How to Roll Up Shirt Sleeves for Style & Comfort

“Rolling up your sleeves” is more than just a metaphor for getting ready to work. The physical act of rolling up your sleeves can do a lot. It can “cool off” an outfit for outdoor use. It can make a business outfit look more “business casual.” And it can completely change your silhouette. However, many of us love the look of rolled-up sleeves, but we don’t know how to do it in a way that both looks good and stays put. That’s why we’re here to show you how to roll up shirt sleeves for style and comfort in three different ways.

The Casual Roll

This is a great roll if you’re doing a task that requires a temporary roll in your sleeves. In other words, it’s great for getting your arms free temporarily—but won’t necessarily stick that way all day long. Here are a few tips for pulling off the casual roll:

  • Unbutton the cuff (Both buttons)
  • Roll the cuff by its seam. This is the “first roll”
  • Sticking to the same width as the first roll, double that roll
  • Tuck the exposed corners of your cuffs in to make the overall look neater

The casual roll will rest below the elbow if you do it right, opening your sleeve up for additional air. This type of roll is also referred to as the “AIFA” roll.

The Basic Roll

Although you might expect rolls with names as similar as “casual” and “basic” to be the same, there’s actually a subtle difference here:

  • Roll according to the same rules of the “Casual Roll”
  • Roll your cuff a third time rather than stopping after two folds
  • As before, cinch the roll off

This will finish your roll a little higher on your arm, giving you more reliability for keeping it from slipping down. But keep in mind that in some casual situations—like going out with friends—this may look a little too utilitarian and less fashion-forward.

In addition, you can also add another roll to get your roll higher on the arm, which is better for performing labor.

The Master Roll

With the Master Roll, you’ll have a convenient way to keep your shirt rolled on your arm all day. You’ll also find it convenient to undo this roll at the end of the day with just one movement. Here’s how to do it:

  • Fold the cuff further up the sleeve so there’s additional fabric before your first fold.
  • Using that folded fabric, fold the next piece of fabric over it. Cinch it in place

This type of roll will give you the most fashion-forward look!

Which Should You Choose?

So, which roll should you choose? For instance, let’s say that you want a quick roll for a good look with your outfit. Should the roll end above or below the elbow? For fashion’s sake, a casual roll below the elbow will look far better, as it doesn’t have to be practical—it just has to look good and stick. If you’re rolling up your sleeves to do some real work, then try to get the sleeves above the elbow.

Shop Tops from Vintage 1946

Now you know how to roll up shirt sleeves for style and comfort. You just need some great sleeves to practice on! We recommend shopping the shirts at Vintage 1946 so you can try these rolls for yourself.