Bethenny Frankel's Changing Looks

Adorable in polka dots, the N.Y.C.-born brunette sunned herself on a pool float.

As a senior at the Pine Crest School in Florida, Frankel hosted a luau in a fuchsia lei and matching lipstick. "And I had those caterpillar eyebrows," she jokes. As for her very '80s mane? "Basically, the bigger the better. I had a total afro in high school."

As a The Apprentice: Martha Stewart finalist, the BethennyBakes doyenne began to doll up for her red-carpet appearances. "I used to go to the Bloomingdale's Trish McEvoy counter to get my makeup done," she says. "Also, I went to The Russians, this place right next to my building where everyone is Russian, for my blowouts."

For an Oscars party, she tried out bold pink lipstick. "It looks like what I wore in high school," Frankel, her own worst critic, says. "It's a little cheesy."

She kept her look understated for a Super Bowl party. "I did my own hair and makeup that night," Frankel says. "That looks like a clip [in my hair], for God's sake: a total clip job. You know, this is my favorite one and I've got nothing on."

The The Real Housewives of New York City star sported lustrous waves-and a shorter cut that was not quite intentional: "This guy just decided to take four inches off of my hair without asking. Who cuts off four to six inches without asking?" Makeup artist Veronica Pastoriza complemented the retro curls with equally stunning eyes: "I did a light lid, but with lots of eyeliner, so it's fresh-faced but with some drama."

For a television event the Skinnygirl entrepreneur worked a bouffant updo. "I hate this, it looks so severe and unnatural," she says, adding, "The boobs are a story for another segment."

The bestselling author (and expectant mother) walked in the Heart Truth Red Dress Collection show rocking crimson lipstick. "I like a red lip that doesn't look severe like Snow White," she says. "I loved the color of that lip."

Frankel celebrated her new book, A Place of Yes, with a flirty sideswept 'do.

Along with expanding her Skinnygirl empire with cocktails and shapewear, Frankel launched her own talk show, Bethenny.