How to Roll Up Dress Shirt Sleeves the Right Way

Rolling up your dress shirt sleeves isn’t just about staying cool — it’s a subtle detail that shows your personal style. Whether you’re at the office, out with friends, or heading to a casual event, the way you roll your sleeves can make you look either sharp and confident or messy and unpolished.

In this guide, you’ll learn the four most popular sleeve-rolling methods and expert tips to keep your look stylish and comfortable.

1. The Simple Roll

✅ Quick and casual.

How to do it:

1. Unbutton the cuff and gauntlet button (the small one halfway up the sleeve).

2. Fold the cuff back once, inside out.

3. Continue folding until the sleeve sits around your forearm or just below the elbow.

Best for: Casual outings or when you need a quick, no-fuss style.

2. The AIFA Roll (Italian Roll)

✅ Neat and stylish with less bulk.

How to do it:

1. Unbutton the cuff and gauntlet.

2. Fold the cuff once upward, covering it completely with fabric.

3. Adjust the roll so it sits just below your elbow.

Best for: Modern office settings, evening events, or when you want a sleek, tailored look.

3. The Master Roll (J. Crew Roll)

✅ Professional and secure — won’t slip.

How to do it:

1. Unbutton both cuff and gauntlet.

2. Fold the cuff upward so it reaches about two cuff lengths above your wrist.

3. Take the bottom edge of the sleeve and roll it upward again, tucking the cuff halfway under.

4. Leave the top of the cuff peeking slightly for a stylish touch.

Best for: All-day wear, offices with a business-casual vibe.

4. The Marine Roll (Military Style)

✅ Sharp, structured, and practical.

How to do it:

1. Fully unbutton the cuff and gauntlet.

2. Flip the cuff inside out and pull it above your elbow.

3. Fold the fabric upward in equal sections, covering the cuff completely.

Best for: Work that requires movement, or a clean, disciplined look.

Pro Tips to Keep Your Look Sharp

• Iron first: Wrinkle-free sleeves make rolls look cleaner.

• Mind the length: Sleeves should stop at or just below the elbow. Anything higher looks sloppy.

• Match the occasion: Go with the Master or AIFA roll at work, Simple or Marine roll for casual settings.

• Quality fabric matters: Higher-quality shirts hold rolls better and look more polished.

Rolling up your dress shirt sleeves is a small detail that makes a big impact. By mastering these four techniques — Simple, AIFA, Master, and Marine — you’ll always look sharp, stylish, and ready for any occasion.