Rules on Rolling: Shirt Sleeves

The J. Crew Look
The J. Crew Look

When rolling up your sleeves you
look like either a waiter or a presidential candidate. Politicians are always
taking off their jackets and rolling up their sleeves and pretending to help
build a house somewhere. It’s that getting-things-done look. I don’t buy it.
Part of my “keeping it real” policy means not rolling up my sleeves
unless there’s genuine work to be done

Rolling up your shirt sleeves can be
both a practical reaction and a social gesture, when done in the right

Roll Your Shirt Sleeves

You should be rolling up your
sleeves for one of three reasons:

  • Practical Necessity – If you’re doing work with your hands it’s
        appropriate to cuff your sleeves.  You can roll them back any time
        the shirt’s in danger of snagging or soiling because of the task at hand.
  • High Temperatures
        – A light cotton dress shirt is livable in most temperatures, but when it
        gets really bad rolling the sleeves up can give some needed relief. 
        Context matters here — you might be fine rolling your sleeves on the walk
        to work for most of the year, but rolling them up in the office should be
        reserved for real heat emergencies.  The key to this rule is to only
        exercise it when you really, really need to.
  • Deliberate Casualness – If you want to send a visual signal that you’re done
        with work or that you want everyone to relax a little you can roll the
        sleeves on up.  Do it when you want people to know that you’re ready
        to take things a little easier, and that it’s okay for them to do the same
        (this is especially useful for bosses trying to relax a tense atmosphere).

You’ll notice what you don’t see up
there “to look dramatic”.  Forget the Hollywood boardroom drama idea that
executives take their jackets off and roll their sleeves up when they’re
engineering big corporate takeovers or mass layoffs.  Rolling your sleeves
up in a meeting is just going to make you look sloppy.  Save it for when
you’re working with your hands or when you want to signal that stakes are
lowered and attitudes can relax a little, not for when you want everyone to
focus and care.


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