How to roll long shirt sleeves up and not have them fall down

Some guidelines to begin with

There are some general guidelines to start off with before going more in-depth on the rolled up sleeves topic.

The sleeve length

Rule number one, and perhaps the most important one, is the sleeve length. The sleeves should leave several inches of the wrist visible, to avoid looking like you’re wearing a too big dress shirt that you just had to roll up.

Keep your elbows hidden

Second, the sleeves should not be rolled up high enough for the elbows to be showing. This could risk giving off a sloppy and thoughtless vibe to the overall outfit. Although, is it a practical necessity to roll up your shirt sleeves even higher then you should of course do so.

How to Roll Your Sleeves

There are many techniques that offer various looks. Here are three methods we recommend because they’re slightly more stylish and elegant than the rest.

The Classic Fold

For years, the U.S. Marines have rolled their sleeves. Unlike other folds, the Marine-style cuff is done on purpose, ideally before you put the shirt on. We rarely recommend this as it’s not elegant to wear your collared shirt rolled up all day. If that’s the case, there’s no point in wearing business attire. Just put on a polo shirt and call it a day.

However, if you have the privacy and the need to roll up your sleeves – and you’re wearing an undershirt – quickly remove your shirt and consider the Marine cuff.

This only works with a shirt that isn’t wrinkled. Just as you would place the sleeve while ironing it, flatten out the sleeve on a clean table such as your desk or a dry restroom counter.
At the seam where the cuff of the shirt begins – and with the buttons unfastened – fold the sleeve up with the stitching of the shirt cuff as the seam so the inside of the cuff is now facing out.
Straighten the fold, making sure both the bottom and the top are straight and flat.
Repeat the same process and fold it up once more, duplicating the initial fold.
Straight it out and put on the shirt.

The Italian Method

This style works very well with fashion-forward dress shirts that use a contrasting fabric for the inside of the shirt’s cuff. It adds a bit of sprezzatura to the look and is understated but noticeable at the same time.

While wearing the shirt, unbutton the cuff and fold it so the cuff is roughly an inch past your elbow. This should be a fairly long fold as you are only folding it once.
Next, flip the bottom of the sleeve closest to your hand over so it creates another fold and shortens the length of the rolled cuff. However, make sure that you only roll it about an inch less than the first roll. This way, about an inch of the sleeve’s cuff will poke past the fold. This adds layer and dimension to the roll and showcases a glimpse of the lining’s fabric to add a bold dash of flair to your outfit.

The Quick Roll

This is ideal for a quick trip to the restroom where you need to wash your hands or if you’re worried about mustard hitting your sleeve after getting lunch from the hot dog cart by your office.

Undo all the buttons on your sleeve.
Turn the cuff up just under your elbow and then fold the edge of the cuff by flipping it down into the cuff so it’s tucked in.
Roll the sleeve up by flipping folding it over itself.

This style is far more casual but is quick and easy to do in a time crunch. We don’t recommend doing it for long periods of time, though.

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2. The Master

For the most stylish look, this roll gives you a deliberately casual fold that’s not quite symmetrical and can be adjusted at will.

Unbutton the cuff and gauntlet buttons.
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Flip the cuff back and inside out.
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Pull the flipped cuff all the way to just below your elbow without folding, turning the sleeve inside out as it goes.
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Take the bottom of the inside-out portion and fold it up until it traps the bottom of the cuff.
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Leave as much or as little of the inside-out cuff showing above the fold as you desire.

This looks particularly striking when the inside of the cuff has a contrasting lining. Let enough of the inner cuff show to clearly display the lining, making it clear that you’re deliberately showing off the shirt’s accent as well as rolling your sleeves for comfort. It is also very simple to unfold; just pull and you’re done.

Roll up without wrinkles

By improving your technique it will be easier to create neatly rolled up sleeves without any visible wrinkles to it. Another important aspect is, as always, making sure that your dress shirt is a perfect fit. An ill-fitting dress shirt with bad proportions will most likely also result in badly executed rolled up sleeves with a lot of wrinkles. Pressing or ironing your dress shirt before rolling up any sleeves will also help to get rid of any unwanted creases in the fabric.

