Adam: "Tell your daughter to mind her own wardrobe. A free-spirited style is fine as long as it's age-appropriate. To look hip but sophisticated, slip in a few rock 'n' roll elements (Sgt. Pepper–esque velvet jackets, skinny jeans, boots, leather, anything studded) while keeping the rest of your outfit subdued. Or, do a more subtle "downtown" look—dark colors, unconventional shapes, touches of metal."

Fine details—nailhead-studded boots (Stuart Weitzman) and a fringed nickel-coated brass necklace (Burberry Prorsum) add personality to the basic black dress (Zero + Maria Cornejo) worn by Regina Mumme Whitaker, 49, a mother of two. 

Scarf, Zero + Maria Cornejo. Tights, Hue.

Purple reigns when it comes to this quilted, quasi-military velvet. Gray jeans—yours needn't be as narrow as those on writer Damasa Doyle, 34—ground the strong piece (jacket, top, and jeans, L'Wren Scott).
 
Shoes, Christian Louboutin for L'Wren Scott.