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How to Roll Your Shirt Sleeves (The Right Way)

BY Buffalo Jackson Insight
BY Amanda Uher

Back in the day, a man would roll up his shirt sleeves to kick back after a long day... or to do manual labor… or to get ready to fight… or to just cool off. Today, the same reasons can apply, but more often, sleeve-rolling has become a style statement. Clearly, when to roll your shirt sleeves can vary quite a bit. To help in any situation, we’re sharing a few variations on how to roll your shirt sleeves so they are comfortable and still look great.

The Cuff

The Cuff—a.k.a. the “one and done”—is the quickest roll, and look best when pairing a collared shirt with a pullover sweater.

1.  Unbutton the shirt sleeves of your collared shirt.

2.  With both the sweater on and the collared shirt underneath, tug the sleeves of the collared shirt down so they’re hanging below the end of the sweater sleeves.

3.  Turn the cuff of the shirt sleeves up one time, overlapping the ends of the sweater sleeves.

4.  You may re-button the cuffs of your shirt sleeves for a more tailored look, or leave them unbuttoned.  

The Casual

The Casual roll is a simple, classic way to roll your shirt sleeves, and is well suited for chambray and flannel shirts. This roll, like the Cuff, also works well when combining layers.

1.  Begin with shirt sleeves fully extended and unbuttoned.

2.  Flip the cuff up once, turning it inside out.

3.  Fold once more, hiding the cuff.

4.  This should shorten the sleeve by about a third, or to around the middle of your forearm. Stop rolling here, and be sure the corners of the cuff are tucked neatly into the fold.  

The Italian

The Italian roll is the least constricting and is a particularly good choice for shirt sleeves with a contrasting lining on the inside of the cuff.

1.  Begin with shirt sleeves fully extended and unbuttoned.

2.  Flip the cuff back and inside out, but then continue to pull the flipped cuff up to just below your elbow. The result is one long fold, with the bottom portion of your sleeve turned inside out.

3.  Take the bottom of the inside out portion and fold up in another single fold, trapping most of the inside-out cuff in the top.

4.  Be sure to leave a portion of the inside-out cuff showing (up to about a third), especially if your cuff has a contrasting lining.  

Most importantly, before you worry about how to roll your shirt sleeves, be sure you begin with a great shirt. No matter how you roll, a collection of classic, well-made men’s shirts will serve you well.  

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