Shirt sleeves should be rolled up in an effortless manner that conveys ease, in spite of the forethought and effort that has been required for it. This has been perfected by the Italian art of Sprezzatura- the art of concealing the pains it takes to perfect an art.

Why Should Shirt Sleeves Be Rolled Up

  1. Practicality: When doing menial work with one’s hands, it is better to fold back the cuffs of one’s sleeves. This prevents unnecessary snagging or dirtying of the shirt.
  2. Temperature: Cotton shirts are normally considered light enough to wear in most temperatures. It makes sense to roll up sleeves when one is out for a walk, but in the office this gesture indicates extreme urgency.
  3. Casualness: If one wants to purposefully convey that he is done with work and is relaxing, the shirt sleeves can be rolled up deliberately. This also enables bosses to send their employees a signal that the latter can also do so after a tense work shift.

Rolling up one’s sleeves looks careless during a meeting, and not at all poignant in the way actors do so on the big screen.

Rolling up your dress shirt sleeves

How to Roll Your Sleeves Up

The Basic Sleeve Fold
This is the hardest fold to undo and looks scruffy. However, its simplicity makes this easy for working men.

  1. Unbutton the cuff and gauntlet buttons further up the sleeve.
  2. Starting from the cuff, roll the sleeve until it crosses the elbow.
  3. Adjust to ascertain that the folds are straight.

The AIFA Roll
This casual gesture indicates the end of a day of work and time to go for relaxation. However, it is limited by the cuff-size.

  1. Unbutton the cuff and gauntlet buttons further up the sleeve.
  2. Starting from the cuff, roll the sleeve roughly twice and stop below the elbow.
  3. Adjust.

The Master Sleeve Fold
Depending on the last fold, this look can be combined with a rumpled texture and contrasting color cuff in order to become stylish.

  1. Unbutton the cuff and gauntlet buttons further up the sleeve.
  2. Fold the cuff inside-out, and keep pulling without folding. Finish just a little beyond where the arm is intended to be exposed. The sleeve should be inside out and unfolded.
  3. Fold the bottom of this sleeve half-way to make a band beneath the same cuff.
  4. Adjust, and leave the unbuttoned ends of the cuff sticking out.

The Devil Dog Fold
Extremely professional, this fold produced an even width of cuffed cloth with no edges or buttonholes showing.

  1. Unbutton the cuff and gauntlet buttons further up the sleeve.
  2. Fold the cuff in half, so that the outer edge touches the bottom edge of the cuff.
  3. Fold again with the same width and tuck the end of the cuff beneath the new fold.
  4. Continue until you reach the requisite length.

Should I roll my dress shirt sleeves?

Rolling Up Sleeves When One Has Thin Arms
The aim should be for proportion and balance. Shirts should fit properly, and on thinner men should have smaller cuffs and thinner sleeves. Sleeves should preferably be rolled below the elbow and should be tightly rolled when drawn up.

How Far To Roll Up Sleeves

  1. Above the elbow when working with hands.
  2. Below the elbow for a more stylish look.