39, television producer, bakery owner New York City
Before: "I owned a couple of things that were not black—and I think they were pajamas," says Ahmad.
"My suits were almost always black," says Ahmad, who used to work as a Wall Street banker. Now her projects include developing and hosting a children's TV show and mobile app about global food, and opening a bakery.
Why She was Ready for a Change
"I wanted to dress more creatively," she says. "If you want people to follow you on an adventure, a black suit's not going to cut it."
Her New Look
A colorful button- down is fun and kid-appropriate; teal jeans are a fresh alternative to regular denim, says Glassman. "I would never have combined these pieces, but by the end of the day I was dancing in this outfit!" says Ahmad.
What You Can Learn
"Experiment with color and prints, but stick to silhouettes that flatter you," says Glassman. "Layered jewelry is another great way to personalize your look."
Shirt, DKNY, $169, DKNY.com. Jeans, JAG, $79, JAGJean.com. Earrings, Meghna Designs, $250, MeghnaDesigns.com. Bracelets, Bounkit, $344 with code OPRAH, Bounkit.com. Ring, SKU Jewelry, $348, MaxandChloe.com. Shoes, Charles David, $185, 310-659-7110.
Next: What to wear when you've gone up or down a size