VIDEO: How to Roll Your Shirt Sleeves in 3 Easy Steps

easy peasy

By Megan Collins | Last Updated: Apr 22 2019

Want to learn how to roll your shirt sleeves? It’s as easy as ready…set…ROLL.

When it comes to clothes, it’s the little things that make a big difference.

Once you’ve nailed your personal style and figured out what a good fit looks like, that’s when the real fun begins. Seemingly small things like where your pants break truly levels up your whole outfit, or how your pocket square looks with your tie.

Maybe it’s the time I spent in college as a “visual merchandiser” (aka, mannequin dresser) for Abercrombie & Fitch. HQ would send books – literally, huge binders – every time the displays on the tables at the front of the store had to be changed. Every detail was called out and explained how to do just so. Every cuffed pant, every rakishly thrown open collar, every layered bracelet. No look happened by accident.

Maybe that’s why my eye flits to the excessive billowing of a dress shirt, or the topcoat with its vents still stitched closed. Not to say us ladies don’t make style mistakes (we do, constantly!), but I’ve come to believe that women are generally more aware these little styling tips and tricks from…well, from where? Working at the mall growing up? Maybe magazines? Probably most of all from trading tips with our friends.

“Hey, how do you make your hair do that swooping thing in front?” we might ask at brunch. “How did you cuff your pants to get them to stay that way?”

I can’t really see guys having these same conversations with their friends.

But here at SG HQ, we know that you do want to go the extra mile in dressing well because you know how confident you feel when you look and feel like a million bucks. So we’re here to help with those little things that take your outfit to the next level. Like what? How about a step-by-step primer on how to roll your shirt sleeves in a way that says, Just got finished shooting the J.Crew catalogue cover?

The thing about rolling your shirt sleeves is that it seems so simple, right? And it is. Literally anyone can simply roll roll roll your shirt sleeves up to, or even past, your elbows. But that doesn’t mean it looks good. In fact, a basic roll of your sleeves might be functional, but it’s definitely not fashionable.

In fact, rolling your shirt sleeves stylishly is an art. And today, we’re teaching you how to master it. After reading the tutorial and watching the video below, you’re going to be the Bob Ross of rolled shirt sleeves. But instead of happy trees, you’ll be rocking happy sleeves.

Spoiler? It’s all in the zhushing. Thankfully, this kind of elevated look doesn’t take much extra effort, and anyone – yes, anyone – can do it.

Below, how to to roll your shirt sleeves in a stylish way:

1. Unbutton your cuffs.

If your shirt fits looser on your arm, keep the gauntlet button (the next button up on your sleeve towards your elbow) buttoned to ensure the upcoming folds stay tight against your arm.

If the shirt hugs your arm more closely, leave it unbuttoned to allow the fold to go over your elbow without cutting off circulation.

2. Fold the shirt sleeve back

Right to the uppermost part of your arm where you eventually want the top of the fold to sit, usually a little above the elbow.

3. Fold this initial fold nearly in half

Bringing the secondary fold on top of the first. Be sure to leave the cuff on the original foldover peeking out. Tug at the ends a bit and rumple the material so it looks like you did it quickly. Even if you actually spent five minutes zhushing it to get it just so.

…and 4. Open cold beer

Sip, then bask in your nonchalant, elegant look. Prepare to welcome admiring glances from women, small children, and the elderly in surrounding vicinity.

Want a more dynamic visual?

Check out this video on how to roll your shirt sleeves that makes the process crystal clear:

For those of you who are visual learners, hopefully this helps! We figured, if it’s useful to see it in pictures, it would be even more helpful to watch it all unfold…or actually, watch it fold  [insert groan here].


Wait, one more thing!

Here’s how to roll your short sleeve button up shirts.

The short sleeve button up is at the top of our shopping list for warm weather. They’re the perfect overlapping section of a Venn diagram between long sleeve button up and basic tee, so it’s hard not to fall in love with these shirts.

But there’s a little something extra you guys can do that makes this already awesome shirt sooo much better. Not sure why, but there is something so undeniably attractive about rolling up short sleeves.

It could be the little glimpse of where the deltoid meets the bicep exposed by a higher sleeve, or it could be the bad boy vibe it gives off, even without the pack of cigarettes stuffed inside. Whatever it is, rolling the sleeves takes this style of shirt from Dwight to James Dean. It even looks good with regular tees!

Since the short sleeve button up is going to be a regular in your spring and summer wardrobe (if it’s not already) this should help. Just follow the steps in the pics below and voilà, you’ll be a spiffy springtime stud.

There are two ways to roll a short sleeve: neat and disheveled.


1. Cuff the sleeve with the hem of the fabric

2. Roll once, keeping the same width of the sleeve hem


1. Roll tightly and haphazardly (approx. 3 rolls)

There you have it! Now you know how to take your short sleeve button up to the next level.


Still feeling overwhelmed? SG can help

If you’re ready to upgrade your style but dread the thought of shopping for them…consider having Team SG shop for you! We’re obviously biased, but we swear it’s really great!

Let us rescue you from shopping fatigue and sartorial apathy. We can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are! Ready to seriously improve your closet and your confidence? Give us a shout.