O creative director Adam Glassman—who dressed Oprah in pieces under $100 for this month's cover—has been hankering to do this for a long time. "Readers always love our 'Great Buys Under $100!' and I've been wanting to get Oprah in on the fun," he says. Oprah, who loves a good bargain, was instantly game. "She doesn't limit herself to high-end or pricey pieces," Adam says. "They just need to fit well—and make her feel beautiful."