How to roll up your sleeves to look stylish?

The Secret Art of Rolling Up Your Dress Shirt Sleeves

May 23, 2020
By EllaH

Rolling up your dress shirt sleeves can be very dramatic. Watch any old Western film and notice how men take that extra moment to carefully fold their sleeves before landing a punch. Sleeves would also be rolled up in Hollywood movies when getting down to business and preparing to invest millions on the stock market.

In real life, however, rolling up your dress shirt sleeves is more a stylistic expression. We, women, don’t need the excuse of hot weather or of any other practical necessity to fold the sleeves. We do it because we like to. Rolled sleeves send a visual signal that says „relaxed“. They also look youthful and give off a statement of freedom.

Basic Sleeve-Rolling Guidelines

Before getting into the specific styles and methods of rolled sleeves, let’s just go over two general guidelines for rolling up your dress shirt sleeves.

Rule number one and perhaps the more important one: ensure that the rolled length on each arm is the same. Also, use the same roll on both arms to avoid looking lopsided.

Second, leave your rolled sleeves below the elbow. Above the elbow roll is tighter on the arm and the look loses its casualness.

Also, if you find yourself rolling your dress shirt sleeves either because they are too short or too long, find a tailor and have them adjusted.

3 Methods for Rolling Up Your Dress Shirt Sleeves

While there is no “right” or “wrong” way to roll up your sleeves, certain sleeve rolls can look cleaner and sharper than others. Each method has its unique benefits and charm, but we have selected three that work great and are suitable for different occasions.

Rolling Method #1: The Casual Roll

The casual roll is the easiest and most intuitive way for rolling up your dress shirt sleeves. It is perfect for when you’re on-the-go as it is easy and can be achieved in seconds.

Just (1) unbutton the cuff and (2) turn it back once so that the inside of the cuff is facing out. Next, (3) using the cuff as a guide, fold it over once more and you are good to go.

The only problem with this roll is that it comes undone quite easily.

Rolling Method #2: The Basic Roll

This is a simple and effective technique for rolling up your dress shirt sleeves.

The two first steps are the same as for the casual roll: (1) unbutton the cuff, turn it back once, (2) then fold it over once more. Run hands inside to ensure the roll is loose enough and the fabric is smooth. (3) Now fold over one more time (this is the third fold).

Rolling Method #3: The Master Roll

The master roll will set you apart from the everyone else wearing a dress shirt. It will make your shirt sleeves come to life.

(1) Undo the buttons on the cuff and let the sleeve fall freely and (2) roll up the sleeve to about two widths of the cuff. (3) Roll from the bottom end of the sleeve once more to cover the cuff, leaving only the top end of the cuff exposed.

The outcome is snug, neat and great in or out of the office. The sleeves are locked in place and won’t come undone as the day progresses.

This method for rolling up your dress shirt sleeves is particularly stylish when your shirt has a contrast lining or design pattern on the inside of the cuff. Feel free to let enough of the inner cuff show to clearly display the lining, making it clear that you are deliberately showing off the shirt’s accent. It’s all about being unique. After all, the key to being the most stylish woman in the room lies in the details.