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How To Roll Up Sleeves – With Style & Confidence

It’s not something you typically give much thought to. It’s getting hot, you’ve got to get your hands dirty, or the cuffs are slightly too long, so you roll up your shirt’s sleeves.

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Only, you notice wrinkles in the material later, the rolls around your elbows look and feel bulky, and that professional aura you were giving off now seems a little like an unsure college student. Who knew sleeves could do so much?

As with every aspect of your refined, dapper-leaning look, sleeves maintain part of the balance. If something’s a little too tight, a little too loose, or a tad too wrinkled, it skews everything off just slightly, and draws too much attention. So, to make sure everything’s in check, here’s what you should know about rolling up your sleeves:

How To Roll Up Sleeves

Why and When to Roll Your Sleeves

It’s a cliché that you now only spot in old TV shows – perhaps westerns in most cases. Two men get into an argument, and before the brawl starts and the guns come out and, well, they roll up their sleeves.

Aside from the fact that button cuffs hitting right at the wrists prove rather restrictive, clothing in decades past was rather expensive, and men – even those about to fight – were loathed to damage the fabric.

Too, in the decades before stain and abrasion resistant fabrics, you had to be conscious of dirt and spills. From dress shirts to long-sleeved workwear, men – and people in general – wanted the greatest bang for their buck.

While a rip or tear might have meant a few stitches or a patch, stains you couldn’t get out essentially ruined the garment.

How To Roll Up Sleeves

Eventually, in defiance of etiquette, rolled sleeves conveyed a going-against-the-grain sentiment. College students, roughly midcentury, would roll their sleeves just below the elbow, and swing their jackets over their shoulders.

In films, stars of the era – James Dean and Steve McQueen, to name a couple – intentionally rolled up their cuffs to signal a mix of rebellion and masculinity.

Historical context and garment construction aside, social rules have loosened somewhat and garments resist stains and wear better, but rolled sleeves – especially those bunched up past the elbow – remain taboo in a handful of instances.

How To Roll Up Sleeves

At Work

In creative or casual environments, you’ll get a pass. In those where you’re still expected to wear a suit? Proceed with caution. In these instances, think about:

How Hot Is It? If you – and others – can feel the heat, you’ll likely be granted some leniency regarding your sleeves. Just don’t have a short-sleeve shirt under your sportscoat.

Will Your Shirt Wrinkle? If you can answer “no” – and with an appropriate fold, that should be your answer – a fold or two, until you have to button your cuffs, is perfectly fine.

How Casual Your Workplace Gets. Is it only business dress when the top-level executives are there? Or, do you occasionally spot your boss – or your boss’ boss – in a polo shirt and chinos? In the latter scenario, no one will blink an eye when you tastefully roll up your button-front’s sleeves.

How To Roll Up Sleeves

Other Factors

Aside from reading the room, be sure to think about:

What You’re Wearing on Top: If it’s a blazer or sportscoat made from a thicker, textured material, the rolls will reveal a bulk underneath. As a general rule, roll your sleeves down before you put your coat back on for a more professional silhouette. And never fold your blazer and cuff together – unless you’re intentionally alluding to an ‘80s trend.

How Far You’ll Be Rolling: If you’re strictly thinking about temperature, roll the sleeves so that they fall right below your elbows. A roll or scrunch above, on the other hand, signals that you’re about to do some work.

Buttons and Cuffs: As we've mentioned, don’t accidentally create permanent creases and wrinkles. Be sure to unbutton your cuffs and gauntlet first then create a perfect fold starting with the cuff. Never bend the cuff as you’re rolling up your sleeves. And of course – remove cufflinks before folding the cuff over.

Length: Always keep the sleeves even – down to the number of rolls and where the folds fall. Generally, leave a few inches of wrist, but keep the elbow tucked inside. On this note, if the sleeves are too long by themselves, realize that rolling the cuffs can only do so much before it’s obvious you’re wearing the wrong size.

How To Roll up Sleeves: 3 Cool & Unique Ways

Single Fold With The Cuff

Called an “AIFA” or “Marine” roll, this method is perhaps the most straightforward and follows the rule of thirds. Specifically, this relatively short roll only leaves one-third of your arm showing.

After you’ve unbuttoned the cuff and gauntlet:

1. Flip the cuff back

2. Fold the cuff fully over into a fold of fabric. At this point, you shouldn’t see the cuff. If you’d like a higher roll, fold it over once more.

3. Fold the corners of the cuff in, so that the roll stays in place but doesn’t feel too tight.

4. Don’t smooth out the fabric. A few wrinkles hint at its relatively casual nature.

How To Roll Up Sleeves

Inside-Out Sleeve

Frequently called the “Master Roll” and on occasion the “Italian Roll,” this method is ideal for highlighting contrasting cuff material. On a practical level, it gets the sleeve out of the way without using too many folds, consistently holds it in place, and unrolls without creating as many creases.

After you’ve unbuttoned the cuff and flipped it back:

1. Bring the cuff nearly all the way to your elbow. Your sleeve should be inside-out at this point.

2. Smooth out any wrinkles or creases.

3. Using the flipped sleeve, roll the material evenly until it overlaps with the very bottom of the cuff. You may need to hold the cuff down as you fold.

4. Ideally, you should finish with just the top portion of the cuff exposed, and the shirt falling roughly an inch below your elbow.

Man with sleeves rolled Inside out

Rolled Up All The Way

The most basic out of all methods listed here, this option simply involves cleanly rolling up your sleeves until they hit at or above the elbow. In this case:

1. After unbuttoning, flip the cuff up.

2. Fold it back, using the cuff’s width as a guide for each roll.

3. Continue doing this motion, until the sleeve sits at the desired height.

4. As you go up, straighten the fabric each time to avoid any bunching, bulk, or wrinkles.

Man rolling up sleeves

With a Garter

A method relatively out of style and used only with dress shirts, the garter appeared mid-20th century as a way to keep sleeves in place on the job. The approach proved to be effective, factoring in the fact that fabric gets slack over time and the wearer doesn’t want to keep on folding it back.

These days, however, closer shirt fits have made this method somewhat obsolete, although you’ll still encounter them at higher-end tailors.

Should you want to try a garter:

1. Wrap the band around the upper portion of your sleeve.

2. Pull the shirt up a few inches to hide the band.

3. For a cleaner look, try the Master Roll, folding the band into the rolls, ideally right below where the cuff falls.

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how to rollup sleeves with style

Ivan Yaskey is a Philly-born menswear fashion blogger and copywriter. When not writing about men's style he's also an EDM and synthpop enthusiast.