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Adam Glassman
Photo: Patrik Andersson
Q: I own a lot of button-downs for work, and they're starting to bore me. How can I make them look less stuffy?


A: My tried-and-true trick is to turn up the collar—does wonders for the neck—and roll up the sleeves. By the way, it's incredibly smart to make the classic button-down your go-to top: It's innately chic and available at all prices (so you can stock up without losing your shirt). 

More ways to play it


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From the September 2009 issue of O, The Oprah Magazine
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