Step #3) Fold the Length of the Cuffs

Now it’s time to start rolling up your dress shirt sleeves. Don’t just bundle the sleeves into a ball but, instead, fold them. The proper way to roll up dress shirt sleeves is to fold them the length of the cuff. Most dress shirts have cuffs measuring about 3 to 4 inches. Assuming your dress shirt has similar-sized cuffs, you should fold this amount of material up.

Keep in mind, you may need to fold your dress shirt sleeves two or even three times. Each time you fold the sleeves, though, you should only fold them the length of the cuffs. Continue folding the sleeves until they’ve reached your desired height. Some men prefer to fold up their dress shirt sleeves to their forearms, whereas others prefer to fold their dress shirt sleeves to their elbows. Regardless, you should fold your sleeves the length of the cuffs until you’ve achieved the desired height.

Style

Obviously, it depends on personal preference but in my opinion, rolled down shirt sleeves are just plain old boring.

I always think of boring 9 to 5 white collar workers who hate their jobs and want to kill themselves.

On the other hand, rolled up shirt sleeves look more youthful, masculine, fit and aesthetic. To me, they give off a statement of freedom.

On top of that, they show off your (hopefully) massive forearms and compliment your massive biceps and triceps.

And the ladies love it too. Another reason to just roll them up and rock it.

Me personally, I always roll up my shirt sleeves. Regardless of the weather or occasion. I only keep them down when wearing a suit or a sports jacket.

Try it out and decide for yourself.

Benefits of The Master Roll

The master roll is my absolute favorite technique. There are just so many benefits to it.

The biggest benefit of the master roll is its unique look. Nobody knows how to use the master roll.

You will probably be the only one rocking it and you’ll set yourself apart from the average masses.

Remember, it’s all about polarizing and being unique. The key to being the most stylish guy in the room lies in the details.

The master roll will provide a nice contrast to the shirt color which is why it is perfect for shirts with a pattern or different color inside the cuff.

This subtle but stylish detail will make you stand out a little.

The master roll also looks a lot smoother than the basic roll. There is an air of confidence, freedom and coolness about the master roll that the basic roll just doesn’t have.

The master roll also compliments your forearms even more than a basic roll.

It is superior in terms of speed as well. You can roll up your sleeves and undo them in seconds. No fiddling around. No careful adjusting and folding to make them look neat. Just up, and down.

On top of that, you won’t be left with a ton of creases after you rolled down your sleeves like with the basic roll.

One big advantage for me is the comfort.

As I said, I always roll up my sleeves. I just don’t like my whole arm being covered. It feels restricting. The basic roll still felt restricting because you have to tighten it to make it look good.

That is not the case with the master roll. It sits loosely on your arm and doesn’t restrict your movement at all.

By the way, girls seem to like it too. It might also be my irresistible confidence though.

7 Ways to Roll Your Shirt Sleeves Up

Now that we know what not to do, let’s talk about the right way to roll (FYI, these methods are listed in a logical order of increasing complexity).

The Two Turn (a.k.a., Forearm Hugger)

In general, I think many guys look better with above-the-elbow rolls, but this method is great for a few reasons:

Super quick
Easy to undo
Causes less wrinkling

Here’s how to do it:

Start with sleeves unbuttoned (both buttons, if there are two).

Fold the cuff over itself one more time.

Make sure it’s folded cleanly, all the way around (no twisting).

It looks great on guys with big forearms, but if you have thin forearms, just leave the placket button fastened, as this will ensure the sleeve squeezes your arm a bit.

If you want your sleeve to grab your forearm, button the second sleeve placket button (if your shirt has one).

This is my go-to sleeve rolling method 80% of the time.

This method is also great for more looser fitting shirts (think casual linen button ups during summer).

That said, if you’re wearing a dress shirt, and the sleeves are a bit too loose around your arms, the Two Turn isn’t a good option.

Instead, go for one of the above-the-elbow techniques toward the end of this list.

The Mini J. Crew Roll (a.k.a., The Forearm Kennedy)

This is still a below the elbow method, and it produces similar results to The Two Turn, but the technique is slightly different.

Pull the cuff up to your elbow so a few inches of your sleeve is inside out.

Use your thumb to go all the way around the roll, especially to the thickest part at the back.

Make sure the sleeve is folded over the cuff cleanly.

You should end up with a sliver of visible cuff (about 1/4 inch).

