Roll Your Sleeves Right For Your Dress Shirt


Oftentimes, when looking around at a workplace where smart attire is the norm, you would find a smattering of the male employees with their sleeves rolled up to varying degrees. This would raise two questions – one would be why do they roll up their sleeves and the other would be whether there is an art to rolling up the sleeve.

In this post, we attempt to answer both these questions.

There are 3 main reasons for wanting to roll up your sleeves when wearing a dress shirt.

1. NecessityWashing Hands Requires Rolling Up Your Sleeve

The first reason is if you absolutely needed to. An example would be while washing your hands or you may also roll up your sleeves for any ‘dirty work’ that arises at the job from time to time, such as having to do some heavy lifting.


2. WeatherRolling Up Sleeves Required Due To Hot Weather

Some days, the heat and temperature gets to you, especially if you’re just stepping into the office from outside or worse – if your office does not have air-conditioning. You may even be in a crowded meeting room, where despite the air-con, the bodies around you cause you to get heated up. One of the easiest way to cool off would be by rolling up your sleeves.

Wanting a Casual Style at Work May Cause You To Roll Up your Sleeves

3. Style

It could also be that you just wish to sport a casual look at work on some days – and with a smart attire requirement at the office, the only way to add some casual style is by messing with your sleeves.




Now that we have discussed the whys – let’s take a look at the 3 distinctive sleeve rolls that are commonly used by men.

The Simple Roll for your Dress Shirt SleeveThe Simple Roll

This is the go-to for most men, and is sometimes also known as the Basic or the Classic Roll. This is due to its simplicity – where you fold the sleeves of your dress shirt back once or twice the length of the cuff, and that’s it. The sleeve still stays below the elbow and affords breathing room for the wearer.

The Simple Roll gives the wearer a slightly casual look, and can be used at work.

The Hard Work Roll for your Dress Shirt SleeveThe Hard Work Roll

The Hard Work Roll is a follow on to the Simple Roll as it involves continuing to roll the sleeve back until the sleeve is ABOVE the elbow. This could be 3 to 4 rolls depending on the cuff length. This sleeve roll can be brought out when there is a need for heavy lifting or hard work involved – hence its name.

Normally, after a long day at the office, you may choose to bring out this sleeve roll as well. This is a much more casual look and is also spotted in use often during after-work drinks.

The Inside Out Roll for your Dress Shirt SleevesThe Inside Out Roll

The Inside Out Roll is one where the first fold is considerably larger when you turn your cuff inside out and pull it back a couple of cuff lengths before starting to roll from the bottom of the inside out sleeve to the top of the cuff. You can choose to show some of the cuff at the top, especially if the cuff is off a contrasting color.

Due to the nature of its folding, the Inside Out Roll is considered a more stylish look and also casual – perfect for use when heading out or after work.


A factor to consider when deciding whether to roll up the sleeves on your dress shirt is whether your body type is right for the shirt you are wearing. If you are wearing a baggy dress shirt, your sleeve will tend to flap more when rolled up and would generally look bad and if you have skinny arms, you want to ensure that your dress shirt fits well. Also be mindful that these styles do not apply to french cuffs, which are much more formal in nature. In the rare case that you decide to roll up sleeves on a french cuff shirt, the best style to utilize is the Simple Roll.

Here is an infographic that shows you how to fold your sleeves correctly to achieve these looks.

Rolling your dress shirt sleeves infographic by Hucklebury


Are there any other ways that you roll up your sleeves that we did not cover here? We would love to find out so leave us a comment!


Credit: Feature image contains images from BlackLapel.

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About Author

Dhawal Shah

Through Art of Style Club, Dhawal Shah is educating himself on lifestyle matters affecting everyday men and bringing a fresh perspective to answer their questions. He is also the co-founder of 2Stallions Digital Marketing Agency, and an expert on web development, SEO, SEM, Marketing Automation & Social Media.

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