How to Roll Up Your Sleeves the Right Way 5 foolproof, fashionable ways to keep your sleeves up

Historically, the act of rolling up one’s sleeves has been a symbol of “getting down to business.” Whether a man is gearing up for physical labor, getting ready to throw a right jab, or relaxing with a nice cold brew after a hard day’s work, rolling up your sleeves is always a sign that you’re a man’s man.

The popularity of rolled sleeves finds its origins in the uniforms of military men. During the spring and summer months, Marines famously don desert camouflage utilities in non-combat areas and roll their sleeves up as a way to keep cool. This look has been adopted into the everyday wardrobe practices of men and women. Today, the act of rolling one’s sleeves is no longer strictly an act of utility, but more of a deliberate style statement. Men and women alike roll their sleeves for a variety of reasons. Some roll to protect expensive clothing from damage when undertaking some dirty work. Some revel in the increased freedom of movement. Some find that rolled sleeves help to beat the heat. Others simply like the look.

While you may be thinking that rolling your sleeves is a no-brainer and that there is little need to go into detail about such matters, you might be surprised to learn that there are actually several techniques for sleeve rolling. Each method has it unique benefits and charm. Here, we break down our 5 favorite sleeve rolling techniques. Whether you’re baring your arms for utility’s sake or to serve your personal style, be sure to try out each technique to see which method suits you best.

The Classic

The Classic

The most traditional and intuitive of sleeve rolling methods, the Classic involves evenly folding sleeve cuffs repeatedly until you are satisfied with your sleeve length. This technique is great for thicker shirts like flannel and chambray.

  1. Begin with your sleeve fully extended to your wrist with the buttons unbuttoned.
  2. Fold the cuff upward once until it is inside-out.
  3. Continue rolling the cuff upward until the desired length is achieved. This method looks great when rolled up just below your elbows, revealing only about a third of your arms.

The Marine

The Marine

Similar to but more precise than the Classic, the Marine starts out with–preferably ironed–sleeves laid flat on a table and rolled up before the shirt is put on. This method results in the most crisp and uniform sleeves, but is also the most time-consuming way of sleeve rolling.

  1. Lay your sleeve flat out on a table (preferably immediately after ironing).
  2. Fold the cuff upward once until it is inside-out.
  3. Straighten the fold out and flatten. Your first fold should be very neat, crisp, and wrinkle-free.
  4. Fold the cuff up again, repeating steps 2 and 3 until you reach your preferred height. This technique lends itself nicely to sitting higher up on the arm, typically at or above the elbow.

The J. Crew

The J. Crew

This is the way that J. Crew styles their models’ and mannequins’ sleeves, and it’s an easy way to add a bit of sprezzatura or planned messiness to your ensemble. This roll is perfect for shirts that have a contrasting color or design on the cuff/interior, and is also the least constricting method of rolling one’s sleeves.

  1. Start with your sleeves fully extended and unbuttoned.
  2. Roll your sleeve up about two widths of the cuff.
  3. Roll up again to the bottom of the cuff.
  4. Roll one final time, leaving the top of the cuff slightly exposed.

The One N’ Done

The One-N-Done

Perfect for when you want to pair a collared shirt with a pullover sweater, this method lets both shirts shine.

  1. With both the collared shirt and sweater on, pull the sleeves of your collared shirt down so that they are showing underneath your sweater.
  2. Flip your cuffs and fold them over once so that they are folded above the ends of your sweater sleeves.
  3. Either re-button your cuffs or leave them be.

The Cardigan Roll

The Cardigan Roll

This roll is meant for applying when wearing a button-down shirt and a cardigan. Rather than rolling both your shirt and jacket sleeves together–which would result in a restricting and frankly uncomfortable roll–do each separately to create a cohesive look that doesn’t disrupt your mobility.

  1. Start by pushing the sleeves of your cardigan/lightweight jacket up to your elbows.
  2. Do a J. Crew roll with your shirt sleeves.
  3. Tuck your cardigan sleeves into your J. Crew roll and adjust accordingly to make the layers look cohesive.