What 50 Looks Like

Christie Brinkley, 57

The one-time Sports Illustrated model has managed to maintain her all-American radiance through a vegetarian diet and plenty of exercise. To accentuate cheekbones, which gravity can't touch, Rose-Marie Swift, creator of RMS Beauty, recommends going slightly lighter than Brinkley's spotlight-ready version. Try a cream formula, which is easier to control than powder and will give skin a dewy glow.

SEARCH: See Brinkley in her Broadway musical debut earlier this year

Michelle Pfeiffer, 53

"Less is more when it comes mature skin," says Swift of Pfeiffer, who opts for minimal makeup and instead glams up her look with tousled curls.

Iman, 56

At 56, Iman has the same glow that first lit up the catwalks 30 years ago. Sonya Dakar, owner of Sonya Dakar Clinic in Beverly Hills, says that women her age should exfoliate three times a week with a gentle peptide cleanser for radiant skin.

SEARCH: Find affordable and effective exfoliating cleansers

Rita Wilson, 55

As one half of Hollywood's most loved couple, Wilson still has that girl-next-door charm, even at 55. Subtle highlights and neutral makeup make her look effortlessly pretty.

Oprah Winfrey, 57

"Oprah's makeup always looks spot-on for who she is and what she stands for," says Swift. "She leans toward a sophisticated strong eye, while her blush is always the right color and her lips never overpower her look."

Bo Derek, 55

She once broke hearts running down a beach in a red bathing suit and cornrows. Now 55, Bo Derek represents the new Golden Years.

SEARCH: Which former Sex and the City hunk has been Bo’s beau since 2004?

Annette Bening, 53

"To me, Annette Bening is a woman who is growing older with elegance and grace," says Swift. "Her makeup is simple and clean, and she doesn't try to look like anyone other than herself."

Angela Bassett, 53

Swift says that light-reflecting qualities in makeup can help make skin of any age look youthful. Here, Bassett's shimmery shadow helps her eyes sparkle.

Madonna, 53

Over the years, Madonna has emerged as a style icon, with a look that has evolved from punk in the '80s to polished today. "Her healthy diet and exercise routine have definitely paid off," says Swift.

SEARCH: Has Madge had work done?

Kim Basinger, 58

Although nearing 60, Basinger still looks as beautiful as she did in her steamy 9 1/2 Weeks role. Rumor has it that she keeps her skin toned and smooth thanks to a collagen therapy gel.

SEARCH: Find out how collagen therapy gel works

Rene Russo, 57

Layering heavy makeup on aging skin builds itself into fine lines and dries skin out after a few hours, says Swift. Rene Russo still manages to keep it natural with some mascara, nude gloss and a hint of blush.