How & When to Roll Up Sleeves: 3 Sleeve Styles

Request from a Cladwell enthusiast on how to roll your sleeves:

The other night my wife and I wanted to get drinks after work at a semi-fancy place near our house, so I exchanged the T-shirt I was wearing for a flannel button-up shirt that I bought because a small part of me likes to pretend I'm just like Tim Riggins on Friday Night Lights. Though it was past 6, it was still hot outside, so I thought to myself, "No problem. I know just what to do." Well, I fumbled with the sleeves for a while, and eventually managed something that I thought was passable. But before we left I looked in the mirror and what I saw was disappointing, and more than in just the usual ways (thinning hair, skinny legs, shoes my father would think were cool, etc.). One cuff was sticking out sideways, and the other looked like it had been trampled by that entire stampede of wallabies from The Lion King. And the worst part of all this is that when I bought the shirt the sleeves came rolled and looked absolutely perfect, so I couldn't resort to my typical line of excuses which hold that I'm the last person at fault when anything, anywhere goes wrong. So, Cladwell, what gives? What's wrong with me? Why can't I roll up my sleeves in a manner that looks halfway passable? What am I doing wrong? Any advice on how to roll up sleeves would be most excellent! 

Before we get into the technique of rolling your sleeves, here are a few guidelines to follow:

When should you roll your sleeves? - When you’re doing hands on work. - When the temperature is sweltering. - When you’re in a casual situation.

Why should you roll your sleeves? - It’s hot out! - Casual situations call for loosening up and throwing a little bit of swag in your outfit (sleeve swag that is). Rolling shows more of your arm, which is considered more casual. - You don’t want your sleeves getting caught up in whatever kind of work you’re doing; ie. painting, lifting, cutting, sawing, whatever it is.


1. The Basic Roll - the go-to roll for most, simply because it’s the first that comes to mind. - Simply fold your un-buttoned cuff back 2-3 times, using the length of the cuff to determine the length of the roll. - Make sure the roll is the same length all the way around and flat.

2. The Business Roll – this is perfect for businessmen ready to relax after a hard day at the office. It allows for airflow to the part of the arm covered and keeps you looking professional, you get the best of both worlds! - Fold the unbuttoned cuff backwards 1-2 times over itself; make sure it does not go past your elbow. - Tada! You have your roll. Adjust until you’re satisfied. - Don’t forget to make sure the roll is the same length all the way around and flat.

3. The Perfect Roll – or what I like to call the “swag roll," this is the most comfortable and perhaps most casual roll, leaving a little more room for movement. It’s also a great roll for adding a little sleeve swag into your outfit. - Fold the un-buttoned cuff backwards, pulling it continuously up your arm until it is slightly longer than where you want the roll to end on your arm (should be inside out). - Take the part of the sleeve under the cuff and fold it up, towards the cuff. - Make sure the roll is the same length all the way around and flat. - Adjust until you are happy with the amount of cuff showing (this looks especially great if you have a contrasting colored cuff).

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