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).
Layered: A pink shirt (Lands' End, $45) and slim-fitting vest (Brooks Brothers, $148)—the argyle is straight out of Love Story—look preppy. Draped with a necklace of netting- covered beads (Sequin), they become sophisticated rather than schoolgirlish.
Cinched: The ultimate chameleon, a black shirt (Thomas Pink, $180) looks good all day—never gets grubby—and moves easily into evening. Dress it up with a wide, waist-emphasizing belt (Devi Kroell) and a bold, colorful necklace (Aldo).
Pinned: Take a plain white shirt (Theory, $190)—I like them slightly shaped, with a bit of stretch—and change the buttons to high-contrast black (M&J Trimming). Add a floral brooch (Mina Mann) and you've got instant charisma.
Wrapped: Menswear patterns like the stripe on this shirt (Thomas Pink, $195) could use some excitement. Choose a big, fringed scarf (Madewell) in an ethnic pattern that uses the same palette as the shirt; loop it loosely around your neck.