How to Roll Up Sleeves: The Step-By-Step Guide

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You've probably never thought twice about how exactly you roll up your sleeves, but the way that you roll up your sleeves can actually make a big difference in how your shirt looks and fits. Furthermore, rolling your sleeves up properly will help you avoid the embarrassing sleeve drift when one sleeve is further up than the other.

As an added bonus, rolling your sleeves up in the right way can even make your arms appear more muscular. Who doesn't want that?

Here's what you need to know about how to roll up your sleeves in a way that will make you look great. Time to roll up your sleeves and get to work!

History Of Rolled Up Sleeves

Back in the olden days, men rolled up their sleeves in preparation of working with their hands, before landing a punch, or on their way to the bar. Watch a fight in an old western film and you'll be sure to see how carefully men rolled up their sleeves before throwing themselves into the brawl. 

In modern times, men may still roll up their sleeves for these reasons, but the long history of rolled sleeves has also evolved into a statement of style. Men roll up their sleeves to indicate a more relaxed attitude, to dress down a more formal outfit, and to show that they’re getting down to work.

Where To Stop Rolling

Should you roll your sleeves up above your elbow or below the elbow? Where below the elbow should you stop? The answer is a matter of personal preference. Some rolling techniques work better for different sleeve roll heights. 

As a general rule, shirts are rolled up above the elbow when you are about to do some physical work. This is because sleeves rolled up above the elbow are less likely to roll down in the midst of a lot of physical activity. Sleeves rolled up below the elbow are more often used to cool off a little bit or indicate the end of the day.

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How To Roll Up Your Sleeves

There's more than one way to roll up sleeves. Here are a couple of techniques that you can choose from to find the way that works best for you in each situation.

First Step For All Techniques

No matter what kind of technique you choose for rolling up your sleeves, the first step is to unbutton the gauntlet buttons at the shirt cuff and the gauntlet of the shirt.

  • The shirt cuff is the folded over fabric at the end of the sleeve at the hand. Generally there are two buttons here. 
  • The gauntlet is halfway up the sleeve opening on most shirts. The opening should be long enough to allow the sleeve to roll smoothly, which means that it needs a cuff button to hold it closed. 

1. Show Off Contrast Lining Or Design On The Inside Of The Cuff

If your dress shirt has contrasting lining or design inside the sleeves, this is the best technique for showing it off. If you intend to buy a shirt for the purpose of rolling up the sleeves most of the time, it's not a bad idea to choose a shirt that has contrasting lining or a design in order to make the most of your sleeve-rolling style.  

Contrasting sleeves can give you an opportunity to show off  your personal style and have some fun. For instance, the Twillory Non-Iron Skull Contrast Dress Shirt has a playful design of small skulls and dots on the inside to provide a very cool contrast when the sleeves are rolled up in this way. This shirt is also wrinkle free, so it'll look good when you unroll the sleeves as well. 

Here's how to roll up your sleeves in a way that will show off contrast lining:

  1. Roll sleeves up evenly about two widths of the cuff length
  2. Smooth creases or folds in the fabric and make sure the lines are even
  3. Roll from the bottom of the sleeve one more time to cover the cuff, but leave the very top exposed in order to show off the contrasting color or design

* when you want to unroll the sleeve again, just hold the top edge of the cuff and pull down

This is arguably the best way to roll up your sleeves, whether you have a contrasting interior or not. There are several advantages of this technique for rolling up the sleeve, aside from showing off the contrast lining: 

  • It is one of the least restrictive ways to roll up the sleeve, allowing the arm a free range of movement. If you have muscular arms and shirts tend to fit tightly, this may be the right pick for you.
  • Sleeves are firmly kept in place and won't tend to unroll until you are ready to unroll them, at which point it is very easy to do so
  • Looks neat whether you are showing off the contrast lining or not

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2. One Third Casual Roll

Not looking for anything complicated, but want to get your sleeves out of the way? The casual roll is the way to do it. This method of rolling up your sleeves will reveal only about one-third of your arm, just enough to get sleeves out of your way and free up hands while looking very attractive by following a couple simple rules. 

  1. Hold the bottom of the sleeve to about the width of the cuff
  2. Repeat a second time with the folded cuff, about the same width

* don't bother smoothing the fabric. You want this roll to look effortless and casual.

3. Basic Roll

When you were wearing your first dress shirt at 12 years old and you wanted to get the sleeves out of your way, this is probably the way you did it. It isn't the ideal method to use when rolling up your sleeves, since it is more time consuming than other tactics, restricts your arm movements, and is difficult to undo. Nevertheless, this is still a roll that some people prefer, so it is worth mentioning.

  1. Fold the sleeve once, using the cuff as a measuring point
  2. Continue to repeat this movement until you reach the desired height, generally past the elbow, tugging at the fabric as you go to keep it straight and smooth 

* This technique works best when your shirt sleeves are much wider than your arms, as the extra fabric is needed in order to continue rolling. Some shirts designed with wide sleeves have a button or strip of fabric on the inside of the sleeve to secure the roll 

4. Show Off Your Arms

Are your arms worth showing off? If you've got big biceps or tattoos that you want to put on display, this technique will be perfect for you, since it lets you roll sleeves up well past your elbow while still allowing plenty of free movement. 

It's also a great technique when you have some meaningful manual labor to do. It is best to use a shirt that has relatively wide arms in order to allow enough room for this technique.

  1. Utilize this technique before putting your shirt on
  2. Lay your shirt down on a flat surface
  3. Fold your sleeves a cuff width
  4. Fold another cuff with, covering the folded part of the shirt's cuff 
  5. Fold a third and a fourth time until you reach the desired length 

How To Use A Sleeve Garter or Clip

In the 1960s, waiters found a solution to shirtsleeves that lose elasticity and tend to unroll. They used a band, known as a sleeve garter, to hold a folded sleeve firmly in place. This technique is still useful, especially for older or looser shirts or people who are very active. It is favored by soccer player David Beckham. 

Most sleeve garters are elastic, but you can also find silk or metal garters and even choose garters with patterns or contrasting colors. In a pinch, a strong rubber band can also be used. Keep that in mind when you are desperate to keep your sleeves up on an especially busy day at the office. 

Roll your sleeves up and use the sleeve garter to hold them in place. Leave the garters exposed if they are decorative or cover them with a few inches of sleeve if you would rather keep them hidden.

Shirt arm clips are a more elegant alternative to garters. They look just like a tie clip and can be used by rolling your sleeves up and then clipping them in place with the clip arm facing out. 

Roll Up Your Sleeves With Style

Long sleeves are the standard for dress shirts, but there will doubtless be times when you would rather roll your sleeves up. Rolling up your sleeves can make a button up shirt seem like a more casual shirt for when you want to get a drink after work and it is considerably cooler to wear your sleeves rolled up.

If you're dressing for a formal occasion on a hot day, rolled up sleeves can have a more formal effect than simply wearing short sleeves, even if you never roll the sleeves down.

Be sure to choose high quality dress shirts when planning to roll up your sleeves. Twillory Wrinkle-Free Dress Shirts are perfect for when you want to be able to roll your sleeves up and down throughout the day without turning into a wrinkly mess. 

Practice a few techniques and you’re sure to find one that works best for your body type, shirts, and personal style!


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Twillory