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!

  • Patrick

    Doesn’t the devil dog destroy the cuffs?

  • Antonio Centeno

    Patrick – technically a Devil Dog can destroy anything!    

    But no, I haven’t seen this fold damage cuffs:)

  • Eric

    Is there any way to fold french cuffs without them looking ridiculous?  I’ve tried a few times and failed a few times.

  • Wordgrouper

    Who knew? Four ways to roll a sleeve? I’ve always enjoyed my sleeves rolled (usually the basic or AIFA, as I now know) because I thought the look was casual, laid-back, and relaxed. Now that I think about, however, I realize I got into the habit of rolling my sleeves because my shirts never fit well, the sleeves being usually too short. 

  • Steven E

    Wow! Great article. I love rolling up my sleeves at work. My work doesn’t really have a dress code so rolling up my sleeves gives me a more casual look. I use the master sleeve fold as I think it looks best. Also, I roll my sleeves up at school mostly because of the hot weather.

  • Wim Boerée

    I always use the simple fold, but after reading this and watching your video’s i decide i’m going to use the master sleeve roll, it seems way more practical and less time consuming. Most of the time I roll up my sleeves at school and the master roll seems way easier and less time consuming, and ofcourse, gives more space for your arms. Thank you for this guide.

  • Brian

    I thought there were only two ways to roll your sleeves, above or below the elbow. I am going to have to try the master fold and the devil dog. The section on skinny arms was cluth too, although I usually keep my shirt rolled below my elbow.

  • David Grega

    Love this post. I’ve always been very conscious of how and when I roll my selves. Not all rolls work for my body type, I have short muscular arms. I’ve fond two clean even folds while only unbuttoning the cuff button keeps things symmetrical and tight while still giving a relaxed impression and if need be you can return your sleeve to a full buttoned position without a terrible amount of wrinkling. I also find this type of roll and others to be a great way to expose a nice watch that compliments your overall look. Cheers!

  • Nwsutton

    Great article.  Thanks Anthony.  When I used to work in an office everyday, I’d find myself rolling my sleeves up more time than not.  Sometimes it was because I had a shirt that I really liked, that had unfortunately shrunk a bit over time, so a roll or two of the sleeves hid the fact that it was too short in the sleeve.  Other times, it was due to overheating.  However, with this new information, I will definitely be more conscious of this tactic in the future.

  • Andy Rathcoe

    Thanks for a very detailed and useful post on the art and science of sleeve rolling. I have worked in the media industry for many years and seen several fashion and style trends come and go through the workplace but one always endures: apparently casually rolled up sleeves. Some get it right and some get it wrong (those who get it wrong should read your post in order to correct their erroneous ways!) but it is absolutely ‘de rigeur’ in my industry sector. Only one problem still baffles many, however experienced they are in selecting and implementing the best sleeve roll for them in any given situation: how to manage unrolling them to replace a jacket?

  • geoffrey.cubbage

    @Andy Rathcoe Thanks for the comment — rolling the sleeves back down before putting a jacket on is a definite must. They’ll probably need to either be worn under the jacket or rolled up from then on, as well, until they can be ironed or at least laundered to take the wrinkles out.

  • geoffrey.cubbage

    We didn’t put it in the article, but that’s a very good point — rolling the sleeves can be a way to keep a well-loved but regrettably-shrunken shirt in the wardrobe, provided you’re only wearing it on warm days and in casual settings!

  • geoffrey.cubbage

    A great way to show a nice watch off without being ostentatious about it, for sure. Muscular men definitely need a little less rolling — I’ve got long, thin arms myself, so a “Master Sleeve Roll” (#2 up there) with two or three good thick foldings-over is the only way to keep the cuff from sliding back down unbuttoned.

  • geoffrey.cubbage

    I’m a skinny-armed man myself — it took me a while to settle on the right balance between looking streamlined and not having my unbuttoned cuffs flopping back down mid-gesture. Glad the article was helpful!

  • geoffrey.cubbage

    Glad we could help! Enjoy your new style.

  • geoffrey.cubbage

    The relaxed dress codes are definitely getting more and more common — glad this one could be of use to so many men!

  • geoffrey.cubbage

    It’s definitely a way to save a slightly-too-short shirt, but only works for shirts you save for casual settings and warm weather — nothing looks worse than a too-short shirt with wrinkles all up and down the forearm from previous sleeve-rolling. Have a few that are long enough in the arm for cooler weather and wearing with jackets and suits, at least!

  • geoffrey.cubbage

    Good question! We need to do a full article on French cuffs, to be honest, but briefly I’d say that you can double the cuff back and then use #1 (the basic roll) to hide the extra fabric. You’ll run into trouble with contrasting French cuffs though (white-on-color or color-on-different-color) — better not to try rolling those. In general it’s an odd clash between a more formal cuff style and a less formal way of wearing it, so I’d say try to avoid doing it, and try to disguise the fact that it’s a French-cuffed shirt if you do.

  • jonathanpike

    Thanks for all of this information, Antonio. I, like many other commenters, had never heard about anything but the basic roll. I have a couple of shirts with colourful cuffs that the master roll would look really good with, and I’m really excited to try it out!

  • geoffrey.cubbage

    @jonathanpike Contrast cuffs (with color inside the cuff that’s different from the outside) are definitely some of the best ones for rolling! And if you’re handy with a needle and thread, or you have a friend who is, they’re easy to add to just about any casual shirt, too…

  • brianst62

    With regard to French cuff, I tend to roll the cuff twice (the AIFA roll?) , leaving the cufflinks in the cuff. It seems to work OK and looks good too. I agree that this is a more “after work” look. Over the elbow would be a casual weekend look as far as I am concerned. It is especially comfortable if the shirt is more roomy. I have never been a fan of short sleeved formal shirts, thus have always rolled long sleeves up.

  • danielrmich

    I just came across this really interesting alternative to rolling up sleeves.  Its an elastic cufflink of sorts that lets you just slide your sleeves up and then they stay put.