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How to Roll up Dress Shirt Sleeves Like a Zen Master


When the going gets tough, the tough start by rolling up their sleeves. Rolling up your sleeves shows that you’re not panicking and running around like a headless chicken. It shows your intent, to get down to business, get your hands dirty and get shit done. Here’s a quick and easy guide to rolling up your sleeves like a cool customer.

Is there a Right or Wrong Way?  

You obviously watch Jim Cramer for his stock market expertise and not his sartorial splendor.

While there is no “right” or “wrong” way to roll up your sleeves, but certain sleeve rolls can look cleaner and sharper than others. As a general rule, you want to minimize the number of folds to avoid that bulky, bunched-up sleeve look that Popeye and the Michelin Man might favor. It helps to wear slimmer, form-fitting shirts as rolling the sleeves on a loose, billowy shirt will only exacerbate the look.

If your current technique is resulting in a roll that looks sloppy or won’t stay put throughout the day, we’ll teach you our best techniques for creating that sharp yet effortless sleeve roll.

“Politicians are always taking off their jackets and rolling up their sleeves and pretending to help build a house somewhere. It’s that getting-things-done look.”
– Glenn O’Brien, GQ Style Eye

Here are some techniques on how to roll up sleeves while you’re at work…

Basic Rule:

When rolling up cuffs, we suggest undoing both the cuff and gauntlet (the sleeve placket right above your cuff) buttons. Some people opt to leave the gauntlet button buttoned when rolling up their leaves to give it a snug, cleaner look but do so at the risk of stressing and tearing your sleeve placket or elbow. So to prevent any excessive wear on your shirt sleeves, we recommend always unbuttoning buttons on both the sleeve cuff and the gauntlet when rolling up cuffs.

The Classic Roll

A timeless and classy look, The Classic Roll is a mid-forearm, below-the-elbow roll that generally works for most men during the work day. We call it the Classic because well… it’s easy and you’ve probably done it numerous times. This roll is great to use in the office because you’re not exposing too much arm, making it appropriate for a more formal environment. So whether you’re actually cranking away or inconspicuously alt-tabbing between a spreadsheet and ESPN, The Classic Roll is at the very least, the simplest way to appear hard at work.

Step 1: Unbutton both the cuff and gauntlet button and fold over the cuff so that the inside of the cuff is facing out.

Step 2: Using the cuff as a guide, fold over the length of the cuff.

Step 3: Go back to whatever you were doing and do it better.

The Happy Hour Roll

The Happy Hour Roll is an above-the-elbow roll best for the times when you’re in a more active physical state. Why is it called The Happy Hour Roll? Because this roll works best as you prepare to pound some beers with co-workers or help your attractive neighbor move some furniture – both activities resulting in happiness in that particular hour. The number of rolls and higher placement of the sleeve makes this roll a bit less formal but more casually stylish – perfect for a more “I-work-hard-but-play-hard-too” look.

Step 1: Grab the nearest bottle of beer, unbutton both the cuff and gauntlet button and fold over the cuff.

Step 2: Fold over again using the cuff as a guide. Make sure the fabric is flat and there is no bunched up fabric inside this second roll.

Step 3: Fold over one more time (this is the third fold). By now, the sleeve should be at or above your elbow. Pull up and adjust the sleeve as desired. Tuck in the fold all the way around for a cleaner look. As you can see, this technique looks best with a beer in hand and with slimmer, well-fitting shirts.  The extra folds on a baggy shirt can create a lot of unattractive fabric bunching around your arm.

The Inside-Out Roll

No, this isn’t your go-to roll at your favorite sushi joint. This one accomplishes the snug fit of The Happy Hour Roll without that third fold.

Step 1: Unbutton both the cuff and gauntlet button and fold back the cuff. Continue pulling your sleeve up until your initial fold is double the length of the cuff.

Step 2: Grab the end of the inside-out sleeve fabric and pull it over the inside-out cuff. See why we call it the Inside-Out Roll?

Step 3: Voila. Snug, neat and appropriate in or out of the office. You have the option of leaving the sleeve below or pulling it above the elbow. Feel free to leave a little bit of the cuff sticking out under the rolled over fabric, especially if the inside of your cuff has a contrasting color or pattern – because sometimes others should be privileged to get a peak as well.

Nick Wooster, the internet’s most photographed man, loves to roll up sleeves and reveal his tattoo sleeves.

Adjusting for Body Type

Depending on your body type, some rolls might work better than others. Play around with different rolls and if you discover something new, come tell us about it.

A Note about French Cuffs

The French Cuff is inherently more formal than barrel cuffs on a dress shirt, so rolling them up to dress the shirt down may be counter to the intent. That said, you never know when you’ll need to get your hands dirty. So if you must roll up your French cuffed shirt, make sure keep those dapper cuff links in a safe place and go with The Classic Roll. 

While this guide was not meant to be all-inclusive on how to roll up sleeves, we hope you enjoyed it and found it useful. Feel free to share your personal favorite rolls in the comments if we’ve didn’t mention them. If you have any questions, email us at concierge@blacklapel.com and we’d be happy to chat!

