1. How and When to Roll Up Your Shirt Sleeves –
Dress Shirts and Sleeve Rolling Guide
by Antonio
Rolling up your shirt sleeves is both a practical reaction and a social
gesture.
Whether you’re wearing a dress shirt, long-sleeved work shirt, or sweater the way in which you do this
“simple” task range from simple and intuitive to planned and thought out.
In either case – you always want a rolled sleeve look to look effortless.
Even if it takes you a bit of effort to achieve the look.
The Italians call this Sprezzatura – the art of concealing the pains it took to perfect something.
I call this giving a damn about your personal appearance and taking the time to master a look through
practice and knowledge.
Either way – pay attention to the small things. Like a pinch of salt – they can do wonders for adding flavor
to an outfit.
FYI – in this article we won’t be talking about rolling up suit coats or sports jacket sleeves. This isn’t
normally practical, as in most instances it’s easier to simply take the jacket off.
Why Roll Your Shirt Sleeves
You should be rolling up your sleeves for one of three reasons:
•
Practical Necessity – If you’re doing work with your hands it’s appropriate to cuff your sleeves.
You can roll them back any time the shirt’s in danger of snagging or soiling because of the task at
hand.
•
High Temperatures – A light cotton dress shirt is livable in most temperatures, but when it gets
really bad rolling the sleeves up can give some needed relief. Context matters here — you might be
fine rolling your sleeves on the walk to work for most of the year, but rolling them up in the office
should be reserved for real heat emergencies. The key to this rule is to only exercise it when you
really, really need to.
•
Deliberate Casualness – If you want to send a visual signal that you’re done with work or that you
want everyone to relax a little you can roll the sleeves on up. Do it when you want people to know

2. that you’re ready to take things a little easier, and that it’s okay for them to do the same (this is
especially useful for bosses trying to relax a tense atmosphere).
You’ll notice what you don’t see up there “to look dramatic”. Forget the Hollywood boardroom drama idea
that executives take their jackets off and roll their sleeves up when they’re engineering big corporate
takeovers or mass layoffs. Rolling your sleeves up in a meeting is just going to make you look sloppy. Save
it for when you’re working with your hands or when you want to signal that stakes are lowered and attitudes
can relax a little, not for when you want everyone to focus and care.
Here is my video summary on why to roll your shirt sleeves and why not to mix rolling your shirt
sleeves with a tie.
How to Roll Your Sleeves Up
So you’re in a situation where it’s all right to roll the sleeves up. What’s the gentlemanly way to do it?
There are dozens of ways – here we highlight four.
Method One: The Basic Sleeve Fold
Perhaps the most intuitive fold, this is what most of us would naturally do when we roll our shirt sleeves for
the first time. This is the hardest fold to undo and aesthetically the worst looking. However it’s simplicity
and ruggedness make it a staple for the working man.
1. Unbutton the cuff and any gauntlet buttons further up the sleeve.
2. Using the cuff as the measuring point, we simply roll the sleeve over itself until it passes the elbow.
For me this is 3 times – depending on your cuff size and arm length, it may be 4 or as few as 2.
3. Adjust until you’re happy, although its better to ensure each fold is clean and straight to get the best
final look.
Method Two: The Master Sleeve Roll
Depending on how well you finish the final fold, you can have either a more casual look with the end of the
cuff is still showing, turned inside out and shoved up your sleeve. This gives a decidedly more rumpled look
that many consider stylish – especially if the shirt has a contrasting cuff color that pops.
1. Again, unbutton the cuff and any “gauntlet” buttons further up the sleeve.

3. 2. Fold the cuff inside-out and keep tugging, without folding, until you’ve exposed just a little less arm
than you want to with your finished look. The turned-back sleeve should just be inside out and
unfolded at this point.
3. Fold the bottom of the inside-out sleeve about halfway up so that it makes a band beneath the insideout cuff.
4. Adjust until you’re happy, leaving the unbuttoned and inside-out ends of the cuff sticking out of the
rolled fabric.
Method Three: The AIFA Roll
This is a casual roll for the man wanting to signal the work day is over and it’s time to grab a beer. I sport
this sleeve roll when I’m walking around town and it’s a bit warmer – it looks stylish and I can easily roll the
sleeves down with no wrinkles. It is limited though by the size of your shirt cuff – too big of a cuff and this
roll is impractical.
1. Again, unbutton the cuff and any “gauntlet” buttons further up the sleeve.

