Sibylle’s Style Diary: Cheryl Stern of ‘Shoes and Baggage’ on Being a Fashionable Shopaholic on and Off the Stage

This week’s style diary guest is award-winning Broadway actress and writer Cheryl Stern.

Cheryl is performing, in the most fashionable off-Broadway musical at the cell theatre (338 W. 23rd St., between Eighth & Ninth avenues).

“Shoes and Baggage” is a hilarious fashion-forward one-woman musical about the high of the buy. It’s a musical she wrote herself about the insatiable urge to purchase and possess beautiful things, and the deeper feelings that propel this behavior. This Broadway veteran takes us on a wild, hilarious, and heartbreaking ride of hunting and spending as she digs deep to understand her own obsession with shopping. 

From her escapades in the cast of the star-studded Broadway revival of “The Women” to her stint as coach and host on The Home Shopping Network, Cheryl portrays over two dozen characters, illuminating the secret yet relatable world of retail enslavement. From Chanel, Prada, and Dior, to being a shopaholic in this show, Cheryl Stern shares with us her perspective on style as a woman who certainly loves to shop!

Sibylle Eschapasse: Describe your style?

Cheryl Stern: My style has evolved over the years but has always included a mix of trends and what suits my body. I’m five feet tall so I love pieces that are simple, yet fun and unique. I love sheath dresses, skinny pants, high-low tops with one great piece of jewelry, and a great pump or pointy flat. Sneakers are my thing this spring. Comfort is winning out these days, and they are so cool right now!!

Ms. Eschapasse: If a close friend were to describe your personality in three words, what would they be?

Ms. Stern: Bright, intense, and loving.

Ms. Eschapasse: How did your style evolve since you were a teenager?

Ms. Stern: I used to be obsessed with what was of-the-moment even if it didn’t suit my body type. I think I have come to terms with who I am and enjoy wearing what flatters me most, regardless of trend.

Ms. Eschapasse: What is the wildest thing you ever wore?

Ms. Stern: A full-on green Spandex snake suit with long red finger nail/claws and five-inch, bedazzled heels on Broadway!!

Ms. Eschapasse: How do you dress on workdays versus weekends?

Ms. Stern: Weekends are often work days for me. Rehearsal clothes are usually leggings and a chic top with ballet flats. I love to dress up after a show to go out for a drink or late dinner. That’s when the heels and a fun dress come out.

Ms. Eschapasse: What are three accessories you can’t live without, and what’s one item that makes you instantly more confident?

Ms. Stern: I always need a great bag, a great shoe, and watch! Heels make me confident because I feel taller and longer and thinner!

Ms. Eschapasse: Who have been your greatest fashion influences? 

Ms. Stern: Coco Chanel, Audrey Hepburn, Ellen Barkin, Sarah Jessica Parker,  Mary Tyler Moore as Laura Petrie on “The Dick Van Dyke Show”!

Ms. Eschapasse: Who is your style icon?

Ms. Stern: Elaine Stritch! Because she just wore a white shirt and tights. Iconic! Simple and bold.

Ms. Eschapasse: What does having style mean to you? In other words, please define style.

Ms. Stern: Having style means knowing who you are and how to adorn with flare and ease. Knowing how to take what’s classic, what’s new, and what’s unique, and mix them effortlessly to create a look that is totally your own.

Ms. Eschapasse: What is one purchase you’re most proud of? What would you pay a lot of money for, and what would you never pay much money for?

Ms. Stern: I love my Cartier watch! Never goes out of style and so chic with everything. I never change watches unless for formal events. I will invest in good handbags and good shoes and a good jacket, but hate spending too much on trendy clothes.

Ms. Eschapasse: When you go on the red carpet, how do you want your outfit to make you feel? Which designers can achieve that?

Ms. Stern: I want to shine! I want the dress to make me feel slim and free and happy and elegant. I hate constricted or corseted gowns. I want to feel at ease and alive. A clean line in a great color. I have thin, long legs so I like to feature them. Long dresses don’t do much for me and always make me feel dowdy and short. Alvin Valley designed a gorgeous opening night dress for me and I talk about it in my show, “Shoes and Baggage”!

Ms. Eschapasse: What do you think of how others dress and what’s your advice to people who would like to develop their personal style?

Ms. Stern: I think about this a lot. Personal style has to come from confidence and self knowledge. If you understand who you are and own that, then I think your style can emerge freely. What we wear says everything about who we want to be and how we see ourselves in the world. I think it’s important as we age to know what works. The heels can be a little lower and you use less heavy makeup and trendy stuff. Keep it simple and elegant and fun at the same time. A little whimsy goes a long way. Working too hard to look 20 at 50 is just not pretty. Let the super minis and sky high platforms go and move on!!

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Cheryl’s Favorites

Favorite color: Blue! Lots of blue and turquoise. I have blue eyes and my mother started dressing me in blue from day one, and it has stuck.
Favorite perfume: Jo Malone’s Lime Basil Mandarin
Favorite restaurant in NY: Pearl Oyster Bar
Favorite drink: Vodka Martini
Favorite movie: “Baby Boom”
Favorite book: “Time and Again”
Favorite quote: Don’t work harder, work smarter!

Sibylle’s “Style Diary” is a column that explores style from the perspective of choices, and what that means for different people, with personal advice from some of the most stylish people in New York.

Sibylle Eschapasse is from Paris and now lives in Manhattan. She is a journalist and a contributing writer to various publications. Sibylle is also the author of a children’s book, “Argy Boy a New York Dog Tale.” She may be reached at sibylle.eschapasse@gmail.com