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26 thoughts on “How to Roll up Dress Shirt Sleeves Like a Zen Master”

  1. Josh says:

    Hi guys,

    I like folding my cuffs in half to create a slimmer roll. I usually fold the cuff in half, and then continue folding it four more times, for a total of five folds including the initial halving of the cuff. Is this look acceptable? Please and thank you.

  2. James says:

    If wearing matching slacks and vest over a shirt and tie, is it appropriate to roll the sleeves?

    The pants/vest are a mid-charcoal grey. The shirt is a white/black gingham print. The tie is black.

    1. Black Lapel says:

      Yes! Appropriate sleeve rolling typically depends on the occasion or activity, not the outfit — however we don’t recommend throwing your suit jacket or blazer on top of a rolled shirt because that’ll just look weird. Otherwise, this outfit sounds most suitable for the classic and inside-out rolls we mention above.

  3. brian says:

    just bought an expensive shirt. it has a fancy design on the inside of the cuff. only problem is if i fold once showing the design it is a really loose sloppy half fold. if i fold a second time in the traditional fold the design will not be seen. alternatively i have tried to button the fancy cuffs once folded inside out in order to show the design but it becomes too tight and can’t bypass my wrist which ends up looking like a shirt which is too short.

    suggestions please?

    1. Black Lapel says:

      Brian, we recommend a modified Inside-Out Roll. For the final fold, don’t cover the initial roll all the way and let some of that fancy design show. Enjoy!

    2. Black Lapel says:

      Sounds like those fancy cuffs are going to be your little secret, Brian. That’s okay though. Actually, it’s more than okay, it’s good. Men need more secret style. Think about how badass they look when someone else is “helping” you get undressed. It’s the details like these that say “you’re making the right choices” to anyone who uncovers them.

      What’s that? You say you paid good money for this particular detail and want to show it off to more than just your honey? In that case try folding the cuffs over once and then using our Tie Clip Style Hack that we highlighted in our Hacks-essorize story from last summer.

  4. Farooq says:

    Loved the inside out roll……

    1. Black Lapel says:

      It’s almost sleeve rolling season, and we’ll be loving it with you soon!

  5. Collin says:

    I have a solid red shirt with a plaid pattern on the inside of the cuff- what’s the best way to roll it up to elbow length while showcasing the pattern- is there a name for that type of sleeve roll!

    1. Black Lapel says:

      There are several options, Collin. You can do just the first step of the Classic Roll and then simply push your cuff up to the elbow. We must warn you, though, if your forearms are closer to Olive Oyl’s than they are to Popeye’s you may not want to try this move or you’ll be constantly pushing your sleeves back up to your elbow. If that’s the case, stick with what we said in Step 3 of the Inside-Out Roll and let the inside of your shirt cuff peek out to show off some of the plaid.


    i tend to roll the sleeve 3 times so it finishes up mid forearm. I have been rolling my sleeves up since i was at school and i just enjoy the comfort it offers. I could not imagine having them buttoned down at the wrist. Ugh!!!

    1. Black Lapel says:

      This is a good look, David. Sounds like you do it year-round. It’s been a tough winter here at Black Lapel HQ, New York, so our forearms haven’t made many appearances, but soon we’ll be rolling our sleeves with you!

  7. +Roger Burgess says:

    If for whatever reason you have to wear baggy shirts, making one further roll more than the happy hour roll gives the shirt a look that compliments the baggy-ness in a way that manages to rescue whatever style is possible with the shirt. It gives the rolled cuffs a thick meaty look and they sit right at (for thinner arms) or just above your biceps (for more athletic ones).

    It does take practice though, four rolls is hard to pull off smoothly with one hand.

    Apologies for the thread necro. Figured I’d share a tip familiar to every jarhead in existence but not well known outside that fraternity.

    1. Black Lapel says:

      No need to apologize, Roger, helpful comments like this are welcome anytime. Thanks for the great tip/add-on!

  8. Bianca says:

    I don’t have a hard time rolling up my sleeves because they’re… well, mine. But I was looking for some different ways to roll them up for my brother. This is pretty cool.

    1. Black Lapel says:

      Way to show some brotherly love! Glad to be of service.

  9. Brian says:

    I have to admit, I prefer rolling my sleeves up both at work and outside of work. The Classic is obviously more work appropriate and the Happy Hour for apres work or weekends. Either way, anything is preferable to wearing a short sleeved “formal” shirt to work!

    1. Black Lapel says:

      Here here, Brian. Leave the short sleeve dress shirts to Dwight Shrute.

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    1. Black Lapel says:

      Thanks for the kudos! Let us know if there’s anything specific you’d like us to address in the future!

  11. Jessy says:

    I always use the inside-out roll, it’s the one that seems to work the best with the baggy work shirt I have to wear.

    1. Black Lapel says:

      Now that you’ve got a Black Lapel shirt, give the Classic a try! It won’t flail about nearly as much with a slim fitting sleeve.

  12. 3ric McNéw says:

    I favor the British version (look up a pict of christopher hitchens), basically a classic roll but done INSIDE the sleeve rather than outside. stays up better for me

  13. Rodrigo says:

    As somebody who is occasionally required to roll his sleeves up at work, I’ve mastered the classic. I don’t like the triple fold of the “happy hour” for myself, but have yet to try the “inside out”. On the to-do list… simple minds, simple pleasures?

    1. Black Lapel says:

      Awesome, let us know how you like it!

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