Rolling up your sleeves.
It's something you've probably never thought twice about.
But the way you roll your sleeves makes a huge difference in the silhouette of your outfit. It can keep a level of formality in hotter weather. Or it can take your outfit to business casual. This simple art – which takes a few minutes to master – makes a world of difference to your appearance and the social signals you send. (And it can also make your arms look bigger!)
But you need to know how to do it right. In this article and video, I’ll explain how to roll up your sleeves in five different ways. You can decide which method suits you best.
Let's start with a bit of context. Historically, men have rolled up their shirt sleeves in preparation for work (or an occasional fight) because clothing was expensive and they didn't want to damage it.
Watch any old Western film and notice how men take that extra moment to carefully fold their sleeves before landing a punch!
Sleeves would also be rolled up at the end of a long day as men headed to the bar for a drink with their mates.
In the modern world – the act of rolling sleeves has evolved into a style statement.
The way you roll your sleeves indicates:
Cooling off in hot weather. Rolling up sleeves allows air to directly flow over more of your skin.
A relaxed attitude at the end of a hard day's work. Rolled up sleeves can dress down a formal outfit.
Preparation for physical labor. Rolled up shirt sleeves are the universal symbol to indicate men at work.
While some may argue that there is one particular right way to roll up your shirt sleeves, I suggest there are several methods and depending on the situation you find yourself in – one of them will be better than the rest.
Should your sleeve stop above or below the elbow?
The simple answer is: above the elbow if you’re about to do work. And below the elbow if you’re just cooling off and want to let in some air or to signal that it’s the end of the day.
5 Ways To Roll Your Sleeves
For all the methods listed below, the first step is to undo the buttons on the cuff and gauntlet of your shirt. You'll find a gauntlet button halfway up the sleeve opening on most good shirts. The openings are there to allow for proper sleeve-rolling and cuff-ironing – if they're long enough to serve their purpose they'll be too long to stay closed without a button.
#1. The Master Roll
Modern sartorialists accept the master roll as the preferred way to roll up sleeves. But I find many men have never heard of it.
Roll up the sleeve to about two widths of the cuff.
Smooth any creases or folds in the fabric.
Roll from the bottom end of the sleeve once more to cover the cuff, leaving only the top end of the cuff exposed.
If the inside of the cuff has a contrasting color or design, show just a hint of it and cover the rest.
Hold the top edge of the cuff and pull down to undo the fold.
Pro Tip: This is how to roll up sleeves when your shirt has a contrasting lining or design pattern on the inside of the cuff. The striking contrast is visible ONLY when you use the master roll. Show off the chambray inner cuffs on your flannel shirt.
This is my favorite method to roll shirt sleeves for the following reasons:
It's the least restrictive. It gets the sleeve completely out of the way – allowing for natural arm movement.
The sleeves are locked in place and won't come undone as the day progresses.
Unrolling the sleeve is simple and quick.
It keeps the whole appearance neat and in place.
#2. AIFA Roll
The AIFA roll screams casual. This is the easiest technique to fold your shirt sleeve.
It adheres to the rule of thirds – a design principle that has implications in men's style too. In the AIFA roll, the sleeves expose only a third of your arm. This ratio is visually appealing according to the rule of thirds.
Fold the bottom of the sleeve once, about the width of the cuff.
Using a similar width, repeat a second time with the folded cuff.
Avoid smoothing the fabric. The AIFA roll is supposed to look casual and effortless.
The AIFA roll is suitable for men who have short and narrow arms. Rolling your sleeves using this technique will make your arms look proportional to the rest of your body.
This roll ends below the elbow and is perfect for a day out with the family – with a dress shirt and your favorite denim. The only problem is that it comes undone quite easily.
#3. The Basic Roll
Also called the ‘Beginner Roll,' this method is the intuitive way to roll sleeves. If you’ve ever watched someone who hasn’t been around people who know how to roll up sleeves, you’ll see them use the basic roll.
Depending on the shirt and fit, the basic roll can be time-consuming. It restricts your hand movements and is difficult to undo.
Using the cuff as a measuring point, fold the cuff once.
Repeat the first step several times, tugging at the fabric to make sure it is straight and smooth.
