On the Effortless (Looking) Sleeve Roll

The men behind Gilt MANual answer your most pressing style questions.
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Howard Dean Rolls Deep

What are some ways that I can achieve natural looking rolled-up sleeves? The way I do it looks way too “prepared.” Thanks.

Not wanting to look too fussy—hang on to that. It’s a solid impulse across the board. Your predicament reminds me of a brief how-to item that appeared in a certain men’s shopping magazine that was briefly on the scene in the mid 2000s. The goal of the piece was to show dudes a super fresh new way to roll up their sleeves, and I’ll never forget chucking the magazine across the room in frustration the moment I first read it. The piece has since become a running joke between myself and MANual contributor Euan Rellie on how not to talk to guys about style—because when it comes to the basics, it’s often best to stick with tried and true methods. (Yes, I know, we did recently run an item on how to roll up your chinos, but we tackled it, as we do many topics, with an arched eyebrow.)

Getting the look you want doesn’t require a new method as much as proper execution. The key is to keep the folds from getting too wide—they should be only slightly wider than the cuff itself. There are a brave few who like to fold a cuff in half before they roll, but to me that can come off as equally affected or prepared. The perfectly rumpled look you’re gunning for comes from three things: width of cuff, type of fabric, and positioning of the roll. If you want a narrower roll, buy a shirt with a narrower cuff. As for material, thicker oxford cloth is going to give you a more rumpled roll, while the finer broadcloth of most dress shirts creates a more crisp look. There isn’t much to be done about this, except to give your sleeve an extra flip, to just above your elbow. After your rolled-up cuff has spent an hour or so in the crease of your elbow, it’ll won’t look “prepared.” Of course, it’ll also look pretty wrinkly should you find it necessary to unroll and button back up.

This topic calls to mind another absurd style moment from the same era. During the 2004 campaign for the Democratic nomination, Howard Dean had made rolling up his sleeves past his elbows—working man style—his thing. This in turn forced each of his competitors to develop his own elaborate sleeve-rolling ritual. Because dammit, they were just as just as in touch with real folks as that straight-talking Governor from Vermont, and if elected they’d be just as ready to do some metaphorical sleeve-rolling, too. Kerry, who favored the more patrician double-flip, won the nomination, but Dr. Dean won on style points. (Though duty requires me to point out that his sleeves were a little blousy.)

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  1. David says:

    The blousy sleeves are to distract from his crazed-eye look I think…

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