The Art of the Rolled Sleeve


Long sleeves add a swagger to your outfit that you just can’t accomplish with short ones—they’re stylish, flattering and are able to transition well between casual and formal events. We wear them for a variety of reasons, but regardless of why you’ve chosen to complete your look with a long sleeved shirt, every man shares a common occurrence—at some point, you need to roll up your sleeves!

It’s a very natural process, rolling your sleeves, which we don’t put much thought in to. However, rolling your sleeves can indicate many things. For instance, you may want a more relaxed appearance after work while you meet the guys for a drink at the bar. Things may get out of hand at the bar and the only indication some asshole gets prior to you decking him in the face, is the visual of rolling up your sleeves (cautious of ruining any fabric). Or, after the bar, you may need to roll them one more time to fix the sink your spouse has been nagging you about for two weeks. When situations come up—so should your sleeves.

Now, let’s be clear that rolling your sleeves does serve multiple purposes, but it also has evolved into a fashion trend, which means there is a correct and incorrect way of doing things— so pay attention!

For starters, it’s a casual look, so even though you can still look good, avoid doing this in any formal or office setting. Only do so when it’s practical or prior to doing something that could potentially damage or dirty your fabric. Next, when I say “roll” your sleeve, I’m referring to folding them. Folding will give anyone a cleaner look and will ensure that the sleeves will look good once they are rolled back down by preventing wrinkles. Lastly, make sure you undo any buttons or remove any cufflinks prior to rolling your sleeves. Make sure the sleeve is rolled up to the forearm or just above the elbow.


Read through some samples below on how to role your sleeves based on the look you want to accomplish.

The Quickie:

The name says it all! This roll is casual and should only be utilized swiftly during brief moments throughout the day—like washing your hands or eating on the go between office meetings. This fold is temporary and not recommended for long periods of time.

               1. Make sure all of the buttons on your sleeve are undone.

               2.  Turn the cuff up just under your elbow.

               3. Fold the edge of the cuff by flipping it down into the cuff so that it’s tucked                in.

               4. Roll the sleeve up by flipping/folding it over itself.

Plain and Simple:

This roll is the most frequently used because it’s arguably the easiest.  You don’t need expert knowledge on where to fold; the length of the cuff determines the length of the role.

               1. Unbutton the cuff and roll it up 2-3 times.

               2. After each roll, flatten the fabric completely before rolling the next.

               3. Make sure that each sleeve is evenly rolled.

Business Casual:

When you’re meeting your boys after a long day at the office, this is the perfect look that says you’re ready to relax. You can still look professional, but you are able to get a little more comfort and airflow.

               1. Fold the unbuttoned cuff back 1-2 times over itself (don’t go past your elbow)

               2. Same as the “Plain and Simple”, make sure the folds are done evenly and                flattened before the next.

               3. Adjust until you feel comfortable and look damn good


What’s better than comfort and swagger? Nothing (pertaining to fashion). This casual role leaves a little more room for movement and gives your sleeve game an advantage over others.

               1. Fold the unbuttoned cuff backwards. Pull it up your arms until it is slightly              longer than where you want the roll to end on your arm.

               2. Take the part of the sleeve under the cuff and fold it up, towards the cuff                (make sure the roll is the same length all the way around and flat)

               3. Adjust until you are content with the amount of cuff showing.

The Italian:


This method is proof that the minor detailing can significantly enhance your look. This roll looks excellent with dress shirts that have contrasting fabric inside the cuff.

When the contrasting fabric is exposed, the effortless look is highly admired.

               1. Unbutton the shirt’s cuff and fold it so the cuff is roughly an inch past your     elbow (you’re only folding it once, so it should be a long fold).

               2. Flip the bottom of your sleeve closest to your hand over so it creates                another fold and shortens the length of the rolled cuff. Make sure that you only      roll about an inch less than the first roll. This allows about an inch of the                sleeve’s cuff to poke past the fold, adding layer and dimension.


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