There comes a time in every man’s life when he needs to roll up his shirt sleeves for a cause.

I’m not speaking metaphorically!

There are some moments in your day when wearing a long-sleeved dress shirt is inconvenient.

If you don’t have the luxury of changing your clothes to a more convenient shirt, you’ll have to make do. Here’s how to go about it the correct way.

Things to Consider

Before you roll up your sleeves and dive into this topic, a few points are helpful to keep in mind.

wearing a dress shirt with roll up shirt sleeves

The most important is whether rolling up your shirt sleeves is appropriate when wearing a dress shirt.

Rolled shirt sleeves alter your silhouette. When you roll them up, it takes your arm’s outline from slim and sleek to curvy with a couple of lumps.

One of the most important factors to remember is that rolling your shirt sleeves will likely cause them to wrinkle.

So if that could potentially cause an issue later in your day, you’ll need to reconsider the idea.

When to Roll Up Shirt Sleeves

Rolled-up shirtsleeves aren’t always appropriate, so it’s essential that you evaluate your situation and surroundings first.

add black leather watch and black leather bag

You’ll want to roll them up when the weather is sweltering or if your office is very hot for some reason.

Men often roll up their shirt sleeves when they are relaxing. Rolled shirt sleeves have a looser feeling, which is preferable when you aren’t working.

white-blue striped shirt with rolled up sleeves

It’s also essential to roll up your shirt sleeves when doing some manual work. Doing so prevents your movement from being restricted and keeps your shirt clean.

Before rolling up your sleeves, ask yourself whether your sleeves impair your movement in any way? And if you do roll them, will your appearance suffer for it?

Do it if the answer to both questions is “no”.

Rolling Up Sleeves Indicates Casual

There are several methods and styles for rolling up your shirt sleeves, and they all result in a casual appearance. Unfortunately, there is no formal way to roll your sleeves.

Wearing a dress shirt casually by rolling up the sleeves

So if you are at a formal event or work in a conservative office, refrain from doing anything that makes you more casual, even if you’re hot.

You know the old slogan, “Never let ’em see you sweat”? That still holds for formal settings, but I should add, “Never let ’em see you roll.”

Again, it won’t look professional.

And don’t put your suit jacket back on after rolling your sleeves. You may think you’re covering up the evidence, but people will still be able to see the outlines of your shirt sleeve rolls under your jacket.

Dress Shirt Cuff Type

Some dress shirts have a cuff style that may make it more difficult to roll up.

For example, French cuffs can be challenging. Because they are more open than other dress shirt cuffs, they take more wrangling to get them to look neatly rolled.

french cuff shirt style

Also, you’ll need to remove your cuff links before you can roll your shirt sleeves; you risk losing them if you don’t have a safe place to stash them.

Dress Shirt Material

Some dress shirt fabrics roll better than others.

For instance, it is important to think about how wrinkled your dress shirt may get. Some materials crease much easier than others.

Linen is one of the worst offenders for wrinkles. So unless it’s appropriate to keep your shirt sleeves rolled up for the rest of your day, linen isn’t a good choice for rolling shirt sleeves.

white linen shirt with rolled up sleeves

Some materials may not roll well; some feel more slippery than others and won’t stay in place. The more sheen your dress shirt has, the more sliding you will likely experience.

Cotton and linen are two fabrics that stay put very well.

How to Roll Up Shirt Sleeves: The Basic Method

You know that anything referred to as “the basic method” will probably be the most straightforward approach. That sure holds for this way of rolling up shirt sleeves.

how to roll up shirt sleeves: the basic method

This method of rolling your shirt sleeves isn’t very stylish, but it is effective. It’s best for when you are doing labor because you can easily roll your sleeves past your elbows.

This is also a simple way for the uninitiated to roll up shirt sleeves. Beginners are most likely to employ the basic method for rolling shirt sleeves.

Loosen the Shirt Buttons

Open up all the buttons on your shirt sleeve, including the cuff buttons and the gauntlet button.

The gauntlet is an extra button several inches up your arm above the cuff. It secures the opening in the sleeve so that the wearer’s wrist remains covered.

the basic method: step 1 is to loosen both shirt buttons

Note that not all shirts have a gauntlet, particularly higher-end dress shirts.

Unbuttoning your shirt sleeve buttons opens up your sleeve, making it looser, therefore more manageable, to roll. So if your sleeve is too tight, you’ll find it difficult to roll.

Use the Shirt Cuff as a Measuring Point

The length of your shirt cuff is the perfect width for your roll.

the basic method: step 2 is to use the shift cuff as a measuring point

And with the seam marking the end of the cuff, it creates an easy tool to keep your roll line straight and both sides even.

In addition, your cuff seam creates an even edge as you roll.

You’ll fold your cuff over itself for one full cuff length. Use the stitching the same way you use perforated edges. The seam will make folding at that spot very simple.

Roll Up Several Times

You can decide how far up your arm you want your roll to sit.

the basic method: step 3 is to roll up several times

Between two and four times is the best amount for rolling your shirt sleeve, depending on your preference and the width of your shirt cuff.

