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Style hack: How to cuff your shirtsleeves like a pro

Follow this guideline to look masculine

how to cuff sleeves man in rolled
Aravind Kowtharapu / Pexels

In the undoubtedly long list of times you have laid in bed or on the couch, mindlessly scrolling TikTok or Instagram, you have likely come across the innumerable posts, reels, or videos where women list out some of the sexiest things a man can do. You would expect some things: chopping wood, standing between them and danger, or being a good father. Some others are interestingly insignificant in the grand scheme of things and something we all do in our everyday lives without even thinking. Putting your hand on the passenger seat to turn around and back up the vehicle. Placing your hand in just the right place to keep them from hitting their heads. And one of the most often uttered is when a man rolls up his sleeves. Of course, this is just one of many style hacks you can use, and learning how to cuff sleeves is vital to your look. Here is how and why to get it right.

Relaxed and manly style

Man rolling his sleeves
The Manual

Why roll up your sleeves? Why take a shirt that was made as a long sleeve and turn it into a short-sleeved shirt? You never see us turning a short-sleeved shirt into a long-sleeved sleeve. Well, first of all, if we could do that, we probably would. But the main reason for doing it is to function. You can’t control the weather. Sometimes, it will catch you off guard, and you simply aren’t expecting the temperature to rise as it sometimes can. Rolling your sleeves is a great way to roll (pun intended) with the weather the way you do when you layer. It just doesn’t require as much preparation.

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The second reason is the psychological effect it has. There is something effortlessly sexy and masculine when you roll your sleeves. Whether you are in a dress shirt and dress pants or a flannel and jeans, rolling your sleeves will add a layer of casual attitude to the look. On top of simply looking masculine, there is the image of a man ready to get things done. There is even a saying, “roll up your sleeves and get to it.” When you are prepared to be masculine and effectively hardworking, flip your sleeves up and finish it. But, like everything else, there is a method to this style hack.

The cuff method

Man with sleeves cuffed
Luis Alberto Cardenas Otaya / Pexels

The first thing we should get straight here is that there is a huge difference between rolling your sleeves and cuffing them. Rolling them consists of multiple folds that shorten the sleeve up your arm near the elbows. Cuffing the sleeves consists of one fold that flips the cuff of your shirt inside out and reveals the wrists. This method can be excellent when you have a stellar watch you want to show off. There are a few different things to keep in mind when choosing this method:

  • This is best done with dress shirts. While casual shirts look great like this, the structure of a dress shirt offers some stiffness that keeps the sleeves in place. A casual shirt’s collars will have a more challenging time staying cuffed.
  • This look is a design intent for some shirts. If you have ever watched Modern Family, you have seen Cam utilize this look repeatedly. Many high-end dress shirts have contrasting collars and cuffs. The underside of the cuff is a brighter color or pattern, perfect for cuffing to show off a little personality. Just remember that this can definitely be done too much, and it looks garish.
  • Finally, if you are wearing a dress shirt under a sweater, this is a look that gives it depth. Cuff the sleeve outside the sweater for a more casual alternative to the dressy sweater over a dress shirt look.

The rule of three

Man in overshirt
The Manual

Finally, the method that most of the original posters on social media are talking about when they reference this style hack is rolling the sleeves. While cuffing the sleeve is simply one fold of the sleeve, rolling requires multiple folds of the sleeves that reveal the whole of the forearm. The rule of thumb here, to avoid it landing awkwardly on the forearm or going too high on the bicep, is to stick to three folds of the sleeve at the same width of the cuff. With the cuff having a seam at the edge, there is a natural place where it is easier to fold the cuff back. After three folds, this sleeve should sit just under your elbow. Here are some things to keep in mind when using this method.

  • When rolling the cuff of a casual shirt, ensure that you don’t keep them rolled between wears. This can cause pesky wrinkles that are difficult to remove.
  • When wearing a henley or long-sleeve tee under a casual button-up, feel free to keep the sleeves at the wrist while rolling the cuffed sleeves up. This adds some dimension to your casual outfit.
  • Finally, don’t be shy when rolling sleeves with the henley, too, while wearing it by itself. Sometimes, henleys don’t have elastic cuffs and don’t stay in place when pushed up. So, when wearing a henley, the effect will be the same if you want to use this same method to roll the sleeves.
Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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