How to Roll Up Your Sleeves the Right Way

5 foolproof, fashionable ways
to keep your sleeves up

Written by RJ Firchau

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
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
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

  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.
RJ Firchau

Kayode Ojo
Kayode Emmanuel Ojo is the Co-Founder and Managing Director at SHEFFA Limited. He is presently studying Computer Science at the National Open University, Victoria Island, Lagos.