The act of rolling up your shirt sleeves isn’t something that’s given much thought—but perhaps it should be! Like most style choices, rolled-up sleeves have practical roots. For blue-collar workers and weekend warriors, rolling up one’s sleeves is a signal that work is about to be done. From John Wayne to James Bond and even the paper towel man, the image of men rolling up their sleeves says, “we mean business.” After all, you don’t want long sleeves to get in the way of hands-on work.
For those who spend their days in the office, rolled-up sleeves usually signify the opposite: Time to unwind. Unbuttoning those cuffs and freeing your forearms is a universal code for “somebody get me a martini.” So, how do you perfect your own sleeve rolling? We’ve got you! Follow along for expert advice and find lots of long-sleeve staples at Lands’ End.
Whether you’re gearing up for an afternoon of chores, loosening up after work, or attempting to cool down at a summer event, these five rolling options will have you covered. (Note: All of the following techniques will require you to undo all cuff and gauntlet buttons).
The Master Roll
For a locked-in look that’s also effortless, the master roll will be your new best friend—try it on your favorite flannel shirt for a distraction-free fit. First, roll up each sleeve to about two cuff widths. Take the time to smooth away any creases or bunched fabric. Next, roll up from the bottom once more until the cuff is almost covered. Adjust as needed until you have your desired amount of cuff peeking out. For dress shirts with contrasting linings, this roll is especially nice to highlight that contrast. But best of all, this roll is one that won’t come undone until you want it to. Try the master roll on any long-sleeve flannel, cotton or linen dress shirts, chambray, and even thin sweaters.
If you’re feeling casual or in a hurry, the AIFA roll is the way to go. Simply fold up the width of the cuff, and then do so one more time. There’s no need to go out of your way smoothing or adjusting—the style is meant to look relaxed and laid-back. Try this roll with heavier garments like corduroy shirts and denim jackets for more staying power. With thinner shirts, you may need to redo the roll from time to time as it slips.
There’s something we haven’t mentioned yet, but we know you’re thinking it. So let’s talk about the elephant in the room: Let’s talk about Miami Vice. This 1980s TV show isn’t remembered for plotlines; it remains a cultural touchstone for its iconic fashion. Namely, blazers with rolled-up sleeves over pastel T-shirts. Is it possible to recreate this look in the 21st century without being laughed out of the party? We think so!
The AIFA technique should work nicely. When it comes to rolling men’s blazers, opt for lighter-weight fabrics or options without additional lining. Be sure your blazer is tailored to fit you, as oversized shoulders or too much length will have you edging back to ’80s territory. Pair a navy blazer over a beige V-neck sweater for a completely modern take that’s streamlined and ready for work or date night.
The Basic Roll
The basic roll is very similar to the AIFA roll. First, fold the cuff one time. Make sure the fabric is smooth. Fold again, smoothing and adjusting as necessary to avoid bunching. Keep folding and smoothing until the end of your sleeve hits your elbow. This technique works best with shirts that have wider, roomier sleeves (as each fold will get tighter against your arm), and lighter-weight fabrics. Some button-down shirts are equipped with a strip of fabric on the inside of each sleeve to help secure a basic roll.
The High Roller
No trip to Las Vegas required! The high roller style is definitely fit for those who want to show off a little, though—if you’ve got the biceps, you might as well flaunt them. This technique is essentially the basic roll, but you’ll keep folding until the sleeve is well past your elbow. Again, this roll will be most easily achieved with a roomier fit and lightweight fabric like cotton, linen, or flannel that isn’t too heavy. You might also have better luck if you roll before you put the shirt on.
The Garter Roll
Most recently sported on-screen by the Peaky Blinders gang, the garter roll delivers the most retro look of the five main techniques. This one will require a sleeve garter; they’re typically elastic, like a rubber band for your arm, but you can also find ones made of metal, silk, or other fabric. To start, secure the garter over your shirt above the elbow. Pull your shirt in an upward motion above the garter. Lastly, fold that excess fabric you’ve gathered down over the garter so that the garter is covered. Done! As long as the garter is tight to your arm, your sleeve will remain locked in place. While you could pair the garter roll with a casual shirt, it’s intended for more formal clothing and events; use a garter with a dress shirt at the next wedding you attend for a dance-ready look.
Generally, a rolled-up sleeves and tie combo shouldn’t be intentional. If you’re dressing formally for a reason, with a traditional or bow tie, then keep your fit polished with long sleeves buttoned at the cuff for the length of the event. Once you get the go-ahead to relax, however, it’s acceptable to roll up your sleeves. Happy hour after a big work presentation? A tie and a master roll are just fine. Wedding photos out of the way? Bring on the basic roll, or a garter roll if you want to add some vintage vibes. Seriously, keeping the tie on and rolling your sleeves is much better than being the guy with a tie wrapped around his head. Don’t be that guy.
Who knew there were so many different ways to roll up your sleeves? We hope the above has given you insight on this classic styling technique, but just in case you want more, we’ve condensed a few simple dos and don’ts.
Do consider the fabric weight before choosing a roll. Lightweight materials can be rolled higher up along the arm more easily, whereas heavy materials only need a cuff width or two. Do consider the venue or event you’re attending to determine how casual your roll should be. Do consider the activity or work at hand; a higher roll will mean fewer distractions when working with your hands. Do include layers in your rolled look for more visual interest and comfort. Do roll shirts that are too short in the arm but fit correctly everywhere else. Do make sure both sleeves are even in length, no matter which technique you choose. Do feel free to use your own style judgment when it comes to the number of folds—sometimes you just don’t know until you look in the mirror.
Don’t roll fitted dress shirts too high along your arm; you’ll end up looking overstuffed. Don’t pair rolled sleeves with a vest and tie unless you really want to look like a bartender. Don’t roll your sleeves prematurely—for formal or dressy occasions, wait until it’s appropriate to start unwinding a carefully constructed outfit. Don’t rule out a short-sleeve roll! While the top five rolling styles assume you’re working with a long-sleeve shirt, you can incorporate a basic roll with a short-sleeve dress shirt if the sleeves are roomy enough. Avoid going too short unless the 1950s greaser look is your thing. T-shirts, too, can benefit from one casual fold at the sleeve.
With these rolling styles and tips, you’ll be ready to roll up your sleeves like a pro!