Photo: Robert Trachtenberg

This former public school teacher's mission: to provide underserved students in America's poorest communities with the best educations possible.

Adam Says: "Depending on accessories, this dress can go formal or casual."

"If you're playing with color, try red. It's now accepted as a neutral, even for day."

Ifeyinwa Says: "I have a favorite pair of red shoes I call my power heels," says Offor, whose negotiation skills have helped Teach for America raise nearly $40 million and expand to eight new cities in the past two years. "If I'm wearing something bright, I feel ready—so bring it!" Here, she goes for the bold, pairing a cap-sleeved dress with peplum ruffle and two chunky necklaces —a look equally appropriate for school visits and dinners with donors. "Black is a uniform," says Offor. "You have to spice things up every once in a while."

Let's Make a Deal
"Nothing gets done without building relationships. I'm willing to listen. If you want to rant and rave or feel like you just need to be heard, I can do that."

Cap-sleeved dress, Calvin Klein; $128. Necklaces, Ann Taylor. Cuff, Noir Jewelry. Heels, AMI Clubwear.

Next: A wild print gives some edge to a classic tweed jacket