28, middle school teacher New York City
Before: "Leggings and flowy tops have been my uniform for the past few years," says Nicholas.
Nicholas took a two-year hiatus after her daughter, Jayla, was born in 2009. "Before I had a baby, I never thought I'd stay home," she says. "But it was the more affordable option for my husband and me."
Why She was Ready for a Change
With Jayla in preschool, Nicholas was ready to work again. "Teachers are in front of young people every day—we need to look our best."
Her New Look
A pencil skirt, dotted top, and pink blazer are polished without stifling her creative style. Lighter haircolor warms Nicholas's complexion. "I'm very artsy and bohemian. I like that this outfit is pulled together but still has a bright color," says Nicholas.
What You Can Learn
Don't be afraid to break up a suit: Pair the jacket with khakis or top the skirt with a printed button-down. "That way you won't look too matchy," says Glassman.
Skirt, South, $87, Very.com. Top, Tory Burch, $350, ToryBurch.com. Blazer, Banana Republic, $130, BananaRepublic.com. Earrings, Melanie Auld, $210, MelanieAuldDesigns.com. Necklace, Sonyarenée Jewelry, $48, SonyaRenee.com. Cuff, Sibilia, $158, Sibilia-Accs.com. Shoes, Kenneth Cole New York, $168, KennethCole.com for stores.