Look Smaller in Skirts!
Big, crisp skirts make your waist look tiny, flatter broad hips, and produce a satisfying swish. Try one in floral taffeta (Jason Wu, $1,300), but keep it casual with a fitted turtleneck in a coordinating stripe (Vince, $85). Mad Men costume designer Janie Bryant is a stickler for historical accuracy, so January's character is polished on the outside—"She dresses up to go to the market!"—and authentic right down to her undergarments (her bras have tips for a pointy effect).
Complement this casually sophisticated look with fresh, flawless skin and bold, matte lips. To get a creamy complexion, brush on either a matte-finish liquid foundation (try Shu Uemura Face Architect Smoothing Fluid Foundation) or a mineral powder (like CoverGirl TruBlend Pressed Mineral Foundation), says Christy Coleman, the makeup artist for this story. For a Grace Kelly mouth: Outline your lips with a liner that matches your natural lip color, and then blend to soften the edge. Finish with a matte, coral-tinted lipstick (like YSL Pure Lipstick in Rosy Coral).
What Would Grace Do? Dress Your Waist
An impressive 34-24-35 during her years as a star, Grace highlighted her measurements with clothes that accentuated her waist. You can channel Lisa Fremont, her high-society working girl character in Rear Window, and wear a belt to cinch your midriff.