Sibylle’s Style Diary: Gillian Zoe Segal on Dressing for Success

By Sibylle Eschapasse
Sibylle Eschapasse
Sibylle Eschapasse
October 2, 2015 Updated: October 25, 2015

This week’s style diary guest, Gillian Zoe Segal, is the author of the newly published “Getting There: A Book of Mentors.” The Canadian-born author and photographer has lived in New York since she was 8. Segal has met many successful people—Warren Buffett, Michael Bloomberg, among so many others—to write her newly published book, in which they share their secrets of reaching success. 

Sibylle Eschapasse: Describe your style?

Gillian Zoe Segal: I run the spectrum between simple-elegant and boho-chic.

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

Ms. Segal: Up for anything!

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

Ms. Segal: When I was a teenager I remember thinking I had to decide on a specific style and commit to it. I’d wonder, “Should I be preppy? Downtown-cool? Uptown/fancy? A hippie?” At some point I realized that I didn’t have to label or limit myself. I could just go with the flow and wear things I was attracted to. My style now is very non-deliberate. If I’m drawn to something and think it’s flattering, I wear it.

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

Ms. Segal: I recently wore a pair of red and white vinyl, over-the-knee, Wonder Woman boots out to dinner with my boyfriend. They were literally from a Wonder Woman Halloween costume—but I thought they were totally cool. One flashy accessory per outfit is enough for me, so the rest of my ensemble was pretty conservative (an A-line, black leather mini skirt and a fitted black sweater with a white skinny shirt underneath). It was a lot of fun, so don’t be surprised if you see me in those boots again!

Style involves taking risks and letting your unique personality shine through.
— Gillian Zoe Segal

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

Ms. Segal: I work from home so workdays and weekends can be one and the same, style wise. When I don’t have any meetings or social plans I am as casual as can be. I hoard jeans, have been a loyal clog wearer for years, and, call me a techie, but I also love hoodies and sneakers.

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

Ms. Segal: AG Jeans, clog boots, and … can my hair count as an accessory? The way my hair looks makes all the difference in how I feel. Left to its own devices it’s a frizzy mess, but I wish it was straight—so I blow it out to show it who’s boss. If I don’t have the time, or it’s super humid out, it’s basically up in a bun. 

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

Ms. Segal: Diane Von Furstenberg, Carolyn Bessette, and my mother, Leanor Segal. My mother has always marched to the beat of her own style drum and taught me to be both creative and resourceful. I often alter the clothing I buy (in not such small ways) and love to mix and match (old with new and expensive with thrift). Speaking of thrift, I am totally obsessed with consignment shops.

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

Ms. Segal: Style is a personal expression. If you wear exactly what everyone else wears, how they wear it, that’s not style. Style involves taking risks and letting your unique personality shine through. The best way to achieve this is to not care about what everyone else is doing and follow your heart. Don’t worry if what you wear is “in” or not. To prove that I practice what I preach, I still wear Oakley Minute sunglasses (I buy them on E-bay).

Ms. Eschapasse: What is one purchase you’re most proud of?

Ms. Segal: I get a high off of getting a great bang for my buck. A couple of years ago I bought a basic black coat from Zara and replaced its buttons with these incredible gold ones I bought at another store. So many people compliment me on it—and I tell them all what to do!

Ms. Eschapasse: What would you pay a lot of money for?

Ms. Segal: Footwear. Good quality shoes/boots really last—and can carry a classic outfit from year to year.

Ms. Eschapasse: What is most important element in dressing for success?

Ms. Segal: It’s essential to feel confident and comfortable in what you wear to work and work events. Why? We all have a limited amount of mental energy and you want to be able to focus yours on achieving your goals—not on what people think of your outfit. In order to achieve this you must know your audience and dress for the part that you want to play. A creative outfit that would go over swimmingly at your Conde Nast job might not go over so well at Goldman Sachs—and an outfit that makes you feel great at Goldman Sachs would probably make you feel super awkward at a tech startup.

Also, like it or not, people do judge books by their covers. You don’t want to have to work to get over someone’s first impression of you.

Ms. Eschapasse: Who are your favorite designers?

Ms. Segal: Missoni, Prada, Gucci, Dolce Gabana, YSL, and Theory.

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. Segal: Regarding how others dress—I certainly don’t always like what others wear, but to each her own! How boring would it be if we all dressed the same? And how would styles ever evolve? We depend on people experimenting with new things, and we all learn from each other.

With regard to developing your own style—don’t overthink it! If you like something, wear it. You never know, your friends may end up emulating you.


Favorite color: Turquoise (especially in jewelry) 

Favorite perfume: I don’t wear perfume, but when it comes to scents I love Tata Harper’s Revitalizing Body Oil. It’s like a relaxing day at a spa, in a bottle.

Favorite restaurant in NY: Mermaid Inn. Their fish tacos are the best I’ve ever had.

Favorite drink: These days it’s vodka (up with a twist). 

Favorite movie: About A Boy.”

Favorite book: The Glass Castle,” by Janette Walls.

Favorite quote: “If you never fail it means you are not trying hard enough” —Kathy Ireland (from her essay in my book, “Getting There: A Book of Mentors“).

Sibylle’s Style Diary 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