Dress Shirt Sleeve


How to Roll Up Your Shirt Sleeves

Is it blistering hot outside or have you had a long day or do you just want to show off your forearms? Just roll your sleeves up and that’s that, right? Not really. There are some proper ways to roll your sleeves to keep you looking classy and stylish.

Rolling up your sleeves has become more and more acceptable nowadays as offices around the world have become more casual. So it’s best to know how to do it, and we’re here to help.

Man Dress Shirt

When to Roll Your Sleeves

Before we talk about how to roll your sleeves up, it’s important to know when to do it. Also, we’re going to focus on rolling up the sleeves of long sleeve dress shirts, not short sleeve dress shirts or T-shirts or polos or even flannel, though these methods are relevant for those. These are more casual and don’t really have too many rules. Just roll them up a couple times, and only do it if the sleeves aren’t super tight already and if you have the confidence to have your short sleeves be even higher up on your bicep.

Now on to the important stuff. Rolling up your sleeves is undeniably casual. It has become a stylish way to stand out and show you don’t care about rules, but in normal life settings, there are times to do it and times not to.

The first reason and how rolling sleeves actually became a thing is for practicality. Way back in the day men only used to roll up their sleeves when they had to, so their nice shirt didn’t get dirty when doing dirty work. And this is still probably the most valid reason to do so. If you are going to do some manual labor like fixing a toilet or doing the dishes, roll your sleeves up. The other end of practical reasons are things such as washing your hands or eating a meal.

The next most common reason to roll your sleeves up is also a practical one and simple. If it’s hot outside, you can roll your sleeves up. We are men, we sweat when it gets hot, and sometimes we need to cool down a little. So rolling your sleeves up is a way to do that. This reason is simple and obvious, though some men heat up faster than others, so timing may vary.

The last and increasingly popular reason to roll your sleeves is if you are in a casual or personal environment. This situation has a few rules. The easiest to follow and remember is if you are alone in the office doing work, if you are at your house and want to relax, or if you are done for the day and are going to a bar or pub with some friends after work.

Men's Shirt Sleeve

Those rules are basically common sense, but nowadays many offices have become more casual. The simplest way to know if your office or office situation is casual is if other men or managers have their sleeves rolled up. This can be during normal daily routines or during casual meetings. Just follow the atmosphere and fellow employees to know if it’s appropriate to roll up your sleeves. For presentations or when meeting clients or higher managers, it’s best to always keep your sleeves down and buttoned and tidy. Now onto the rolling methods.

Casual Roll

This is the simplest and quickest method. It can also often be the coolest as you still get forearm breathing and the ends of the sleeves are often looser than other methods so you get more airflow to the rest of your arm. It is also, as the name suggests, the most casual roll by far. So only use this roll for practical reasons like eating or washing your hands or when alone in the office doing work. It is easy to unroll and will have the least chance of wrinkling when unrolled.

To complete this roll, you must unbutton both cuff and gauntlet buttons, then fold the cuff back so it’s inside out and set back on the sleeve. Then simply fold over one more time the exact length of the cuff, tuck the exposed corners in, and you’re done.

Folded Shirts

Basic Roll

This roll is also called the classic roll. It is also the most intuitive roll and how most men know how to do it. The basic roll will create the tightest sleeves for your shirt, so if it is already a tight shirt, don’t opt for this method. It is also the most secure roll and the one that will definitely leave the most wrinkles when unrolled. For these reasons, this roll is the method for when doing manual labor or you simply prefer it.

The basic roll starts exactly the same as the casual roll. Unbutton both buttons and fold the cuff back. Fold the sleeve back over the cuff, using the cuff as a guide for how wide each fold should be, as many times as needed for the sleeve to end just below the elbow. If you are doing work that could go up to your elbows, roll the sleeves a few lengths higher so it’s above your elbow.

Italian Roll

This roll is also known as the master roll. It is the classiest and most stylish roll by far in our opinion. It looks great, doesn’t wrinkle too much, and is very easy to adjust. We therefore recommend this roll for all things except difficult or messy manual labor. Whether in a casual office setting or going out for drinks, the Italian method is the way to go.

This roll is different than the other two, though it still starts by unbuttoning both cuff and gauntlet buttons. Now fold the cuff back just like the others, then you pull the cuff up your arm so the end of the inside-out cuff lines up with your elbow crease. The next and final step is to fold the bottom of the remaining sleeve up and over the cuff so it’s trapped and steady on your arm. You can leave the top of the cuff exposed as much as you like for length or style, as some shirts have different colored inside portions of the cuffs so it can look cool if a little is exposed.

All three of these methods can be better understood with a little visual aid. Click here for just that.

Men's Dress Shirts

General Things to Remember

The first and most important thing to remember is when to roll up your sleeves. If you are doing labor or it’s excessively hot outside, roll them up. If your office environment is casual or a certain situation is casual, go ahead and roll them up. If you are meeting clients or in important meetings, keep the sleeves down and more professional.

Always remember to unbutton both the cuff button and gauntlet button. The cuff button must be undone for a sleeve roll to even be possible. And the gauntlet button must be undone when rolling a sleeve or the sleeve will suffocate your arm.

Never roll your sleeve above your elbow unless doing labor that requires so. It looks tackier and out of touch than a sleeve rolled just below the elbow. So keep it at that length to stay looking good.

You generally don’t want to roll your sleeves when wearing a tie, unless it’s for a temporary amount of time. If it’s your all day look or if it’s with a white shirt, you will tend to look like a politician which isn’t always desirable these days. This can look okay if you are going for a very casual hipster look, but these aren’t the situations we’re talking about here.

You should also never roll up your sleeves when wearing just a vest. This will make you look out of touch or like a bartender. If you’re not a bartender or the vest isn’t part of a uniform, don’t roll up the sleeves with just a vest.

Don’t ever keep your sleeves rolled up under a jacket. This should seem obvious but it isn’t always. If the jacket is on, the sleeves are down. Simple.

Always roll each sleeve to the same length as the other. Otherwise, it just looks sloppy. Keep them even, fellas.

Lastly, to avoid wrinkles, the first step is to carefully fold your sleeves rather than actually roll them, despite the term “roll up your sleeves.” Also, never leave your sleeves rolled up longer than necessary or planned. You will have fewer wrinkles when the shirt is unrolled to its original length.

Folded Dress Shirts


Rolling your sleeves can be necessary sometimes. Whether to keep them from getting dirty or if it’s hot outside, you can roll them up. And if your office is more casual or if you’re going out after work, roll up those sleeves if you want to present a more relaxed look. Just always remember to follow a few simple rules to keep from looking sloppy or out of place.