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How to Roll Up Your Sleeves For Men | Quick Shirt Styling Tips

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Did you know that there is an appropriate time to roll up your sleeves when you’re wearing a button up? Sometimes it may just feel natural to roll up your sleeves when you’re working, but it’s not always the case in every situation. You may be carrying out poor etiquette!

Luckily, not everyone knows about the ins and outs of sleeve rolling. Here, we’ll go over and how and when is the best time to roll up your shirt sleeves. Maintaining your composure and posture is important, just like how you wear your clothes. Way back in the day, it was indecent to roll up your sleeves at all because presenting and dressing yourself properly meant you shouldn’t tamper with your clothes in any way. It’s meant to be displayed as how it was made, so it would be sloppy or messy when you would roll up your sleeve. Furthermore, people would keep their jackets on until you got home and you were off work, so you wouldn’t even get an opportunity to touch your shirt sleeves!

Now we’ve come to a point in our society where it’s okay to be casual at times in the office and rolling up your sleeves is a great sign to express that. Rolling up your shirt sleeves can make a big commotion, so let’s take a look at when is the best time to.

roll up sleeves man wearing white shirt

When is the right time to roll up my sleeves?

First off, is there a right and wrong time to roll up your sleeves? Definitely! It’s not just a question of being comfortable, but of professionalism as well. In a work environment, perhaps when talking with your superiors, boss, or in a business meeting with clients, you wouldn’t roll up your sleeves because rolling up your sleeves is a way to express casualness. There’s a right and wrong time to be casual in front of your boss right? Let’s peep at a couple of reasons why you’d roll up your sleeves.

When the weather is unbearably hot outside

When the weather is hot and stuff and you’re not able to have access to air conditioning, it would be a good time to roll up your sleeves. This will provide more airflow through your arms so you wouldn’t produce as much sweat. This is also good if you’re directly in contact with sunlight, especially in outdoor conditions.

When you’re working with your hands

What about when you’re working? Well this depends on the type of work that you do. If you’re doing some physical labor, then it would be appropriate to roll up your sleeves. Lifting boxes, moving heavy objects, etc. these should enable you to roll up your sleeves. This can coincide with earlier about the temperature of your workplace since it might not depend on the type of work that you do, but more so if it starts feeling extremely warm.

Avoiding getting your sleeves dirty or wet is another great reason why you should roll up your sleeves. Perhaps you might be changing the ink in the printer, grabbing files from a dusty cabinet or box, or simply grabbing food for lunch, you’re going to want to roll the sleeves up to avoid them getting stained. When you’re out, dirty sleeves are a hassle to clean, especially when you’re going to be constantly meeting with clients or in meetings all day. You’d need to be prepared with cleaning supplies or a spare shirt to save yourself! Also, when you’re washing your hands is a good time to get your sleeves rolled up as well!

When you’re on the go 

While you’re traveling or commuting is another scenario where you’d roll up your sleeves. There shouldn’t be a need for you to be professionally dressed unless you constantly have to travel with or to meet clients. Also entering casual environments such as happy hour after work, dinner parties, etc. Any casual meeting would be the time to roll up your sleeves! You don’t want to be giving off a stern attitude when everyone is loosening up right? When you’re at a casual event, it’s good to be and show that you’re relaxed because it’s not only good for you as an individual to not be stressed anymore, but it helps others around you to feel comfortable. 

man rolling up sleeves in office

Different sleeve roll-up methods

That said, there are also several different ways to roll up your sleeves. Even though it’s a simple act, the details in fashion matter. Here are a couple different ways you can experiment with your button ups. 

The Quick Roll

  1. Unbutton only the wrist button, not the gauntlet button.
  2. Fold at the seam of the cuff and the sleeve.
  3. Fold once more to cover the cuff.

The Casual Roll

  1. Unbutton the cuff and gauntlet buttons.
  2. Flip the cuff over. Make sure it is straight and flat for both the top and bottom.
  3. Proceed to fold. Your cuff will indicate the width of the roll, and you’d tuck the cuff into the roll, fully covering it.
  4. Repeat the folds until you reach your desired height. (just pass your elbow tip or right below it (covering your elbow still))

The Italian Roll (GQ Roll)

  1. Have both buttons undone.
  2. Fold the sleeve up so that the entire cuff is around one inch above your elbow.
  3. Then roll the sleeve up on top of the cuff, which you would need to sort of tuck your sleeve into the roll, but allow perhaps ⅓ of the cuff to still be exposed.

