7 Ways to Roll Your Shirt Sleeves Up (Visual Guide) (Visual Guide)

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.

Italian roll — Trust me, they ain’t doing this in Italy 😏

I’ve seen this called sprezzatura, but to me, it just looks sloppy.

The Twist

No matter which method you’re using, sometimes it gets twisted up during the rolling process.

Twisted sleeves — This is the sloppy joe of sleeve rolls.

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?

Who knows?!

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:

Unbuttoned cuff — Start with sleeves unbuttoned (both buttons, if there are two).

Two turn 1 — Fold the cuff back over itself once.

Two turn 2 — Fold the cuff over itself one more time.

Two turn 3 — Make sure it’s folded cleanly, all the way around (no twisting).

Two turn 4 — Pull down lightly to finish.

Two turn sleeve roll looser front — …and you’re done!

Two turn sleeve roll looser arms bent — Laid back, casual, comfortable.

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.

Two turn sleeve roll tighter — If you want your sleeve to grab your forearm, button the second sleeve placket button (if your shirt has one).

Two turn sleeve roll tighter arms bent — This is my go-to sleeve rolling method 80% of the time.

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.

Forearm Kennedy 1 — Unbutton all of your sleeve buttons.

Forearm Kennedy 2 — Turn the cuff back over itself once.

Forearm Kennedy 3 — Pull the cuff up to your elbow so a few inches of your sleeve is inside out.

Forearm Kennedy 4 — Turn the inside out part over the cuff.

Forearm Kennedy 6 — It might take a little finagling :/

Forearm Kennedy 7 — Use your thumb to go all the way around the roll, especially to the thickest part at the back.

Make sure the sleeve is folded over the cuff cleanly.

Forearm Kennedy 10 — You should end up with a sliver of visible cuff (about 1/4 inch).

Forearm Kennedy sleeve roll — Clean and crisp!

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:

J Crew Roll 1 — Start with your sleeves unbuttoned.

J Crew Roll 2 — Pull your cuff up, just above the elbow.

J Crew Roll 3 — Placing your fingers inside the sleeve, turn it back and over the cuff.

J Crew Roll 4 — Work your way around the roll so it’s cleanly folded over the cuff.

J Crew Roll 5 — Leave 1/4 inch or so of cuff poking out the top of the roll.

J Crew Roll finishedJ Crew Roll side — The roll should be just above your elbow so you can bend your arms without restriction.

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.

J. Crew and a Half 1 — Start with the J. Crew Roll, then fold the entire roll in half.

J. Crew and a Half 2 — It’s a bit thick, so just try to keep it as clean as possible.

J. Crew and a Half 3 — Work your way around to the back of the roll to make sure there’s no twisting.

J. Crew and a Half sleeve roll front — Done! The roll is half as wide, and it sits slightly higher up on your arm.

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:

Three Turn 1 — Start with your sleeves unbuttoned.

Three Turn 2 — Fold the cuff back over itself once.

Three Turn 3 — Fold the cuff back over itself again…

Three Turn 4 — You guessed it – fold the roll back over itself one more time (for a total of three turns).

Three Turn 5 — The roll is four layers thick at this point, so it might take a little work to iron out any twists.

Three Turn 6 — Use your fingers to make sure everything is clean and tidy.

Three Turn 7 — Pull the roll down gently to finish.

Three Turn sleeve roll front — A sturdy sleeve roll that will stay in place all day long.

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.

Three and a Half 1 — Start with the Three Turn Roll in place.

Three and a Half 2 — Fold the roll in half, all the way around.

Three and a Half sleeve roll side — The result is a shorter, thicker roll that sits higher up on your arm.

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.

Four Turn 1 — Start with a crisp Three Turn Roll.

Four Turn 3 — The roll will be very thick, so take your time and avoid any twisting.

Four Turn 4 — Be sure to go all the way around the roll.

Four Turn sleeve roll front — Look at that clean, sturdy sleeve roll!

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).

Comments

Teddy says

December 1, 2020 at 11:28 am

Love the suggestions… I, however, have folded my cuffs inwardly … folding as i go… seem to make for a cleaner look and the shirt takes on a different appearance that is seamless without the clunkiness of the fold rising above the forearm… just a thought

Dean Italiano says

December 3, 2020 at 10:47 am

As a school Librarian, I’m balancing books on my forearms all the time and I don’t want them slipping off, so I quadruple roll ALL the time. Best trick? Do it BEOFRE you put the shirt on! While it’s on the hanger, quadruple roll and ensure the material is flat for each roll with both hands. Works like a charm, much easier.