4 of 4
Judson O'Hair, 41
Technology Sales Executive
"The vixen in me was never really…encouraged," says Judson, recalling the kilt-and-kneesocks uniform of her days at a girls' school, the bulky sweaters of her college years in Vermont, the conservative crewnecks she currently favors when she calls on her (mostly male) clients. "I haven't done the whole 'sexy' thing—until today." But for a first-timer, she was a natural, hardly flinching as Ken transformed her simple shoulder-length hair ("It's always been a variation on this theme," she says) into a glamorous bob, stacked in the back and with side-swept bangs in the front, to bring more focus to her deep brown eyes. "The silhouette reminds me of Faye Dunaway's style in Bonnie and Clyde," Ken says. "All the edges are soft, but the overall effect is still bold, daring."

Our fashion editor said the same about the next step in Judson's vixenization: sliding into a curve-hugging, cleavage-baring silk jersey dress. To balance the sophisticated haircut and clothes, Rebecca kept the makeup understated, blending a warm beige shadow over Judson's lids and smudging a light brown one along her upper lashline. Then she tapped on a pink lipstick to leave a raspberry stain on her mouth. Once the transformation was complete, we wheeled in a plush, unmade bed; Judson hesitated only for a second before she hopped in (rhinestone-studded stilettos and all). After her roll in the sheets, she reflected on her foray into "the whole 'sexy' thing": "I've always thought of myself as the perky, fun girl, the goofball; suddenly, I feel powerful."

A few days later, she called to give us an update after a client meeting. "The guys didn't even notice any difference," she said. "But somehow I felt more serious, more grown-up. I'm definitely going to keep up this cut."

Dress, Zac Posen. Earrings, De Beers. Ring, David Yurman. Bracelet, Whiteflash.

Jenny Bailly