How to Roll Up Sleeves (6 Ways)

How to Roll Up Sleeves

So you’re trying to figure out how to roll your sleeves up properly.

You’ve arrived to the right place. Here, I’ll go over a couple various ways to roll up your sleeves, as well as some common blunders to avoid.

Perhaps it’s hot outside, and you’d like to give your arms a break. Perhaps you’re washing your mug in the office sink, or perhaps you just prefer the way your sleeves are rolled up.

Whatever the cause, you’ll want to roll up your sleeves properly. You want to avoid the dreaded sloppy roll at all costs.

Let’s speak about what not to do while we’re on the subject.

How Not To Roll Your Sleeves Up

The One and Done

First and foremost, you must avoid the one and done.

Simply unbutton your cuff, turn it once, and call it a day.

This looks to be unfinished and untidy. I’m amazed at how often I see this in public because it just looks sloppy to me.

The Pull Up

The pull up is a variation of the one and done, in which you perform the one and done and then pull the cuff up to your elbow, or above your elbow.

This looks sloppy again, and it doesn’t even remain in place when you move about.

I’ve heard this is known as the Italian roll, although I’ve never seen anyone doing it in Italy. As a result, I would avoid this strategy as well.

The Twist

You should also avoid the twist. This is where the cuff twists as you roll it, regardless of the method you use.

This not only doesn’t look good, but it also causes a tight roll around your arm.

As a result, it’s not particularly comfortable.

The Elbow Bender

Finally you want to ignore the elbow bender. This is a roll that is not quite below the elbow, not quite above the elbow, but right over the elbow joint. When you bend your elbow, the cuff folds in half, creating a large crease in the cuff.

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It’s not comfortable, and it becomes worse as the day goes on. It also doesn’t look good.

How To Roll Your Sleeves Up The Right Way

Let’s speak about how to roll your sleeves up the right manner now that we know what not to do.

I’m going to offer you six alternatives, and you can choose one or two of them as your go-to rolls based on your sleeve length, arm length, and personal preferences.

I’ll proceed from simple to complex in a logical order.

The Two Turn

The two turn is the first. It’s also known as the forearm hugger. This looks fantastic, especially on people with larger forearms.

Simply take your cuff, unbutton it, and roll it twice over itself. So you fold your cuff back and then fold your sleeve over the cuff.

It’s really simple to accomplish, and it’s also incredibly simple to undo. This is an excellent approach to use if you only need to roll your sleeves up fast, or if you’re washing something in the sink and don’t want to get them wet.

If you have slender arms, you can leave the second placket button buttoned, which will result in a tighter roll when using the two turn approach.

During the summer, this looks especially lovely on casual button-ups like Oxfords or linen shirts.

For dress shirts, I don’t think it’s the greatest method. If you’re going for a more formal style, avoid rolling your sleeves and instead opt for one of the above the elbow looks.

The J. Crew Roll – Below

Let’s talk about the J. Crew roll next. The Kennedy is another name for this. In fact, I believe John F. Kennedy popularized it. I’m not sure, but I’ve seen it referred to as the J. Crew roll.

This method leaves a small portion of your sleeve cuff protruding from the top of the roll. It looks to be quite cool.

This roll is fantastic because you can execute it either below or above the elbow.

You unbutton both buttons on your sleeve cuff and pull the cuff up about three quarters of the way up your forearm if you’re doing it below the elbow. Below the elbow, to be precise.

Then you fold the inside fabric over the cuff just enough to leave a sliver of the cuff sticking out the top.

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This gives the same basic turn as the two turn, but with a bit more visual interest. It’s a little more complicated, and it’s a little more difficult to accomplish, but it looks fantastic.

The J. Crew Roll – Above

You can also perform this with your arm over your elbow. It’s the same thing, except you’ll pull your cuff all the way up above your elbow when you unbutton it, and you’ll have more fabric to fold over the cuff. Just leave a little of the cuff’s top protruding.

This is a sturdily constructed roll. It remains in place throughout the day. It looks to be quite cool.

It will show a small sliver of contrast if you have contrasting cuffs.

It’ll take some practice to master this one. To ensure a nice and clean roll, you’ll want to get your fingers in there and make sure there’s no crazy folding or twisting going on.

Once you’ve mastered it, this could very well become your go-to approach because it looks great and is quite comfortable.

The J. Crew and a Half

If you have shorter arms and do the usual J. Crew roll, the roll may end up right on your elbow, which is something we don’t want.

What you can do is do the J. Crew and a half, as I like to call it.

Do the J. Crew roll above the elbow, then fold the cuff over itself. So you fold the entire cuff in half. This results in a shorter cuff, which looks nice on males who are lower in stature or have shorter arms.

It’s a tight roll that remains in place all day, is comfortable, and can eliminate the problem of the cuff being right over your elbow.

The Basic Roll

Next up we have the three turn or the basic roll.

Unlike the J. Crew roll, getting this one right doesn’t take a lot of practice. It’s most likely the strategy most males are employing right now.

You simply roll your cuff three times over itself. It’s the same as the two turn roll, but with an extra turn.

For this one, you’ll probably want to unbutton both buttons. If your arms are very slender, unbutton the cuff and keep the placket button secured for a tighter fit. However, most guys will want to unbutton both buttons.

This will most likely result in a roll above the elbow, but depending on the length of your arms and sleeves, it may result in a roll below the elbow, which is just OK.

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You can make one half turn if you do the three turn roll and it ends up right on your elbow, not below or above.

Turn the entire cuff, the entire roll, over itself once to cut it in half, just like the J. Crew and a half roll.

This makes it easier to get that roll above your elbow, as well as a thinner roll that looks excellent on shorter men.

The Quadruple

Finally, if you have really short arms or if your sleeves are a bit too long for your arms, you can utilize the quadruple sleeve rolling method, which is the granddaddy of all sleeve rolling methods.

You roll your sleeve four times over your cuff, creating a thick, durable roll that will stay in place all day. Even if you have shorter arms, it should be above your elbow.

This method is one of my favorites, especially if I just want my sleeves rolled up all day and above the elbow roll.

When you’re doing this, it’s critical to avoid twisting. Make sure to run your finger along the inside of the cuff after each turn to make sure there are no strange twists or folds. Because whatever mistakes you make on the first or second turn will be compounded on the third and fourth turns.

If you make a mistake, I recommend starting over since you don’t want to remain uncomfortable for the rest of the day.

That is all there is to it.

You now have six options. Any man should be able to find one or two that fit his needs. You’ll almost certainly need one procedure for below the elbow and another for above the elbow.

how to roll up dress shirt sleeves


  • Christopher

    Christopher has 9+ years of experience as a creative fashion designer who stays current with the latest trends.

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