How to Roll your Shirt Sleeves

There can be times when a long sleeve shirt just feels too restrictive. Maybe you’re caught in a sudden heatwave: your forearms feel like they’re suffocating, and you just want to feel a cool, gentle breeze through your arm hairs. Maybe you’re having a few after work drinks and you need to make things a bit more casual. This is all fine; my ‘Bad Style Alarm’ doesn’t go off every time I see a man with his sleeves rolled up. Not every time anyway. There are certain things you need to consider though to avoid looking like a supply teacher at the end of his tether.

The Basic Roll:

The most intuitive way to roll your shirt sleeves, the basic roll also gives you more of a chance to roll your shirt sleeves to the desired height. Here’s how:

Roll 1, Blog size

  1. Undo both buttons on the cuff
  2. Fold the cuff over on itself
  3. Repeat the fold until you reach your desired height


The Master Roll:

The ‘fancier’ rolling technique, using the master roll is a good chance for you to show that you know what you’re doing sartorially (and to look down your nose at people doing the basic roll). The end result can also look a bit cleaner than the basic roll if you get it right, here’s how:

Roll 2, Blog size

  1. Roll the sleeve up to two widths of the cuff
  2. Roll the sleeve on itself to cover the cuff
  3. Neaten and adjust the cuff to show as much or as little as you want


Of course, not all shirts are created equal. Avoid rolling up dress shirt sleeves, the cuff is generally too big and looks wrong when it’s rolled up. Something more casual like an Oxford Shirt looks great with a rolled up sleeve.

What about the rest of your wardrobe?

T-Shirts – A subtle fold on the sleeve can stop the unflattering ‘sleeve flare’ that make your T-shirts look like they don’t fit.

Knitwear – It might be tempting to give your jumper sleeves a little push up the arm, but try not to. This can stretch the wrists and make your sleeve hang lose.

Blazer – Whoa there, steady on Miami Vice.