I like this roll because it’s slightly more visually interesting than the Two Turn, but it does take a little practice to get it right.

Keep in mind, if your shirt fabric is a different color on the inside, this method will expose that contrast, which isn’t always desirable.

The J. Crew Roll

Popularized by JFK but somehow named after J. Crew, this is arguably the best way to roll up your sleeves.

It’s quick, clean and stays put all day. Plus, it adds a bit of visual interest by letting your shirt cuff poke out a bit.

It’s like The Kennedy (or Mini J. Crew), just above the elbow. Here’s how you do it:

Pull your cuff up, just above the elbow.

Placing your fingers inside the sleeve, turn it back and over the cuff.

Work your way around the roll so it’s cleanly folded over the cuff.

Leave 1/4 inch or so of cuff poking out the top of the roll.

The roll should be just above your elbow so you can bend your arms without restriction.

When in doubt, go with the J. Crew Roll (a.k.a., The Kennedy) for an above the elbow roll.

It looks good on everyone, it’s easy to do after some practice, and it stays in place nicely.

The J. Crew and a Half

If you have shorter arms, the standard J. Crew roll might leave the roll right at your elbow, which we know is problematic.

To shorten the sleeve a little further, fold the entire roll in half once. You’ll still have the cuff poking out a bit, so you’ll still have that signature look.

Start with the J. Crew Roll, then fold the entire roll in half.

It’s a bit thick, so just try to keep it as clean as possible.

Work your way around to the back of the roll to make sure there’s no twisting.

Done! The roll is half as wide, and it sits slightly higher up on your arm.

The added benefit of this technique is that it creates a thinner roll, which looks more proportionate on smaller guys.

As a short, thin man, this is how I usually roll my shirt sleeves up if I’m going for an above the elbow look.

The “Basic” Roll (a.k.a., the Three Turn)

Unlike the J. Crew Rolls, this basic roll doesn’t take much practice to get right.

You simply unbutton your cuff and roll your sleeve over itself three times. Here are the details:

You guessed it – fold the roll back over itself one more time (for a total of three turns).

The roll is four layers thick at this point, so it might take a little work to iron out any twists.

Use your fingers to make sure everything is clean and tidy.

A sturdy sleeve roll that will stay in place all day long.

Depending how long your arms and sleeves are, this will likely result in an above the elbow roll that stays in place all day.

If your sleeves are a bit longer, this may result in a below the elbow roll, which is okay too.

However, if you’re not happy with where the roll ended up on your arm (i.e., it’s right over your elbow), you have a couple more options

The 3.5 Roll

Just like the J. Crew and a Half, this roll is great for guys with shorter arms, as it produces a shorter cuff.

You do the Three Turn Roll shown above, then fold the entire cuff in half once.

Start with the Three Turn Roll in place.

Fold the roll in half, all the way around.

The result is a shorter, thicker roll that sits higher up on your arm.

As a shorter guy, I like to use this method to ensure the roll clears my elbow. I also like the mini cuff it produces.

The Quadruple (a.k.a., El Cuadruplicar)

Finally, if you have very short arms or very long sleeves, you may need to use the mack daddy of all sleeve rolling methods.

It’s not the Three Turn, it’s not the 3.5 Roll…

It’s The Quadruple.

That’s right, you turn your sleeve over the cuff four times, resulting in a thick, sturdy roll that should definitely be above your elbow, even if you have longer sleeves.

The roll will be very thick, so take your time and avoid any twisting.

Be sure to go all the way around the roll.

This method isn’t for the faint of heart, so tread carefully. Make sure to keep each roll clean and crisp to avoid twisting and bunching, as this roll can get out of hand very easily.

If you mess up, feel free to reset and try again. Don’t force it because it will be uncomfortable all day long!

Consider a Short-Sleeve Dress Shirt

Folding up your dress shirt sleeves is only one way to beat the heat during the summer. An alternative idea is to wear a short-sleeve dress shirt. With a short-sleeve dress shirt, you won’t have to worry about rolling up the sleeves. Short-sleeve dress shirts only extend to about the elbows, so there’s no point in rolling up the sleeves any higher. Nonetheless, you can always wear a traditional long-sleeve dress shirt during the summer, as well as other times of the year. Just follow these steps to roll up the sleeves.

How to Roll Up T-Shirt Sleeves That Are Too Long