Achieve Your Dream Look: Stunning Style Transformations

Jocelyn Ruggiero, 39

Real life: Writer and performer, mother of twins
Secret alter ego: Pinup girl

Dresses for comfort, and never fusses with her natural color or curls.

Why she believes she was born 50 years too late:
"I've always liked the idea of a little tease. There are so few things that are left unsaid these days."

When she first fell for Rita Hayworth, et al.:
"I was so young, I can't even remember. I grew up hanging pinup posters in my bedroom."

How she brings the '40s into her 2012 life:
"I listen to Billie Holiday and Ella Fitzgerald. And I wear red lipstick nearly every day."

How she doesn't:
"I recently moved to suburban Connecticut and have gotten more casual. I wear a lot of jeans, vests, and sneakers."

The Hair

Jocelyn has always dreamed of going Hayworth-inspired red but worried the results would look unnatural. Stylist Alexis Kuykendall, from the Ken Paves Salon in Beverly Hills, chose a rich auburn without the copper or orange tones that can make red look fake. With Jocelyn's naturally curly hair, the rest was easy. Stylist Roberta Rogers from Ken Paves used a large-barrel curling iron to smooth her waves and a styling cream to keep them shiny.

The Makeup

Though Jocelyn was already at home with the red lipstick of a '40s starlet, Rebecca told her to retire her usual blue-based reds in favor of warmer, more orange-toned shades (like the Yves Saint Laurent Rouge Pur Couture lipstick in Le Orange she's wearing here). "Orange-reds won't emphasize the ruddiness in Jocelyn's skin the way blue-reds can," she says. With bright lips, eye makeup should stay simple: Jocelyn's eyes are defined with a medium brown shadow in the crease, black liquid liner along the upper lashline, and two coats of mascara.

The Clothes

This formfitting L'Wren Scott dress is instrumental in playing out Jocelyn's fantasy: The strapless, curvy fit says pinup, while the below-the-knee length leaves a bit to the imagination, Adam points out. The only accessory needed: flirty, polka-dot retro platforms (Jessica Simpson Collection).

Your Inner Pinup

Ava, Betty, and Lena always paired bold lipstick with flawless skin. Get it fast: Mix a liquid foundation with a little bit of water to even out your complexion without a dry or cakey finish.

Forties-inspired clothing is all about the silhouette: Off-the-shoulder, strapless, and waist-enhancing pieces are key, and the fit should be body-conscious but not skintight. Choose bright colors and—if you want to be extra-playful—fun patterns, like cherry or bird prints.

Dress, L'Wren Scott, $2,990, by special order, Barneys New York, 888-822-7639. Shoes, Jessica Simpson Collecteion, $110, jessicasimpsoncollection.com.