Traditionally, there’s nothing that means business more than rolling up your shirt sleeves. It’s a man’s way of saying, I’m about to get my “hands dirty” and do some work. But for the stylish gentleman, it’s also one of the classic ways to dress down a shirt with effortless flair, especially in the summer heat.

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.

Nick Wooster, the most photographed man on the internet, is known to favor a high Happy Hour Roll to expose a permanent sleeve of artwork beneath his shirt sleeve.  

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.

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 and we’d be happy to chat!

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