The Master Sleeve Roll

  1. Unbutton both buttons.
  2. Flip the cuffs and pull it about two cuff lengths up or until just below your elbow without folding.
    1. Smooth any creases or folds in the fabric
  3. Now roll from the bottom end of the sleeve to cover the cuff, but leave the very top end of the cuff exposed.
    1. If the cuff has a different print or design, this is where you leave a hint of it showing.

The AIFA Roll

  1. Unbutton the buttons.
  2. Fold the bottom of the sleeve once, which should be the width of your cuff.
  3. Repeat once more with the same width of your cuff.
  4. Avoiding smoothing the fabric as this is intended to look very casual and effortless.
    1. This roll follow’s the design principle of the thirds where you only show ⅓ of your arm.

Tips For Your Sleeves

Whenever you roll up your sleeves, there’s definitely a few guidelines to follow that can apply to most, if not all of the sleeve roll ups. When you’re trying to show the best etiquette, it’s best to follow through and don’t miss any details or you will find that not only may you be disappointing your audience and who you represent, but also embarrassing yourself! Here are some general tips about your shirt sleeves!

  • Definitely launder, wash, and iron your shirt before you wear it out!
  • Keep your elbows inside of your shirt sleeves when rolling up unless you fall into these categories or similar situations:
    • You will be performing some physical labor
    • You’re afraid sleeves will get dirty from whatever you may be doing
  • Roll your shirt sleeves evenly: not one higher or shorter than the other.
  • It is best practice to be folding your shirt sleeves as you roll them. This will minimize the chance that your sleeves will wrinkle and look less sloppy, resulting in a more polished, fresh style.
  • Please remember to remove any buttons and cufflinks before you roll up your shirt sleeves. Not only will they prove to be obstacles during your rolling, but they might ruin your sleeves and cause wrinkles as well.
  • Don’t leave your shirt sleeves rolled and folded if you’re putting on a jacket, vest, or any sort of outerwear on top.
    • Suit or sport jackets are usually pushed up, not rolled unless it’s immediate and it proves to be of practical need
    • The rolled sleeves will leave a bulky presence on your arms if you leave them rolled, so it’s not a pleasant look.
    • If you want to roll up your sleeves, take your jacket off! 
  • Don’t ever fold your cuffs when rolling your sleeves, especially when your cuffs are stiff because this will ruin the cuffs forever!
  • Avoid rolling up sleeves when you’re wearing a tie.
    • Wearing a tie is more formal and rolling sleeves is casual, so it’s contradicting when both of these elements are in place, unless you’re planning to loosen your tie as well!

In addition, here are a few things to keep in mind to prevent further or permanent wrinkles on your shirt sleeves!

  • Never keep your shirt sleeves rolled up longer than necessary. Unroll them as soon as you no longer need them rolled.
  • Don’t leave buttons fastened or cufflinks attached when rolling sleeves
  • Make sure to fold the sleeves when rolling to make sure it’s neat and not creased or bulging.
    • Exceptions are the methods of rolling that do not require you to fold so it’s a more relaxed look. For example the AIFA roll.
  • Never hang or launder a shirt that still has sleeves rolled up. Unroll them!

We know some things may have been repeated, but it doesn’t hurt to go over important details a second time especially if it may affect not just the quality of your rolling technique, but to preserve the quality of your shirt as well.


Life isn’t as simple as you thought it was anymore right? Rolling up your shirt sleeves definitely makes an impression on others and it’s crucial especially when you’re in a working professional environment or if you’re in a leadership role, there’s a right and wrong time to be having your sleeves rolled! We, as a society, have learned that keeping things too strict will exhaust your employees and cause more of a negative impact than just your appearance, so it is good to learn about rolled up sleeves for a more relaxed presence at the appropriate time. That said, you may not be wearing a dress shirt in some of the scenarios listed above, but a flannel would definitely still be work appropriate and look great with rolled up sleeves. Check out Nimble’s collection of flannels for more casual workwear options. 

Rolling up your shirt sleeves is definitely a combination of style and comfort. With this information in mind, you should experiment and find the best technique for you! Some last notes before you go are that some of these rolls may come loose more easily compared to others and this can be any number of reasons from your arm size, shirt sleeve length, or the material of your shirt. Don’t just be limited in one way to roll up your sleeves. Having balance in both style and comfort is a great way to be dressed perfectly for any and every occasion.