What’s Up, Sherri Shepherd? The Love, Loss Star on Playing Dress Up and Hankering for Cheyenne

Sherri Shepherd, the wisecracking co-host of the TV talkfest The View has found a new roster of ladies to chat with. The sitcom star/stand-up comedian/published author/all-around funny lady has just joined the rotating cast of the off-Broadway hit Love, Loss and What I Wore. We talked to Shepherd about performing and scored an inside view into how fashion factors in her own life.

The View has a similar format to Love, Loss…, with five women sitting and talking. Do you feel right at home?
Well, it’s different because we’re not talking back and giving opinions. I’m an actress so this gets back to my roots of living another person’s life and telling their story.

Your fashion choices are front and center on TV every day. Are you heavily involved with wardrobe selection?
Every pair of five-inch heels I wear on the show are mine. Our costume designer picks all our clothes, but half the time we end up buying them anyways because we like them so much. I didn’t think I was [into clothes] until I started working on The View. Now I’m like, ‘Ooh, that Diane von Furstenberg is to die for! Find out if we can get a discount!’

What’s the best fashion advice you’ve ever been given?
Figure out what the best parts of your body are and dress to flatter them. I love my legs and love, love, love my boobs!

What advice do you give to others?
Women of a certain age need to embrace where they are. You can’t be dressing like you’re 17 all the time. I love my legs and I love short things, but I have a five-year-old son and I don’t want to drop him off at pre-school and have people think I’m a porn star.

Can you share a personal clothing-related memory?
There’s a story in the show where I talk about a mother who died at 39. My mom died at 41 so that one means a lot to me. She loved clothes and back then everyone had big afros and bell-bottoms. I would go into her closet and try on her clothes and put her afro wigs on, which is probably why I wear wigs all the time now. My niece comes over now and we do the same thing. She’s 11 and we still play dress up.

Does your son ever join in?
He loves my wigs and will put one on in a minute. He’s not interested in my clothing, but we have a ritual when I come home. He’ll go, ‘Mommy, I want to take off your eyes’ and he pulls my fake lashes off.

There’s a segment in the show about Madonna. Do you have any fashion icons of your own?
I had the ‘Like a Virgin’ [phase]. I used to take eyeliner and melt it with my aunt’s cigarette lighter and give myself a mole. Also I used to try to do my hair like Farrah Fawcett. It never worked. I burned off all my hair with a curling iron.

The show also talks about New Yorker’s affinity for black. Do you have a favorite color of your own?
I love white. I think it says, ‘I’m confident.’ Until I moved to New York I never realized how much [New Yorkers] are into black. In LA it’s pretty much tank tops from Gap, khaki shorts and flip-flops. When I moved out here I felt like I’d never dressed up so much in my life! Even just to go out to dinner! In LA when you meet someone for dinner, you’re wearing capris and flip-flops. In New York, it’s an event.

Do you enjoy having to look more put together?
I like getting dressed up but sometimes you just want to put on a tank top and have your bra strap show…but that’s a no-go!

What drew you to this show?
I had seen the show before and loved it. They were stories I felt were talking to me. The women I’m sitting with are so funny. It’s nice to make new friends. You want to make new friends, do an [off-Broadway] play. Don't go to a club, do a play!

Would you ever consider doing a full Broadway production?
I would love to do a musical where I could be funny and talk it through because I am not Kristin Chenoweth or Capathia Jenkins! I’d do ANYTHING where I can lust after Cheyenne Jackson.