How to Roll Up Your Shirt Sleeves – Men Style

How to Roll Up Your Shirt Sleeves – Men Style

How to Roll Up Your Shirt Sleeves

Rolling one’s shirt sleeves is not something many men do with intention, but this seemingly simple habit can have a big impact on your look. So in this guide, we’re going to discuss a few methods on How to Roll Up Your Shirt Sleeves when you still want to look elegant and how to avoid looking like you’re ready for a fistfight.

History of the Rolled Sleeve

Men are rolling up their sleeves before hitting an opponent is the old cliche from movies and television shows, but there are many legitimate reasons to consider rolling your shirt sleeves up. It may be to avoid getting them dirty, wet, or stained, or to cool off on a hot day. Nowadays, a rolled shirtsleeve is often employed by high-level executives and politicians in an attempt to portray that they are an everyday guy. Clearly, rolled shirtsleeves can make a statement.

For many years it was considered poor etiquette to roll your sleeves.

Part of this was because it looked sloppy for an elegant gentleman to roll up his sleeves, part was due to the protection the shirt sleeve gave from the coarser fabric of the tailcoat or morning coat, and finally, it was because it really didn’t make a difference. The coat worn over the shirt was far bulkier, and it was in poor taste to remove one’s jacket before retiring at home.

History of the Rolled Sleeve
Short sleeve dress shirts are a huge fashion faux pas – don’t wear them!!

Short sleeve dress shirts are a huge fashion faux pas – don’t wear them!!

However, when the prep trends hit the Northeast United States and affluent young men were rebelling against their fathers who wore suits to check the mail, it became less important to keep a jacket on. It was a regular sight on college campuses for men to be seen with their blazer draped over their arm. It was a way to beat the heat in the summer, look cool with strong forearms showing and separate their style from the men who didn’t remove their tie until changing for bed.

What initially began decades prior to the working class was gradually becoming a trend in the affluent ivy league schools. Soon it wasn’t just being done outdoors. The trend continued, and as Hollywood stars like James Dean and Steve McQueen wore their sleeves rolled up, it became a way for the dapper preppy to look masculine, of-the-moment, and perhaps even a bit tough.

Today, rolling up your sleeves is done for a few reasons.

  1. It keeps your sleeves clean if you have to play in the dirt, or prevents them from getting wet; when washing your hands or cleaning off your car.
  2. Keeps you cool on a hot and humid day.
  3. A style faux pas to wear a short sleeve dress shirt; but not a dress shirt with rolled sleeves
  4. It will be a more formal outfit casual if the venue changes; such as going from the boardroom to a bar for drinks with friends.
The Dos and Don’ts of Rolling Up Your Sleeves
What not to do vs what to do

The Dos and Don’ts of Rolling Up Your Sleeves

The Dos of Rolling Up Your Sleeves
Remove your cufflinks before rolling your shirt sleeves


  1. DO embrace a wrinkle here or there. It shouldn’t look like the shirt has been cuffed and you bought it that way.
  2. DO keep the sleeve rolled up to the forearm or just above the elbow. No higher or lower for a dress shirt, or it is simply the wrong choice of shirt.
  3. DO fold your sleeves. It minimizes wrinkles and looks more polished and less sloppy.
  4. DO keep the sleeves even. Don’t leave one-two inches lower than the other.
  5. DO undo any buttons or remove the cufflinks before you fold.
  6. DO remove your vest if you have one on.


  1. DON’T leave your shirt sleeves folded while wearing a jacket over top.
  2. Avoid roll up jacket sleeves unless you’re deliberately going for the Miami Vice look.
  3. and DON’T just shoves the sleeves up. Avoid having random buttons sticking out or the cuff hanging off your arm.

When and When Not to Roll Your Sleeves Up

When and When Not to Roll Your Sleeves Up
President Obama projecting a casual appearance with his typical rolled dress shirt

When to Roll Your Sleeves

It is acceptable to roll your sleeves up when:

  1. You need to protect your sleeves from water, dust, or dirt such as washing your hands; helping to move office furniture, or rendering first aid
  2. It is hot or humid and you’re outside
  3. Eating foods that could easily make a mess such as crab legs, a hot dog, or a hamburger at lunch.
  4. When transitioning to a casual atmosphere in business attire; such as meeting friends or your date at the pub or coming home to your family; without having time to change.
  5. While spending time with your children or pets before and after work.
  6. When in the privacy of your own office with the door closed.
  7. While commuting or traveling.

