Sibylle’s Style Diary: Philanthropist Jean Shafiroff on Helping Others, Inspiring Many, and Looking Stylish All the While

By Sibylle Eschapasse
Sibylle Eschapasse
Sibylle Eschapasse
October 23, 2015 Updated: November 3, 2015

This week’s style diary guest is the lovely philanthropist Jean Shafiroff. On the New York socialite scene, it is difficult to find one more stylish. Shafiroff is actively involved with numerous foundations and charitable causes between New York and Southampton, and takes great pleasure and pride in always looking impeccable. 

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

Ms. Shafiroff: My style varies from dramatic to simplistic. Generally, I try not to wear anything that is too boring, although sometimes the work I do requires very conservative dress.  Although I love to dress up and wear ballgowns to charity galas, I also enjoy dressing to fit into different roles.  Clearly, attending a political fundraiser requires one type of dress while attending a SoHo art party another type. Sometimes I dress like a librarian but I especially enjoy fairy-tale dressing.  It is all rather fun. 

My personality—my friends would say that I am a workaholic, passionate-in-excess, and dedicated to giving.

For me, dressing is a game.
— Jean Shafiroff

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

Ms. Shafiroff: As a teenager, I went to a Catholic high school and was required to wear a uniform. In many ways the uniform made life easier, however, I remember feeling very constricted by it. So when I was not in uniform I wore miniskirts, jeans with halter tops, or midriff-bearing blouses. I think the uniform made me want to freer and wild when I wasn’t wearing it. When in college and graduate school, I could not afford expensive designer labels but I remember wearing anything and everything that was on the trendy side. So I wore bell bottoms with platform shoes and every combination of the jean skirt.

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

Ms. Shafiroff: I think this depends on how you define wild. I define it as dress that is as completely out of line with what everyone else is wearing at a given place or event. So I suppose I’ve worn many wild things at different times.

When I was in my mid-20s and dating my soon-to-be husband, I remember wearing an outrageous shiny, pale green Lycra, body hugging Norma Kamali dress with matching fingerless Lycra gloves to a very formal French restaurant. That night Martin had told me we would be going to a club but instead he decided that we should go have a late dinner at a formal French restaurant.

My outfit was wild even for a club. When we walked into the French restaurant, seated right next to us was my very conservative superior from the Wall Street firm that I worked for. He looked at me and what I was wearing as if I had lost my mind. I was absolutely mortified and wanted to hide under the table but, of course, I could not. My crazy club scene outfit was clearly not for an old world French restaurant or for a young professional working on Wall Street. I remember when I went back to work on Monday my superior kept looking at me rather strangely. I looked away with embarrassment and could do nothing more. The dress code at the firm I worked for was grey or dark blue suits for men and woman alike. It was just expected that we would always be dressed in dark grey suits regardless of where we were.

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

Ms. Shafiroff: On weekends I love to dress casually because I need to relax. If I could wear workout clothing all day long, I would, since I love to go to exercise classes.

However, in winter I almost always wear high black boots, black tights, and some sort of skirt and blouse or casual dress outfit. Recently, I’ve started to wear more leather jackets even though leather is considered a little racy for the Upper East Side. However, all of my very young friends seem to love the leather look on me.

During the week, I am more dressed but still like to be casual during the day. At night, I love to go out and get very dressed up. For me, dressing is a game. Since I joined the Couture Council Board a few years ago, I enjoy much more dramatic dress. The Couture Council funds the Museum at FIT. I think being around all the creative students at FIT has made me look at style and fashion in a whole different light.

Jean Shafiroff in a gown by Zang Toi. (Michael Paniccia)

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

Ms. Shafiroff: I adore opera length gloves. They can make an outfit go from ordinary to fabulous. Next I love long dangling earrings for the drama they create. Finally, I love beautiful, very high pumps. The right pumps can add a great deal of glamour.

The item that makes me more confident—let’s see—yes, it is my eyeliner. I guess you could say that my signature is the modified cat eye created with dark brown eyeliner.

