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The Step-by-Step Guide to Rolling up Your Dress Shirt Sleeves the Right Way

Soon, you’ll be on a roll.

Jamison Strong
Expertise:

Style

Jamison is a menswear consultant and custom clothier of five + years, lover of the English language, and firm believer in the power of a well-made suit. A creative individual with passions for menswear and styling, the English language, songwriting, photography, and cooking. Jamison has been writing and reviewing for The Adult Man since early 2024, covering all topics pertaining to the modern gentleman. Read full bio.


Published: Jul 22, 2024
9 min read

Do you wonder why something looks (and feels) a little off when you roll your sleeves?

This how-to guide will have you feeling confident and comfortable when rolled sleeves are necessary.

Whenever a situation calls for them, rolled sleeves can be bulky, uncomfortable, and worst of all—unsightly! 

I’m a menswear consultant and I’ll be walking you through everything you need to know to get rolling with confidence.

Why Roll Your Sleeves?

How To Perform the Italian Roll Step 1

Various situations might require you to roll up your shirt sleeves. Below are three common situations where you might opt for rolled sleeves.

1. To Avoid the Heat

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This is obvious. Second nature, even. When the temperature rises, so do your sleeves. Rolling your sleeves allows for air to pass directly over your arms, greatly improving circulation for cooling. 

Worried about looking too casual? Even in more formal settings, rolled sleeves are typically acceptable so long as you find yourself in direct sunlight.

2. To Complete Common Tasks

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Common tasks such as washing dishes, moving dusty old boxes, heavy lifting, fixing a leak, etc. are all great reasons to roll up those sleeves.

This carries over into the workplace as well. You might be a blue-collar worker who deals with heavy machinery every day. Rolling back your shirt sleeves could actually mean the difference between staying safe and being seriously injured. 

Or maybe you’re a draftsman who needs to roll up your sleeves to avoid smudging your newest plans or getting marks on your shirt.

I work as a menswear stylist and custom clothier. I find myself rolling my sleeves to shine shoes, steam and press fabrics, and move large items around the shop.

You get the point. We all do things every day that make rolling a sleeve the practical choice.

3. To Fit into Casual Situations

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Especially in your best dress shirt, steps must be taken to tone down your outfit for more casual gatherings. Rolling your sleeves as a stylistic choice is a great way to help with this. The relaxed nature of a sleeve roll lends itself well to a more casual setting.

How Much of Your Arm Should Show?

Ultimately, this is up to you. However, there are some things to consider before deciding what type of roll is best for your situation.

Rule of Thirds

If you’re an artist, photographer, designer, architect, or someone in the creative space, you’ve heard of the rule of thirds. It’s a technique used for creating visually appealing images and structures.

It does this by dividing up an object or image into three sections, usually vertically and horizontally. You’ll then place a subject or point of interest on one of the intersecting lines. This will guide your eyes to the subject and is an incredibly effective way to create compelling visuals.

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The rule of thirds has its place in the styling world as well. It is actually a very important component of aesthetic proportions when styling your outfits. 

rule of thirds
Source: Harry Has

With that in mind, you can apply the rule of thirds here by dividing the arm into three sections. Covering one-third of the arm gives a different look than covering two-thirds of the arm.

Minimum Amount of Arm Showing

The Adult Man Brisk Denim Medium Wash Shirt Walking 800

When you roll your sleeve, you want at least a few inches of arm showing. If your shirt fits you properly, this can usually be accomplished by just folding the cuff up once. 

However, if your shirt sleeves are too long, rolling them even a couple of times might not expose enough of your arm. It will still be obvious that your sleeve is too long. 

To fix this, push the roll up your arm or roll the sleeve a couple more times. Long term, be sure to have your shirt altered. A tailor can easily shorten a sleeve so the length is correct before any rolling happens.

Why You’re Rolling Your Sleeves

model wearing GAP denim shirt checking watch

What’s your current situation? Are you trying to cool off on a hot day? Are you getting ready to bury your arms up to your elbows in grease? Or, are you just rolling your sleeves as a stylistic choice?

I covered common situations above where sleeve rolling comes in handy. You get to decide what sleeve roll is best for you at a given moment. 

But take note that your sleeves should never be rolled or pushed up past the elbow unless you will be working. Otherwise, whether you’re in a casual or more formal setting, it is always most appropriate to keep your elbows covered.

Generally, the more arm you show, the more casual you will look.

Types of Sleeve Rolls

There are four types of sleeve rolls I will cover with you today. I will show you exactly how to achieve each one in a few simple steps. You’ll be rolling like a pro in no time!

The Basic Roll (Casual)

The basic roll is the most commonly used sleeve roll you’ll see. It’s intuitive and most likely the way you’ve been rolling your own.

How To Perform the Basic Roll:

Step #1 

Begin by unbuttoning your cuff. Fold the cuff once along its edge where it attaches to the sleeve. The width of your cuff will determine the width of your roll.

Do not fold the cuff itself. Especially on dressier shirts, the cuffs will be stiff as they are lined to keep a clean and formal appearance. Folding the cuff itself can cause permanent creasing. 

With a soft, casual shirt, it’s up to you. But folding the cuff in half can still cause problems, even if it is unlined.