Roll up until you go past the elbow.
The Basic sleeve roll is suitable when your shirt sleeves are considerably wider than your arms. The extra fabric is required for the third fold.
Some casual shirts feature a button or thin strip of fabric on the inside of the sleeve to secure a basic roll.
#4. The High Roller
Do you have upper arms worth displaying? Then consider yourself a high roller when it comes to how to roll up sleeves.
This method suits men with big biceps and tattoos on their arms. The sleeves are rolled well above the elbows.
It’s also great for manual work and gives you a laidback look.
To achieve the high roller look, fold your sleeves before slipping into your shirt.
Lay your shirt down on a flat surface.
Fold your sleeve about a cuff width.
Follow the same step a second time, covering the folded portion of the cuff.
Roll the sleeve a third and fourth time to cover the entire cuff.
The High Roller can also be achieved while wearing a shirt and works best with semi-casual or informal shirts.
On more fitted shirts, this technique looks like you have a bagel stuck on your biceps. The Master Roll is better suited for fitted formal shirts.
#5. The Garter Roll
Over time – the shirt sleeve tends to lose its elasticity. They tend to unroll and create some frustration especially if you are doing something important. Like helping the wife with the dishes.
New York restaurant waiters in the 1960s found a smart solution. They worked out how to roll up sleeves and secure them with a sleeve band or sleeve garter. This holds the folded sleeve firmly in place.
The sleeve band disappeared for a few decades and regained popularity after soccer player David Beckham used them to give his sleeves a slim and neat appearance.
Sleeve garters are generally elastic, but you can also find metal and silk ones in a range of colors and patterns.
Garters will make your sleeve-rolling a whole lot easier and give you a retro and unique look.
Here's how to roll up sleeves with a garter:
Secure the upper part of your shirt sleeve using a sleeve band.
Pull the shirt up few inches to hide the sleeve band under the shirt folds.
A bonus option is to secure a master roll using a sleek and smart metal sleeve band.
A strong rubber band can also be used. Ensure the band is hidden in the shirt sleeve folds. Shirt arm clips are an elegant alternative to sleeve garters. This variation of the garter looks like a tie clip and is an acceptable piece of jewelry that sits vertically on your arm. Roll your sleeves up following the Master Roll method, then insert the arm clip facing out. Garters and arm clips are great props for conversation starters at parties.
BONUS – Tips To Improve Your Sleeve-Rolling Technique
Ensure that the rolled length on each arm is the same.
The sleeves should stop above the elbow if you’re about to do work.
Roll your sleeves below the elbow if you’re just cooling off and want to let in some air or to signal that it’s the end of the day.
Iron or press your shirt before rolling the sleeves to remove any creases.
If you find yourself rolling your shirt sleeves either because they are too short or long, my advice would be to find a good tailor.
When Can You Wear Rolled Sleeves With A Tie?
In general, avoid wearing rolled sleeves with a tie. These are two contradictory style elements. Rolled sleeves indicate casual style while a tie leans more towards a formal style. But I can think of two occasions when it's appropriate to roll up your sleeves when wearing a tie.
#1. When you want to prevent them from being damaged or getting dirty. So if you're going to be working with your hands – moving office equipment or anything that could tear your sleeves or get them dirty – roll up your sleeves and get to work. And you don’t even have to take off your tie.
#2. When you want to signal that you're off work or it's time to relax – especially if you're the boss and others are taking their cue from you. In that case you’re not just going to roll up your sleeves but you’re also going to loosen your tie. Take your jacket off.
A great example of this was Obama at the beer summit. He'd invited a professor who'd been wrongly arrested, and the police officer who arrested him, for a beer with himself and the vice president. There was definitely a bit of raised tension there.
If you look at a picture of the four of them you can tell that Obama is trying to send the signal to relax. He has his sleeves rolled up and his jacket off. He's saying, ‘We're just four men having a casual beer together, let's talk.' But both his guests are respectfully keeping their jackets on.
Shortening your shirt sleeves can be fun, irrespective of the season. Experiment with the various methods listed above and mix it up so you are not stuck with the same styles.
The length of your shirt sleeves can really have an impact on the whole outfit, so it is important that you get it right.