The Definitive Guide to Rolling Your Sleeves

We’ve all got long-sleeved shirts, and there’s just something less professional and manly about wearing a short-sleeved dress shirt as compared to rolling up your sleeves when necessary.  We’ll cover 3 ways to roll your sleeves, with some variants, and a couple pictures showing what we mean.

1) The Standard Roll:


Unless you want to look sloppy, you’re making sure that each roll is exactly the size of the cuff.  If you’re in the 1-2 roll range, you’ll look like the dude above, which is fine for more casual looks, or jeans even; when it falls in the middle of your forearm.


Roll up and have it end around your elbow, and you’ll be able to pull off more professional and fashionable looks.  This is generally in the 3 roll area, but it depends on your shirt, your cuffs, your forearms, and more.

Or, if you’re stylish, have fitted clothing, and are in shape, roll it above your elbow to show it off:


Just make sure you actually fold them over neatly based on cuff width, otherwise you can ruin an outfit like this dude:


This guy is doing pretty much everything correctly from the fit of his clothing to the color matching, but his sleeves make him look sloppy as shit (that and his poorly sized tie knot show his inattention to details).  Is he trying to look like a consummate professional deserving of a pay raise, or an entry-level accountant who tried to dress nicely for his first post-college job and is now taking a break from numbers he doesn’t understand while pondering his upcoming beer pong tournament?

At least he’s above Jim Kramer here though, who is clearly faking having his shit together:

tumblr_m69depeimg1r3wlbiNobody takes his financial advice seriously is what I’m saying, and is why he needs all those damned buzzers and blow horns to both keep your attention and distract him from his upcoming stress-induced heart attack.

But, there are other ways to roll your sleeves that aren’t as well-known.

2) The Master Roll

This goes down similarly to the Standard Roll and its variations, but is taken to another level.  First, pull your cuff over the sleeve to the desired length:


Next, roll the dangling sleeve in the same manner you would normally roll the cuff, keeping an eye out for the size of each roll.

You want to be able to end the sleeve roll so that a little bit of the top of the cuff sticks out, but while making sure the very bottom part of that final roll perfectly matches up with the bottom of the cuff.


It’ll take some practice and time at first, but I’m now able to do it just as easily as the Standard Roll.  Just keep in mind the size of each sleeve roll and how it’ll look when finished.

This roll looks particularly bad ass when you have a stylish shirt with cuffs that look differently from the rest of the sleeve:


3) The Casino Roll

This roll requires a special band or sleeve garter, and to know what I’m talking about, just think about a stereotypical casino dude with the black band.


The original intention was to be able to keep long sleeved shirts to end at a proper length, or to make long sleeves somewhat adjustable.  Although, now-a-days when people do wear them, it’s generally because they like how the band makes their arm stand out more than anything.


Be careful with this look though.  Much like the pocketwatch, it dances a fine line between being highly stylish, and seeming like you’re an unstylish role-player on their way to a Comic Con costume convention, or something.


And, those are the 3 main rolls, folks.  Here are some parting tips that apply regardless of how you roll:

  • Keep the rolls on each arm identical in length
  • Never scrunch roll
  • Rolled sleeves with a tie or bowtie is a no-no (and with a short sleeved shirt is a hell no-no)
  • Keep your sleeves and cuffs ironed, otherwise you’re drawing attention to your inattention to details with the wrinkles on full display

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4 thoughts on “The Definitive Guide to Rolling Your Sleeves

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