Looking for the best way to roll up your sleeves? Try one of these seven time-tested methods.
Whether you’re wearing a dress shirt or a casual button up shirt (a.k.a., a button down), you’re probably going to roll your sleeves up every so often.
- Maybe it’s hot outside, and you need to let your arms breath.
- Maybe you’re washing your mug out in the office sink and don’t want to get your sleeves wet.
- Maybe your sleeves are too long.
- Or maybe you just like the casual vibe that rolled sleeves produce.
No matter the reason, you want to roll your sleeves the right way, or at least avoid the dreaded “sloppy roll”.
So what’s the best way to roll your sleeves up? Should you go below the elbow or above? Should you unbutton the placket or leave it fastened?
And what the heck is the “j crew roll” anyway?
Here’s everything you need to know. Oh, and if you’re wondering, the Oxford shirt I’m wearing in these pics is from Ash & Erie.
Table of Contents
How NOT to Roll Your Sleeves Up
Like many things in fashion, if you just avoid mistakes, you’ll look better than 90% of other people. Here’s how not to roll your sleeves:
The One and Done
This is where you just cuff your sleeves once and forget about it.
It looks unfinished and sloppy, and I’m kind of surprised how often I still see this sleeve roll method out in the wild.
The Pull Up
This is like the one and done, but you pull the cuff all the way up to your elbow.
I’ve seen this called sprezzatura, but to me, it just looks sloppy.
No matter which method you’re using, sometimes it gets twisted up during the rolling process.
This tends to tighten your sleeve, which is uncomfortable, and it looks a bit unkempt.
The Elbow Bender
This is where indecision causes your cuff to land right over your elbow. Is it an above the elbow roll or below the elbow?
It makes it hard to bend your arm and causes a big crease in the cuff throughout the day. Not a great look.
7 Ways to Roll Your Shirt Sleeves Up
Now that we know what not to do, let’s talk about the right way to roll (FYI, these methods are listed in a logical order of increasing complexity).
The Two Turn (a.k.a., Forearm Hugger)
In general, I think many guys look better with above-the-elbow rolls, but this method is great for a few reasons:
- Super quick
- Easy to undo
- Causes less wrinkling
Here’s how to do it:
It looks great on guys with big forearms, but if you have thin forearms, just leave the placket button fastened, as this will ensure the sleeve squeezes your arm a bit.
This method is also great for more looser fitting shirts (think casual linen button ups during summer).
That said, if you’re wearing a dress shirt, and the sleeves are a bit too loose around your arms, the Two Turn isn’t a good option.
Instead, go for one of the above-the-elbow techniques toward the end of this list.
The Mini J. Crew Roll (a.k.a., The Forearm Kennedy)
This is still a below the elbow method, and it produces similar results to The Two Turn, but the technique is slightly different.
I like this roll because it’s slightly more visually interesting than the Two Turn, but it does take a little practice to get it right.
Keep in mind, if your shirt fabric is a different color on the inside, this method will expose that contrast, which isn’t always desirable.
The J. Crew Roll
Popularized by JFK but somehow named after J. Crew, this is arguably the best way to roll up your sleeves.
It’s quick, clean and stays put all day. Plus, it adds a bit of visual interest by letting your shirt cuff poke out a bit.
It’s like The Kennedy (or Mini J. Crew), just above the elbow. Here’s how you do it:
When in doubt, go with the J. Crew Roll (a.k.a., The Kennedy) for an above the elbow roll.
It looks good on everyone, it’s easy to do after some practice, and it stays in place nicely.
The J. Crew and a Half
If you have shorter arms, the standard J. Crew roll might leave the roll right at your elbow, which we know is problematic.
To shorten the sleeve a little further, fold the entire roll in half once. You’ll still have the cuff poking out a bit, so you’ll still have that signature look.
The added benefit of this technique is that it creates a thinner roll, which looks more proportionate on smaller guys.
As a short, thin man, this is how I usually roll my shirt sleeves up if I’m going for an above the elbow look.
The “Basic” Roll (a.k.a., the Three Turn)
Unlike the J. Crew Rolls, this basic roll doesn’t take much practice to get right.
You simply unbutton your cuff and roll your sleeve over itself three times. Here are the details:
Depending how long your arms and sleeves are, this will likely result in an above the elbow roll that stays in place all day.
If your sleeves are a bit longer, this may result in a below the elbow roll, which is okay too.
However, if you’re not happy with where the roll ended up on your arm (i.e., it’s right over your elbow), you have a couple more options
The 3.5 Roll
Just like the J. Crew and a Half, this roll is great for guys with shorter arms, as it produces a shorter cuff.
You do the Three Turn Roll shown above, then fold the entire cuff in half once.
As a shorter guy, I like to use this method to ensure the roll clears my elbow. I also like the mini cuff it produces.
The Quadruple (a.k.a., El Cuadruplicar)
Finally, if you have very short arms or very long sleeves, you may need to use the mack daddy of all sleeve rolling methods.
It’s not the Three Turn, it’s not the 3.5 Roll…
It’s The Quadruple.
That’s right, you turn your sleeve over the cuff four times, resulting in a thick, sturdy roll that should definitely be above your elbow, even if you have longer sleeves.
This method isn’t for the faint of heart, so tread carefully. Make sure to keep each roll clean and crisp to avoid twisting and bunching, as this roll can get out of hand very easily.
If you mess up, feel free to reset and try again. Don’t force it because it will be uncomfortable all day long!
How do you roll (your sleeves)?
Between these seven different sleeve rolling methods, any guy should be able to find one or two that works perfectly for his build and aesthetic.
Don’t be afraid to experiment with multiple techniques, as it’s a good idea to have at least two in your arsenal (one below the elbow and one above the elbow).