How to Roll Shirt Sleeves

If you know me, you may have noticed I’m not a big fan of long sleeves. There’s something that annoys me about the feel of a buttoned cuff around my wrist, which is ironic because these days long-sleeved shirts are pretty much my standard. Thus I’m relegated to constantly rolling my shirt sleeves. I’ll even shamelessly admit that sometimes I even leave them rolled and just put them back on the hangar like that. What can I say, I can be lazy.

With years of practice though, I’ve pretty much mastered the art. There’s a few different techniques; you can start by flipping back the cuff and repeating that in a fold, or you can fold the cuff in half, repeating that up your arm in more of a “roll” effect. I’ve tried them all and would really say, the choice is yours. I find the “roll” gives off a much more casual look, so I usually use it with a more workman-like shirt. Something chambray or plaid flannel. It’s certainly not something you want to be using on dress shirts, as you’ll be wrinkling the hell out of the forearm while compromising the cuff in the process. 

Recently though, I stumbled upon an article somewhere that claimed the “true” way to roll a shirt sleeve. I tried searching the web today in order to find it and share it, but I had no luck in turning it up (cheers to Gregg for finding me the article, which is here at Dappered. I have great readers). In any case, the process is simple (2 steps), works surprisingly well without leaving too many wrinkles, and achieves a fairly good balance between casual and dressy. Here’s my step-by-step recount of the process:

Start by unbuttoning the sleeve buttons. You should also be wearing the shirt, FYI.

What you're going to do is flip the cuff back, but then pull that along your forearm....

....like so, so essentially it looks like you've just pulled your sleeves back. It's hard to gauge how far back you'll need to go until you get in more practice, but I usually stop roughly when the cuff meets the crease in my elbow.

Then you "flip" that sleeve portion over the cuff portion. I say flip in quotations because it starts as a flip at this step....

....but towards the end, it becomes more of a tuck, as you tuck the cuff into the now folded portion. Play with it a little to smooth it all out (or not).

And here is the finished product on another shirt.

Thanks for reading,

MD