How To Roll Up Your Sleeves

Rolled up sleeves is a good look. It’s like a grown-up’s t-shirt, but you shouldn’t roll your sleeves up every time you put on a shirt. There are times when it’s appropriate and times when it isn’t.

For me, there are a three reasons you might want to roll up your sleeves.

  • The first is a physical necessity. Maybe that necessity is the heat. Wearing dress shirts in the summer can get hot. Or, it might be that you’d get your sleeves dirty. Either way, you are doing it for a physical reason.
  • The second is to send a casual/relaxed signal to everyone else. Your work environment might already be casual, and everyone rolls their sleeves. Maybe it’s Friday; it’s the end of the day, and everyone is going out for drinks. Go ahead. Roll ’em up!
  • Third, it’s a way to dress down a shirt. This is a simple solution to a problem everyone dreads. How formal is this occasion/party/restaurant going to be? A dress shirt can take on many different forms. Formal? Shirt and tie. Casual? Lose the tie and roll up your sleeves.

The next question is, how high do I roll my sleeves? Mid-forearm or above the elbow? The forearm should be your go to. It’s casual and looks good. If you are actually doing something physical, however, you may prefer to go above the elbow for more range of motion.

Now let’s talk about how to roll those sleeves up. There are two main ways.

The first is the classic roll. The classic roll is good for rolling to the forearm.

Classic Roll

To do this, you roll the cuff back using the cuff width as a guide. The down side to this is the shirt becomes more constrictive the higher you go. If you are rolling above the elbow, this second way may be more useful.

The “Inside-Out Roll” or the “Master Roll” is good for forearm or for above the elbow.

rolling up sleeves

Step 1: Fold sleeve inside out, putting the cuff where you want it to finish (2 or 3 cuff widths high)

rolling up sleeves

Step 2: Roll your sleeve starting at the bottom using about a cuff width each time

rolling up sleeves

Step 3: Make it nice and neat

Many people find this roll is less restrictive. Experiment and see which you like best.

Now get out there, and get your roll on.


“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 (The Style Guy)



4 thoughts on “How To Roll Up Your Sleeves

  1. Pingback: Using the Master Roll With Contrasting Cuffs | Up Your Fashion Game

  2. I didn’t even know there are different ways to roll up your sleeves! I just went through your entire blog and found it super userfull. Keep up the great work!

  3. Pingback: How To Roll Shirt Sleeves? The Italian Style! -

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