How To Perform the Basic Roll Step 1
Step #2 

Roll the cuff over itself. Be sure to tuck in the fabric to make sure all the edges look neat. At this point, you may need to undo your gauntlet buttons as well. 

Depending on the fit of your shirt, the gauntlet buttons may restrict you from rolling more than a couple of times. Your gauntlet buttons are the small buttons that sit against the back of your forearm. 

How To Perform the Basic Roll Step 2
Step #3 

Continue to roll the cuff over until you’ve reached your desired sleeve length, usually two to three more times. With each roll, tuck in the fabric along the edges to keep a clean and intentional appearance.

Remember, the more arm you show, the more casual the look. Only roll above the elbow when working. In the last picture, I pushed the cuff up higher on my arm, rather than rolling it again.

How To Perform the Basic Roll Step 3

The Classic Roll (Semi-formal or Formal)

The classic roll is a simple go-to for almost any situation. 

It is essentially the same as the basic roll, but you will stop after two rolls.

How To Perform the Classic Roll:

Step #1 

Begin by unbuttoning your cuff. Fold the cuff once along its edge where it attaches to the sleeve. The width of your cuff will determine the width of your roll.

How To Perform the Classic Roll Step 1
Step #2 

Roll the cuff over itself. Be sure to tuck in the fabric to make sure all the edges look neat.

How To Perform the Classic Roll Step 2
Step #3 

Roll the cuff over one more time and smooth out the edges. With the classic roll, keep your gauntlet buttons fastened, if the fit allows. They will help to keep a cleaner appearance for this more formal roll.

My sleeve is too tight for me to make this roll without unbuttoning the gauntlet button. But you can tell by looking at it that it would be neater if I could. 

How To Perform the Classic Roll Step 3

The Italian or Master Roll (All Occasions)

The Italian roll, also referred to as the master roll, is my favorite of the four rolls I’ve mentioned today. I chose the shirt I wore today specifically to show off one of the coolest things about this particular roll.

You can use the Italian roll in any setting.

How To Perform the Italian Roll:

Step #1

The Italian roll begins differently than the previous two rolls I shared with you. Start by turning the cuff inside out. For this roll, be sure to unfasten any gauntlet buttons on your shirt.

How To Perform the Italian Roll Step 1
Step #2 

Without rolling the cuff, pull it up your arm until the bottom of the cuff hits either right at or just below your elbow.

Be sure to let the excess fabric drape below the cuff, over your forearm.

How To Perform the Italian Roll Step 2
Step #3

Leaving the cuff in place, fold the remaining fabric up at the base of the cuff. It should fold over the cuff, but not cover the cuff completely.

This is why I love the Italian roll. That peek of fabric looks so nice, especially when you are wearing a shirt with contrasting fabric inside the cuff.

How To Perform the Italian Roll Step 3
Step #4 

Adjust to fit the length of your choosing. This is my preferred method, even for a “working” length. In the last picture, I simply started with the cuff in the middle of my bicep instead of just above the elbow.

You can pull on the cuff after the roll is completed to let a little bit more of it show if desired. Usually, about one-third of the cuff showing is the sweet spot.

How To Perform the Italian Roll Step 4

Sleeve Garter Cuff or Roll (Semi-formal and Formal)

This last one is for my traditionalist and enthusiast readers. 

Originally invented in the 19th century, sleeve garters have made somewhat of a comeback but really were mostly forgotten for a few decades.

Sleeve garters are usually elastic, but can be found in varying materials, such as metal.

I do not currently own a sleeve garter, but a thick rubber band makes an acceptable substitute in a pinch. That’s what I’m using today.

How To Use a Sleeve Garter:

Step #1

Decide how high you’d like your cuff to sit on your arm. Unbutton the cuff and gauntlet buttons as necessary. 

How To Use a Sleeve Garter Step 1
Step #2

Slip your garter (or rubber band) up over your arm. Let it rest at your upper arm. Usually just above the elbow or around your bicep is perfect.

How To Use a Sleeve Garter Step 2
Step #3

Push the fabric with the garter up your arm until the cuff is at your desired length.

How To Use a Sleeve Garter Step 3
Step #4 

Tidy up the sleeve by folding the fabric at the upper portion of the sleeve back down over the garter. 

You can decide how neat to make this look. Often with a sleeve garter, a slightly messier appearance is normal and even expected. 

How To Use a Sleeve Garter Step 4

Conclusion: Roll Your Sleeves Right

I am a very skinny man, but I tend to run hot. I get warm very easily. Because I wear a dress shirt to work every day, this means I often find myself needing to roll up my shirt sleeves. 

I will always remember how excited I was when I learned the Italian/master roll. In my opinion, it looks the most polished and the most interesting. You are bound to get compliments when using the Italian roll.

But let’s be honest, just a simple single fold of the cuff is an easy go-to for me in many situations. To me, it has an effortless look that I really like.

In the end, style is individual. You do you! I’m a huge proponent of doing what YOU like. 

However, knowledge is power. I’ll give you all the information I can to help you make informed decisions. Create your own unique style, and enjoy the journey while you do.

For more, check us out on Instagram where we serve up simple, straightforward tips for self-improvement.

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