You may stop at any roll, but remember that more rolls mean a more casual appearance.

Repeat this process on the other sleeve.

After each roll, give a quick tug to smooth out the fabric and keep your cuffs even. This can prevent your shirt sleeves from getting bunched up.

How to Roll Up Shirt Sleeves: The Master Method

The master method, sometimes referred to as the Italian cuff, is a fashionable option for rolling your shirt sleeves.

how to roll up shirt sleeves: the master method

It is an excellent roll for dress shirts with cuffs with contrasting lining. It shows off the contrasting fabric nicely.

The master method for rolling your shirt sleeves is a loose option, but it holds your shirt sleeve securely. It’s a very casual approach to rolling your shirt sleeves.

And as a bonus, this method for rolling your shirt sleeves is very easy to unroll your sleeves quickly.

Loosen Both Shirt Buttons

You’ll need to start this roll by opening all of your cuff and gauntlet buttons.

the master method: step 1 is to loosen the buttons

This is a very exposed style of roll, so you need to open up your dress shirt sleeves as much as possible.

By opening up your sleeve as much as possible, you’ll be more likely to get your sleeve rolled as high as you need it without being restricted.

Roll the Cuff to the End Point

Pick the point where you want your cuff to rest; just below your elbow is generally the best spot.

the master method: step 2 is to roll the cuff to the end point

Then, using your cuff as a guide for measurement, roll it up to a location that is at least two times its width but makes only one fold.

This will turn a good portion of your sleeve inside out, making one very long roll.

Roll Again from the Bottom

Take the bottom of your roll and roll it again up to cover most of your cuff. Leave at least a slim portion of your cuff exposed.

the master method: step 3 is to roll again from the bottom

This way, if the inside of your cuff has a contrasting color or design, you’ll be showing just a hint of it. The rest of your cuff should be covered, however.

Smooth out the material all the way around your arm. Work any creases out from the fabric.

You Can Repeat the Fold from the Bottom

You may keep folding your sleeve until you reach the middle of your forearm. The extra layers of folding your sleeve over itself help hold your dress shirt in place.

the master method: step 4 is to repeat folding from the bottom

This style of rolling your shirt sleeve can be tricky to match exactly on the other side, but it’s critical to ensure that both arms are even.

Bring your roll and shirt cuff to the same level on each arm and show the same amount of cuff on each sleeve.

You’ll need to check a mirror to ensure both sides are a perfect match.

How to Roll Up Shirt Sleeves: The Rubber Band Method

You can use a rubber band as a garter on your arm for a fun vintage look.

how to roll up shirt sleeves: the rubber band and garter method

This fashion looks very tidy and is excellent for holding your shirt firmly in place. In addition, you’ll have no fear of your sleeves unrolling.

And perhaps best of all, people won’t have any idea that you’re using a rubber band as a fashion cheat!

Find Two Rubber Bands

When choosing rubber bands to use in rolling your shirt sleeves, make sure the bands are not too tight. You don’t want to risk cutting off your circulation.

two rubber bands

On the other hand, you don’t want them so loose that they don’t stay in place.

And finally, make sure they are strong. It would be no good if your rubber bands snapped in the middle of the day.

Don’t fret over their appearance, though. It doesn’t matter what they look like because they’ll be well hidden by your shirt sleeves.

Slide the Bands over Your Forearm

Secure the upper part of your shirt sleeve with the rubber band. The rubber band should sit over the middle of your forearm, just beneath your bicep.

The fabric will bunch around the elastic band, making it look a little bit messy. That’s ok! It will be covered up when you roll your sleeve.

Slightly Pull the Shirt Up to Hide the Band

Pull on the sleeve material slightly. This will help puff it out by a couple of inches, therefore creating a fold.

The fold will help hide the rubber band underneath. Be sure you only pull up enough fabric just to cover the elastic.

rubber band method: step 2 is to hide the band

If you pull on the material too much, you’ll wind up with a large fold over the rubber band, which may look sloppy.

Roll the Sleeve from the Bottom to the End Point

Unbutton the buttons on your shirt sleeve cuff and gauntlet, opening your sleeve as wide as possible.

rubber band method: step 3 is to roll up the sleeves

Starting at the bottom of your sleeve, bring it up to just over the rubber band. You’ll be creating one very long roll. Smooth it out all around the circumference of your arm.

Repeat the Fold from the Bottom

You can keep folding from the bottom until you reach the middle of your forearm. Then, fold the bottom edge up to the rubber band line each time.

rubber band method: step 4 is to repeat folding from the bottom

Repeat the process on the other arm. Again, you may need to use a mirror for help, making sure each sleeve is even with each other and smooth.

Alexander Stoicoff

Author: Alexander Stoicoff

Hi, I’m Alex, and I’ve studied and specialized in styling in Rome. Through my writing, I want to help men dress well and learn the purpose and significance of suits and other formal attire. My final goal is to make men more confident in their wardrobe choice and life in general.