On the June 1995 cover of ESSENCE magazine, her very first for us, the supermodel was stunning in kohl-rimmed eyes and berry lipstick.
Decked out in smokey blue eyeshadow, flawlessly defined brows and a flirty pony, Cynthia Bailey attended the Sports Ball benefit dinner with date, basketball player Jayson Williams.
On her second ESSENCE cover, Bailey smoldered in creamy, earth-toned makeup.
Rocking a smokey forest green eye, coral lipstick and a sassy fedora, Bailey attended the ‘A.I. Artificial Intelligence’ premiere with her then-boyfriend, actor Leon.
At the “Brown Sugar” premiere, Bailey hit the town in a wash of teal shadow and a coffee-toned lip. So pretty.
With her lush pewter eyeshadow, neutral lip and white tank, Cynthia Bailey sported a sexy, tough chic look at the “Honey” premiere.
Cynthia Bailey hit a New York City party sporting flawlessly defined brows, rosy cheeks and a neutral lip.
With her vampy smokey eyes, crushed-berry cheeks and high-shine gloss, Bailey looked every inch the glamour girl at an Atlanta Christmas gala.
Rocking winged navy eyeshadow and a fierce white manicure, Bailey and her hubby Peter Thomas attended Ted Turner’s Captain Planet Cartoon 20th Birthday benefit.
At the 2010 Winter Ball in Atlanta, Bailey made a major makeup statement in a seriously defined brow and smokey, sultry eyes.
In 2010, Bailey attended a Spelman College benefit concert rocking an impeccable face of makeup: Khol-smudged eyes, rosy cheeks and sheer, raspberry glazed lips.
During an appearance at the ESSENCE Music Festival, Bailey wowed the crowd in a smokey plum shadow and a sheer bronzey-berry lip.
Bailey hit the Dennis Basso Fall 2011 fashion show rocking cobalt blue-lined eyes and cinammon-kissed cheeks.
At the Vivienne Tam Fall 2011 fashion show, the supermodel went for a dramatic look with a wash of deep blue shimmer shadow and a raspberry cheek stain.
At the Steve Harvey Foundation Gala at Cipriani, Bailey worked a Cleopatra-esque makeup look with feline eyeshadow, and a copper-hued lipgloss that enhanced her skintone.
During a visit to the ESSENCE.com offices, Bailey looked girl-next-door cute in lush lashes, burnished gloss and soft waves.
At the Victor De Souza Spring 2012 fashion show, Bailey dazzled in a metallic aqua eyeliner and come-hither crimson lips.