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

Ms. Shafiroff: If I could look and dress like anyone who ever lived, it would be Princess Grace of Monaco.  Her style and beauty were the epitome of sheer perfection.  

But probably the two women who have had the greatest influence on my dress are Audrey Hepburn and Jacqueline Kennedy. They both had tremendous style and both women were very comfortable in their own skin.  Confidence plays a big role in style. I loved their internal and external beauty. They both had a very humanitarian side.

 I think the beauty of their personalities and the value of their work influenced my desire to emulate their style.  

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

Ms. Shafiroff: Style is very different from fashion. Style first means confidence. It describes how you project yourself to the public. If you feel confident then you are going to look better. I can think of times when I might have thought that my makeup wasn’t quite right or that my hair was starting to frizz. However, I had to forget all of that and just walk into a room as if I loved the way I looked.

Style is also about taking chances. To have style you must try new looks. Some work and some do not. Style is also about breaking hard and fast fashion rules. You need to create your own unique look.

Style is not about wearing labels and the latest fashion trends. It is about mixing and matching different pieces of clothing to create an effect that works together.

For example, someone can wear a dress from H&M with a interesting vintage hat, and then add a great handbag. The key is to create a look that you want to wear and that feel good in.

It is better to repeat the same look over and over again than to wear something that doesn’t flatter you. I think we have a lot of pressure in New York to not repeat the same outfit. But that is ridiculous—I don’t think there is a designer out there that expects us to buy something and wear it only once or twice. I know that the group from Oscar de la Renta loves when I wear one of my older purchases out to a big Gala.  

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. Shafiroff: I am always proud of the one-of-a kind pieces that I purchase. Whether it is a hat from a vintage shop that cannot be duplicated or a fantastic designer piece—so long as it is unique, I probably will love it.

I would pay a lot for a great handbag that I could keep forever. This is something worth splurging on. Also a few pairs of glamorous shoes.

Next, I would pay a lot for a spectacular ball gown. I love ball gowns and even though they are not very practical, I think it is important to buy clothing I love. Ball gowns make me very happy.

If you are not willing to experiment, it can be very boring. And who wants to be boring?
— Jean Shafiroff
Jean Shafiroff
Jean Shafiroff at The Society of Memorial Sloan Kettering Gala at The Pierre hotel Spring 2015 in a gown by Victor de Souza. (Billy Farrell Agency)

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. Shafiroff: Walking down the red carpet means that I want to feel glamorous. It is the entire look that is important, but my favorite designers for the red carpet are Oscar de la Renta, Carolina Herrera, Zang Toi, B. Michael, and Victor de Souza. However, I remember getting a lot of notice for wearing a Georgina Chapman gown from J.C. Penney. 

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. Shafiroff: Many people dress well. In general, I think New Yorkers love to dress. Sometimes it is the street look that can be most intriguing.

To develop personal style I think you need to experiment and take chances. Don’t worry if it doesn’t quite work. Tomorrow you can try a new look. If you are not willing to experiment, it can be very boring. And who wants to be boring?  


Favorite color: Right now it is bright blue and hot pink, but this keeps changing.
Favorite perfume: Sisley’s Eau de Soir, but this keeps changing.
Favorite restaurant in NY: Le Cirque because of many great memories and good food. Michael’s for the lunch scene and good food—but I hardly ever go to lunch.
Favorite drink: Cosmopolitan and American red wines.
Favorite movie: There are so many—just to name two —”Clockwork Orange” and “Casablanca.”
Favorite book: Almost every book written by Dominic Dunne and Edith Wharton.
Favorite quote:“Only thing to fear is fear itself,” Franklin Delano Roosevelt inaugural address speech.
Favorite fashion quote:  “Too much good taste can be boring. … Vulgarity is a very important ingredient in life. … A little bad taste is like a splash of paprika. We all need a little splash of bad taste: It is hearty, it’s healthy, and it’s physical. I think we could all use a little more of it. No taste is what I am against.” —Diana Vreeland

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