How & When to Roll Up Your Shirt Sleeves – Dress Shirts and Sleeve Rolling Guide

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.

Rolling Men's Shirt Sleeves

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 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.

A Man's Guide To Style

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.Unbutton Shirt Sleeves - Men Style Tips
  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.Fold the dress shirt cuff inside - Men Style Tips
  3. Fold the bottom of the inside-out sleeve about halfway up so that it makes a band beneath the inside-out cuff.
  4. Adjust until you’re happy, leaving the unbuttoned and inside-out ends of the cuff sticking out of the rolled fabric.

Adjust the dress shirt sleeves - Men Style Tips

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.
  2. Using the cuff as the measuring point, we simply roll the sleeve over itself 1-2 times, stopping below the elbow.Roll the sleeves 1-2 times - Men Style Tips
  3. Adjust until you’re happy.Men's Rolled up Sleeves

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.
  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.Change of Command - Folded Sleeves

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 non-defined 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!