Stephanie Wilson

Owner of Wicked Creative public relations, age 38; and son, Teo, age 1½

Style icons: Jennifer Aniston, Adrian Grenier and Justin Timberlake.

What they’re wearing now: (Stephanie) Alice + Olivia dress and Christian Dior heels; (Teo) Did Too button-down shirt, Krickets black pants with suspenders, Sovereign Code vest and Converse tennis shoes.

Wilson runs her public relations company with a certain set of style rules. “Always look polished, don’t wear anything that is too tight and watch the hemlines,” she says. But when it comes to her son, Teo, she’s a little more playful. “He is my little BFF, so a lot of times I’ll dress us to complement each other. A navy blue shirt to match a navy blue dress, or I’ll wear my white Chucks in contrast to his black ones. But, nothing that will humiliate him too much.”

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Style icons: Brigitte Bardot, Mary-Kate and Ashley Olsen, Leandra Medine (blogger: The Man Repeller), Scott Schuman (blogger: The Sartorialist), Rachel Zoe. What she's wearing now: Gucci shirt, Rich & Skinny jeans, Pour la Victoire heels, Moschino for Target belt, SierraMaryDesign cuff, The Jeweler's Daughter Snake and Heart rings, Chevron bracelets, Ampersand and Stardust Necklaces, and various estate pieces.