York sixty years ago, you would invest in a garter. The Garter roll’s strength is functionality. Wrap a band around your upper shirt sleeve and pull the shirt up a few inches. Stop when the band disappears under your shirt folds.
There you have it. The six proper ways to roll your sleeves, as dictated by 21st century casual fashion. Now, you can go about life confident your sleeves won’t embarrass you. We can’t guarantee the Master roll will land you your dream job. Your neighbors may still hate you after you roll an AIFA at their barbeque. That clothed torso might get an extra glance or two though.
— Timothy Vest