Learn the Best Way to Roll Men’s Dress Shirt Sleeves

Learn the Best Way to Roll Men’s Dress Shirt Sleeves

David Donahue dress shirts now available at www.epicmens.com. Photo: www.daviddonahue.com.

Would you be surprised to learn there is a right way and a wrong way to roll up your sleeves? Apparently, there is, and it’s got fashion gawkers talking. In fact, the topic is so popular, it’s been written about extensively in such powerhouse pubs as GQ, Esquire, Business Insider, and the New York Times, as well as in just about every well-known men’s fashion blog on the internet. It seems simply unbuttoning your cuff and rolling it up repeatedly is not sufficient, especially for all you gents who have shelled out a small fortune on a closet full of high-end business dress shirts. These fitted and stylized semi-formal shirts require a special sort of attention to detail. Interested in learning more? Good, because to ensure your rolled-up dress shirt sleeves look “cool,” rather than “corny,” there are three things you have to know:  when is it appropriate to bare your forearms, which rookie mistakes to avoid, and what – exactly – is an “Italian Roll.” So, if you’re ready, let’s get started.

To roll or not to roll

Men’s fashion writer J.A. Shapira briefly touched on the history of rolled sleeves in a Gentleman’s Gazette article this past June. Originally, rolled-up sleeves were the sole purview of the working class, real men who weren’t afraid to get their hands dirty hauling and toting – whatever it was that needed hauling and toting. Eventually, when it became acceptable to remove one’s jacket in public, ivy league elites picked up on the trend, not because they were actually into manual labor, but because they liked the tough, masculine, devil-may-care image rolled-up sleeves conveyed. Of course, it didn’t hurt that Hollywood mega-stars like Steve McQueen and James Dean also were sporting the look. 

Not much has changed since then. Today, even men who spend their days toiling away in spartan and sanitized offices opt to roll up their sleeves for a variety of reasons, some practical and some admittedly a tad vain. Do you fall into any of the following categories? Left-handed and don’t want to drag your snowy white cuff across an inked page? Cuffs too long, too short, too loose or too tight? Dress shirt got you feeling like you’re wrapped in a straitjacket? Or maybe you want to enjoy a juicy quarter pounder, flaunt your new Rolex, take a washroom break, or cool off in the sweltering summer heat. All of these are legitimate reasons to flip back those cuffs and begin rolling, but the best reason just might be that you look good in rolled-up sleeves. Every fashion-conscious 21st century male knows if you’re trying to attract attention, flashing a hint of a tanned, well-toned forearm is a great place to start.                                                                                                                             

However, while rolled-up sleeves may be appropriate when you’re sequestered in your office cubicle or headed out for a casual lunch, after-hours drink or relaxed evening with friends, there are times when a more conventional persona is required. Appearances should always trump comfort when interviewing for a new job, meeting with clients or bosses, working in a business formal environment, or attending a black-tie event. If this list is incomplete or you’re in doubt, play it safe and keep those sleeves unrolled and buttoned up tightly. The adage that it’s better to be overdressed than underdressed is pretty much undisputed on Wall Street, as well as on Main Street.

Mistakes to avoid

Once you do make the decision to roll, commit to doing it right. The internet is full of cautionary tales about professionals, young and old, who end up looking slovenly, clueless, and combative instead of well put-together, stylish and relaxed. Or worse yet, they wind up looking like a caricature of a disingenuous politician trying to pass himself off as an average Joe. The good news is you can avoid these pitfalls if you adhere to a few basic rules. First, when manipulating those cuffs, always remember to unbutton both the cuff and gauntlet buttons. Then smooth and fold, rather than roll and shove. You don’t want to end up with an ungainly, lumpy wad of material that looks like it’s attempting to swallow your elbow. Second, make sure several inches of your forearm are showing, but stop short of rolling past your elbow. You want to roll your cuffs up far enough so that it looks intentional, but not so far that it looks like you’re brandishing your biceps or angling for a fist fight. And while you’re fussing with the length of your rolled sleeves, check a mirror to be sure they’re even. It’ll just take a few seconds, and it’ll stop you from appearing as though you’re the absent-minded professor type, unless, of course, you are the absent-minded professor type. Third, never roll your sleeves while wearing a vest or bow tie; you could be mistaken for a bartender or well-clad waiter. And finally, to protect your dress shirts from undue wear and tear, never attempt to form a crease in the middle of a stiff cuff and always, always unroll your sleeves promptly after wearing. It should go without saying (but we’ll say it anyway) never squeeze a shirt back into your closet with the sleeves still rolled. To avoid excessive wrinkling and stretching, make it a habit to unroll your shirt sleeves before hanging. Your pricey dress shirts will thank you for it.

Learn to execute the perfect “Italian Roll”

You may have heard of the Basic Roll, the Casual Roll, or even the bicep-hugging Military Roll, but there’s really only one type of roll that should be used with men’s business dress shirts – and Italy’s trendsetters are being credited with its popularity. Mirroring the form-fitting styles that are the hallmark of Italian fashion, the Italian Roll grips the elbow and forearm gently, showing off both to great effect. There’s no need to worry about having to continually roll and unroll your sleeves throughout the day. The Italian Roll, sometimes referred to as the Master Roll, has a reputation for staying put. Yet despite its snug fit, the Italian Roll is also the least constricting of the styles and the easiest to undo. You can go from rolled to unrolled with literally just one tug and very few wrinkles to boot! Best of all, however, is the Italian Roll’s casually sophisticated look and feel. There’s no bunching, crumpling or wrinkling. Instead, the fold is surprisingly smooth and clean, allowing you to move your arm freely and naturally.  And it’s the only roll that deliberately showcases an edge of your dress shirt’s cuff, which adds an interesting touch of contrast if you happen to be wearing a white dress shirt with a patterned or alternatively colored cuff.

Sold yet? Or at least willing to give it a try? Assuming you’re nodding your head “yes,” just follow these two simple steps. First, let your arm hang loose at your side and with your other hand, flip the unbuttoned cuff inside out and pull it up to rest slightly above your elbow. The seam connecting the sleeve to the cuff should be positioned in the hollow of your elbow. A portion of the shirt sleeve also will have been turned inside out. Now for the second step, grab the end of the inside-out sleeve and pull it up over the cuff, securing the cuff in place and leaving a half inch or more of the cuff exposed – for contrast. The result should be a tight, flat roll that covers the elbow, but doesn’t restrict movement. If you’re more of a visual learner, check out one of the many instructional videos on YouTube. And then, of course, practice, practice, practice. It won’t be long before you can do it on the fly, with a beer in hand. We’re pretty sure you’ll be pleased with the results, and when your friends ask where you learned the ins and outs of the Italian Roll, be sure to mention us here at Epic Mens
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