How to Roll Up Dress Shirt Sleeves: 5 Different Ways

Gone are the days when you’d only roll up your sleeves to prepare for some serious work, like changing a flat or repairing a leaky faucet. Obviously, rolling up your sleeves is a great way to get some relief on hot days. But rolled sleeves also provide a fashion-forward look when you want to express a sophisticated casual vibe.

This guide covers five shirt sleeve rolling techniques that aren’t only functional but stylish. Instead of simply trying to get your cuffs out of the way, confidently learn how to roll up dress shirt sleeves for some fashionable panache.

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The Classic Roll

The Classic Roll is simple and easy to manage while still being appropriate when you’re relaxing after more formal occasions. When you go with the Classic Roll, you exude a sense of stylish ease. Just make sure both sleeves are rolled to the same length.

1. Unbutton your cuffs and any gauntlet buttons (the open placket above the cuff).
2. Fold the cuff back, inside out.
3. Continue to fold the cuff back two times, until the middle of your forearm is exposed and then tuck the corners of the cuff neatly into the fold.

The Master Roll (A.K.A. Italian Roll)

If you want to know how to roll dress shirt sleeves for a more polished look, the Master Roll is for you. Although the Master Roll appears effortless, the look is more purposeful, especially if your sleeves have an interesting contrast lining. Another advantage to The Master Roll is that you can roll your sleeves back down with minimal wrinkling. This is one of the less restrictive rolls which allows for comfortable arm movement.

1. Unbutton your cuffs and the gauntlet buttons.
2. Pull the cuff and sleeve fabric up your arm about two cuff widths, then smooth the fabric.
3. Pull the remaining sleeve fabric up to cover over most of the cuff.
4. Leave up to a quarter or third of the cuff showing.

The Casual Roll

The Casual Roll is laid-back, uncomplicated and can even appear slightly rugged. This is a simple roll that can be accomplished quickly and spontaneously — ideal for smart-casual settings.

1. Unbutton your cuffs and any gauntlet buttons.
2. Pull the cuff back, turning it inside out.
3. Fold the cuff over just one time so that the sleeve fabric hides the cuff.

The High Roller

If you anticipate a dirty job ahead, need to manage some heavy lifting, or just want to look casually cool, try the High Roller. This roll gives you maximum mobility to move your arms plus allows your sleeves to stay clean.

1. Unbutton your shirt cuffs and any gauntlet buttons higher up the sleeve.
2. Pull the cuff back, inside out.
3. Fold the cuff once again, allowing the width of the cuff to determine the size of the fold.
4. Fold the cuff a third time (maybe a fourth if you have long arms) so that the sleeve ends above your elbow. Tuck any excess fabric in the fold for a clean look.

The J. Crew Roll

J. Crew’s classic styles have a cool and casual edge that translates to their effortless-looking sleeve roll. Check out this J. Crew spin on how to roll up sleeves on a dress shirt:

1. Unbutton the cuffs and any gauntlet buttons.
2. Pull the cuff inside out, all the way up to where your elbow bends.
3. Roll the bottom of the remaining sleeve fabric up to cover the cuff.
4. Pull out the outside edge of the cuff just a bit for an effortless-looking rolled cuffed sleeve.

Tips for Choosing the Right Roll

• Choose the Right Roll for the Right Setting:
  • The Classic and Casual Rolls are ideal for casual settings.
  • Go with the Master Roll or the J. Crew Roll for semi-formal occasions.
  • The High Roller is a great choice if you need to roll up your sleeves for dirty or heavy work, or if you want to show off your toned arms, your tattoos, or just look fashionably cool.
• Choose the Right Roll for the Right Fabric:
  • Heavier fabrics like flannel work well with high rolls.
  • Lighter fabrics like cotton and linen are easier to fold and will remain rolled with the Master Roll or the J. Crew Roll.
• Avoid an embarrassing fashion faux pas — don’t roll your shirt cuffs up over your jacket sleeves.

No matter which sleeve roll you choose, you’ll achieve your best look when your dress shirt fits correctly. Refer to The Tie Bar’s Dress Shirt Size Guide to find the best-fitting dress shirts.

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Balance function and flair — whether you’ll be rolling up your sleeves for some relief from hot weather, or rolling them to achieve a fashion-forward look — it’s easy to master each of the sleeve rolling techniques. Just make sure you start with a great-fitting dress shirt to ensure your rolled sleeves look functional and stylish.

Review our guide to feel confident about selecting the right sleeve roll for your shirt and the particular setting. The Classic and Casual Rolls are terrific choices for laid-back casual occasions. If you’ll be loosening your tie and rolling your sleeves after a business meeting or formal affair, the Master (Italian) or the J. Crew Rolls will provide fashionable flair.

Be sure to explore The Tie Bar’s collection of beautiful and handsome dress shirts to find the perfect fit for your preferred shirt sleeve rolling style.

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