How & When to Roll Up Your Shirt Sleeves – Dress Shirts and Sleeve Rolling Guide

Rolling up your shirt sleeves is both a practical reaction and a social gesture.

Whether you’re wearing a dress shirt, long-sleeved work shirt, or sweater the way in which you do this “simple” task range from simple and intuitive to planned and thought out.

In either case – you always want a rolled sleeve look to look effortless.

Even if it takes you a bit of effort to achieve the look.

The Italians call this Sprezzatura – the art of concealing the pains it took to perfect something.

I call this giving a damn about your personal appearance and taking the time to master a look through practice and knowledge.

Either way – pay attention to the small things. Like a pinch of salt – they can do wonders for adding flavor to an outfit.

FYI – in this article we won’t be talking about rolling up suit coats or sports jacket sleeves. This isn’t normally practical, as in most instances it’s easier to simply take the jacket off.

Why 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.

Here a video summary on why to roll your shirt sleeves and why not to mix rolling your shirt sleeves with a tie.

How to Roll Your Sleeves Up

So you’re in a situation where it’s all right to roll the sleeves up. What’s the gentlemanly way to do it? There are dozens of ways – here we highlight four. [more...]

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