How To Roll Up Dress Shirt Sleeves in 3 Popular Styles

Dress Shirt Sleeve

When it comes to office temperature, there seems to be an unwritten rule that if one person is comfortable, another is either going to be hovering under a blanket or trying to take as many layers off as they can before they die of heatstroke. There is no in-between. If you are like most men you tend to be warmer when others are complaining that they’re cold.  The question is how do you stay stylish while not getting too warm at work?  

The most simple solution is rolling up your shirt cuff sleeves. The first rule of this is never just push your sleeves up! This technique will make you look unprofessional, unstylish, and sloppy.  Instead, use one of these 5 tried and true methods on how to roll dress shirt sleeves to keep you looking sharp!

When Should You Roll Your Shirt Sleeves?

Rolling your shirt sleeves is a practical and stylish solution for managing temperature and showcasing a more relaxed vibe. Here are some situations when rolling your sleeves is appropriate:

    • Casual Occasions: Rolling up your sleeves is perfect for casual gatherings, outdoor events, or relaxed outings with friends. It adds a touch of informality to your look without sacrificing style.
    • Warmer Weather: When the temperature rises, rolling up your sleeves helps you stay cool and comfortable while maintaining a polished appearance.
    • Manual Work: If you're engaging in manual labor or tasks that require physical movement, rolling up your sleeves prevents them from getting in the way and keeps them clean.
    • Showing off Details: If your shirt has unique cuff designs or contrasting colors, rolling up the sleeves can accentuate these details and add visual interest to your outfit.

Remember, the key is to roll your sleeves neatly and deliberately, avoiding a haphazard or sloppy appearance. 

What Does It Mean When A Guy Rolls Up His Sleeves?

When a guy rolls up his sleeves, it can signify several things:

    • Readiness for Action: Rolling up sleeves can symbolize readiness to tackle tasks or get work done. It's a practical gesture that suggests preparedness and a willingness to engage in physical activities.
    • Casual Attitude: Rolling up sleeves is often associated with a more relaxed and informal demeanor. It can indicate a transition from formal to casual settings or a desire to appear approachable and down-to-earth.
    • Comfort: In warmer weather or environments, rolling up sleeves is a practical way to stay cool and comfortable. It demonstrates adaptability and a preference for practicality over strict adherence to formal dress codes.

Overall, rolling up sleeves is a versatile gesture that can convey readiness, informality, and a desire for comfort.

How to Roll Up Dress Shirt Sleeves?

Sleeve Rolling Method #1: Aifa Sleeve Roll

For a more casual look the Aifa sleeve roll is the way to go! The only downfall is this roll tends to come undone a bit easier than the rest on this list. 

    1. Fold the bottom of the sleeve up the width of the shirt cuff.
    2. Using the same width, fold the shirt cuff over a second time.
    3. Do NOT smooth the fabric, this look is supposed to be very casual. 

Sleeve Rolling Method #2: High Sleeve Roller

For those men that have more muscular arms, the high sleeve roller is a great way to look stylish as well as show off the arms you work so hard on! It’s also great if you must do manual work!

    1. Lay the shirt down flat on a surface.
    2. Fold the sleeve up about the width of the shirt cuff. 
    3. Repeat step 2. 
    4. Roll the sleeve a 3rd and 4th time until the whole shirt cuff is covered.

Sleeve Rolling Method #3: Master Sleeve Roll

The Master sleeve roll is a great way to show off shirt cuffs that have great design or a different tone than the shirt.

    1. Pull the shirt cuff up so that it is about 2-4 inches above the elbow.
    2. Make sure to smooth out any wrinkles in the fabric.
    3. From the bottom pull the sleeve up so a little shirt cuff is still felt showing. 

The best part is that each of these rolls take less than 2 minutes of your time and instantly takes you from sloppy to sleek. No more messy sleeve pushes! Now that you have the techniques, it’s time to put it into action. DM us photos of your sleeve successes on our Instagram @Statelymen to be featured!




Sebastian O’Hara
Writer based in Los Angeles, CA