When to Roll Your Sleeves

It is wise to avoid rolling up your sleeves when:

  1. You are in a formal office environment.
  2. During any interactions with your boss or a client.
  3. In any type of meeting, including dinner meetings or luncheons (at which point you should skip messy food anyway)
  4. When wearing any other garments on your upper bodies such as a jacket or a vest.
  5. At any formal or somber event such as a wedding, funeral, or even a cocktail party.
  6. When wearing a black tie, white tie, or morning wear.
when to avoid rolling up your sleeves
Be careful of body language as rolling a shirt sleeve can be seen as an aggressive move

How to Roll Your Shirt Sleeves

There are many techniques that offer various looks. Here are three methods we recommend because they’re slightly more stylish and elegant than the rest.

How to Roll Your Sleeves
A well-folded cuff

The Classic Fold

For years, the U.S. Marines have rolled their sleeves. Unlike other folds, the Marine-style cuff is done on purpose, ideally before you put the shirt on. We rarely recommend this as it’s not elegant to wear your collared shirt rolled up all day. If that’s the case, there’s no point in wearing business attire. Just put on a polo shirt and call it a day.

How to Roll Up Your Shirt Sleeves

However, if you have the privacy and the need to roll up your sleeves – and you’re wearing an undershirt – quickly remove your shirt and consider the Marine cuff.

  1. This only works with a shirt that isn’t wrinkled. Just as you would place the sleeve while ironing it! flatten out the sleeve on a clean table such as your desk or a dry restroom counter.
  2. At the seam where the cuff of the shirt begins; and with the buttons unfastened; fold the sleeve up with the stitching of the shirt cuff. As the seam, so the inside of the cuff is now facing out.
  3. Straighten the fold, making sure both the bottom and the top are straight and flat.
  4. Repeat the same process and fold it up once more, duplicating the initial fold.
  5. Straight it out and put on the shirt.
The Classic Fold - rolled sleeve
A Marine with his rolled sleeve


The Italian Method
Casual Italian roll

The Italian Method

This style works very well with fashion-forward dress shirts that use a contrasting fabric for the inside of the shirt’s cuff. It adds a bit of sprezzatura to the look and is understated but noticeable at the same time.

  1. While wearing the shirt, unbutton the cuff and fold it so the cuff is roughly an inch past your elbow. This should be a fairly long fold as you are only folding it once.
  2. Next, flip the bottom of the sleeve closest to your hand over; so it creates another fold and shortens the length of the rolled cuff. However, make sure that you only roll it about an inch less than the first roll. This way, about an inch of the sleeve’s cuff, will poke past the fold. This adds layer and dimension to the roll; and showcases a glimpse of the lining’s fabric to add a bold dash of flair to your outfit.
The Quick Roll
How to quickly roll your sleeves

The Quick Roll

This is ideal for a quick trip to the restroom; where you need to wash your hands; or if you’re worried about mustard hitting your sleeve; after getting lunch from the hot dog cart by your office.

  1. Undo all the buttons on your sleeve.
  2. Turn the cuff up just under your elbow! and then fold the edge of the cuff by flipping it down into the cuff so it’s tucked in.
  3. Roll the sleeve up by flipping folding it over itself.

This style is far more casual but is quick and easy to do in a time crunch. We don’t recommend doing it for long periods of time, though.

Nicely folded sleeve

How to Avoid Wrinkles In Shirt Sleeves

The finer the fabric and the quality of the shirt, the more you have to worry about wrinkles. Here are a few tips to ensure you don’t get wrinkles that will be noticeable after unrolling your sleeves.

  1. Never keep your sleeves rolled up longer than necessary. Immediately unroll them once you no longer need them cuffed.
  2. Don’t leave buttons fastened or cufflinks in when rolling your shirt.
  3. Rather than actually rolling the sleeve, fold it and make sure it’s neat and not creased or bulging.
  4. Also, Never hang up a shirt or launder a shirt that is still rolled.
  5. Make sure the shirt isn’t wrinkled prior to rolling up your sleeve.appear

How to Roll Up Your Shirt Sleeves – Conclusion

Now you know how to roll your sleeves up properly. The three techniques, if done properly, should give you a sharp roll without sliding down or appearing sloppy. Just remember not to do it regularly with high-quality dress shirts; as any rolling will stretch the fabric slightly with each fold. How do you fold your shirts?