4. 2. Using the cuff as the measuring point, we simply roll the sleeve over itself 1-2 times, stopping below
the elbow.
3. Adjust until you’re happy.
Method Four: The Devil Dog Fold (Not Shown in Video)
A crisp and professional look. We recommend this one for office settings and Marine Corps Change of
Commands. The finished effect is a band of cuffed cloth that’s even in width all around, with no corners or
buttonholes showing.
1. Unbutton the cuff and any gauntlet buttons higher up the sleeve.
2. Fold the cuff in half upwards, so that the very outer edge is folded back to meet the bottom edge of
the cuff.
3. Fold again, keeping the same width — half the width of the cuff — and tucking the end of the cuff
underneath the new fold.

5. 4. Keep going until you reach the desired height on your arm. The roll of folded fabric should be even
in width and should hide the cuff itself entirely.
What About Rolling Up Your Sleeves When You Have Thin Arms
Rolling up your shirt sleeves will draw attention to your biceps & triceps; for those that work out it’s a great
chance to show the world you take care of your body. For those of us with thinner builds or thick nondefined arms – this may be a bit embarrassing. In this situation you need to think proportion and strive
for balance.
•
•
•
Wear shirts that fit you and compliment your physique. Example – petite men should choose shirts
with smaller cuffs and thinner sleeves.
Keep your sleeve roll below your elbow – this looks better and draws the focus to your forearms vs.
your 10 inch biceps. Forearms are normally closer to an average size than biceps – which vary
greatly.
When rolling the shirt – roll the sleeve over on itself length-wise to reduce the sleeve width and
create a tighter fit on the bicep. A loose rolled sleeve only exaggerates already thin arms.
How Far Up to Roll Your Sleeves
You’ll notice there’s no measurements in inches or centimeters on either of our methods. That’s because
how far to roll the sleeves is up to you — with some caveats.
•
Above the elbow is a more practical place to keep the sleeves if you’re actually working with your
hands. Aesthetically though, it violates the “rule of thirds” and never looks quite as stylish as leaving
the rolled sleeve a bit below the elbow. Also, if you have a loose cuff or a lot of sleeve fabric it can
start to look odd as more and more fabric gets bunched up around your elbow ruining the line of your
bicep. Stick to thin, tightly-fitted shirts if you’re rolling your sleeves high.
•
Below the elbow is a less practical, more stylish option. It’s good in situations where you’re
deliberately trying to look relaxed, and works great with the . You may need to roll the turned-back
fabric over on itself a few more times to keep it tight on your forearms (unless you have very thick
arms), which will thin the finished band of cloth out some.
Lastly – here is a video overview of How to Roll your Shirt Sleeves
Remember – pick the rolled sleeve look that works for you and rock it with confidence. As long as you keep
it clean and simple with an effortless look – you’ll look great!

6. 4. Keep going until you reach the desired height on your arm. The roll of folded fabric should be even
in width and should hide the cuff itself entirely.
What About Rolling Up Your Sleeves When You Have Thin Arms
Rolling up your shirt sleeves will draw attention to your biceps & triceps; for those that work out it’s a great
chance to show the world you take care of your body. For those of us with thinner builds or thick nondefined arms – this may be a bit embarrassing. In this situation you need to think proportion and strive
for balance.
•
•
•
Wear shirts that fit you and compliment your physique. Example – petite men should choose shirts
with smaller cuffs and thinner sleeves.
Keep your sleeve roll below your elbow – this looks better and draws the focus to your forearms vs.
your 10 inch biceps. Forearms are normally closer to an average size than biceps – which vary
greatly.
When rolling the shirt – roll the sleeve over on itself length-wise to reduce the sleeve width and
create a tighter fit on the bicep. A loose rolled sleeve only exaggerates already thin arms.
How Far Up to Roll Your Sleeves
You’ll notice there’s no measurements in inches or centimeters on either of our methods. That’s because
how far to roll the sleeves is up to you — with some caveats.
•
Above the elbow is a more practical place to keep the sleeves if you’re actually working with your
hands. Aesthetically though, it violates the “rule of thirds” and never looks quite as stylish as leaving
the rolled sleeve a bit below the elbow. Also, if you have a loose cuff or a lot of sleeve fabric it can
start to look odd as more and more fabric gets bunched up around your elbow ruining the line of your
bicep. Stick to thin, tightly-fitted shirts if you’re rolling your sleeves high.
•
Below the elbow is a less practical, more stylish option. It’s good in situations where you’re
deliberately trying to look relaxed, and works great with the . You may need to roll the turned-back
fabric over on itself a few more times to keep it tight on your forearms (unless you have very thick
arms), which will thin the finished band of cloth out some.
Lastly – here is a video overview of How to Roll your Shirt Sleeves
Remember – pick the rolled sleeve look that works for you and rock it with confidence. As long as you keep
it clean and simple with an effortless look – you’ll look great!