Sibylle’s Style Diary: Sheila Rosenblum on Living in Style From Manhattan to the Race Track

March 17, 2016 Updated: March 27, 2016

This week’s style diary is about Sheila Rosenblum, the sole owner of Lady Sheila Stable, and chief investor and manager of Lady Sheila Stable Two and Triumphant Trio, an all-female ownership syndicate. This longtime resident of Manhattan came to the world of thoroughbreds and racing after a successful career in modeling for Wilhelmina and Ford, and training as a ballet dancer as an alum of the Royal Ballet School in London and the School of American Ballet.

She encountered increasing success in the racing industry since becoming an owner in 2010. One of her horses, La Verdad, is now even part of the Millionaire Ranks pushing her earnings past the $1 million mark. She recently had the great luck to purchase American Pharoah’s half brother, which she had Triple Crown-winning jockey Victor Espinoza name ChampionoftheNile. She lives a life mostly spent between Manhattan and the horse track, always in style!

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

Sheila Rosenblum: My style is definitely something I’d call eclectic classic. Downplayed elegance with fabulous accessories, really. I’m a dress girl. I love seeing women in dresses and love it when they show some leg in a nice heel. But then I also love jeans and a shirt and blazer paired with some great boots. So the classics, really, mixed up with a twist of modern and eclectic. That really defines my personality, too, I think.


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

Ms. Rosenblum: Passionate, determined, and exuberant.

Look at your body type, be honest with yourself, and like the great Johnny Mercer once wrote: accentuate the positive!
— Sheila Rosenblum

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

Ms. Rosenblum: I suppose the different phases of my life so far have dictated the style. I was a bohemian dancer and model, then I evolved into a more refined mom and wife, and now I love getting dressed up and doing something meaningful for myself.

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

Ms. Rosenblum: Glad I only have to mention one! Back in the early 1980s, I shot a campaign for three days. They wanted someone with very blue eyes like Lynda Carter, so they booked me and I wore a Wonder Woman costume—leather boots, vinyl halter, utility belt, tiara … the whole shebang! That definitely beats the Cleopatra getup I once donned for another shoot.

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

Ms. Rosenblum: You will always find me in jeans and a blazer on any given day. And, like I said before, for the weekend, I’m very much a girl who loves dresses. With a great heel.

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

Ms. Rosenblum: This one’s easy: a great bag, great shoes, and earrings. I never go out without earrings. It’s such an easy way to elevate everything.

Ms. Eschapasse: What’s one item that makes you instantly more confident?

Ms. Rosenblum: A great pair of shoes. I forgot which actress once said that she associated shoes with a certain role she was playing. I thought, “What a concept!” I realized that I live by that same philosophy to some degree. I’ve been known to go to the races in heels and there’s absolutely NOTHING wrong with that! I love heels, and though they may not always be the conventional—or the most comfortable—it’s my thing and they empower me to do what I want to do.

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

I never go out without earrings. It’s such an easy way to elevate everything.
— Sheila Rosenblum

Ms. Rosenblum: No question: Audrey Hepburn and Jackie O. It may be cliché, but they both just hit every mark, and so effortlessly and beautifully. They have incredible taste and incredible presence. Those were two girls who definitely always wore the clothes rather than the clothes wearing them.

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

Ms. Rosenblum: Of those two, Audrey Hepburn. No one can do a cute dress and an updo like Audrey did.

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

Ms. Rosenblum: It’s really fairly simple, come to think of it: You know what looks good on you. Not focused on being trendy, but get to know your strengths and weaknesses, accentuate those strengths. I know some things will and some won’t work for me, and I rarely find a trend interesting enough to throw myself into it.

(Courtesy of Sheila Rosenblum)
(Courtesy of Sheila Rosenblum)

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. Rosenblum: A timeless Chanel jacket. It’s blue, it’s classic, it’s perfect, and I love it! It’s what you would pay a lot of money for. It’s a wonderful, well-made outfit by one of my favorite designers.

Ms. Eschapasse: And what would you never pay much money for?

Ms. Rosenblum: Trendy stuff. I would never pay much money for that … it doesn’t matter to me.

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

Ms. Rosenblum: Feminine, sexy, and chic. But I like that for anywhere I go, not just a red carpet. Wouldn’t you want to walk into the kitchen feeling feminine, sexy, and chic? [laughs] No??

Ms. Eschapasse: Which designers can achieve that?

Ms. Rosenblum: I would say Chanel, Dior, Tom Ford, Oscar de la Renta, and Elie Saab. I really like some of Mugler’s newer stuff. It’s very provocative, but in a tasteful way, which certainly catches my eye.

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. Rosenblum: Oh boy, that’s a sensitive topic around these parts! I would say, look, ladies: Look at your body type, be honest with yourself, and like the great Johnny Mercer once wrote: accentuate the positive!

Sheila’s Favorites

Favorite Color: Blue!
Favorite Perfume: Vetiver by Guerlain.
Favorite Restaurant:  Nobu, Cipriani, Le Cirque, and for lunch, Le Bilboquet.
Favorite Drink: Cabernet Sauvignon. Simple, classic, delicious.
Favorite Movie: Oh I love “The Red Shoes!” Moira Shearer was such an influence on me in that movie when I was a little girl. It’s a fabulous movie that doesn’t get enough attention, I’m afraid. Two other favorites are “Gone with the Wind” and “Breakfast at Tiffany’s,” of course!
Favorite Book: Paula McLain’s “Circling the Sun” and Gregory David Roberts’s “Shantaram.” They’re both so brilliant.
Favorite Quote: Maya Angelou truly stirred my soul when I read this quote of hers: “My mission in life is not merely to survive, but to thrive; and to do so with some passion, some humor, and some style.”

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