Fashion People Sound Off On Being (& Admiring) Rule-Breakers

Photo: Courtesy of Getty/The Daily Front Row.
Fashion is filled with creative minds that have to bend — or break — the rules on a regular basis to succeed. Designers do it season after season. Print editors do it monthly. Both rely on fresh faces — a.k.a. models that somehow push boundaries or feel novel — to visualize their ideas by wearing a zany design or posing in a delightfully absurd editorial shoot. A veritable cross section of industry rule-breakers turned out for The Daily Front Row's fourth-annual Fashion Media Awards (FMAs).

This year's honorees included Cindy Crawford's look-alike daughter, Kaia Gerber, for Breakout Model Of The Year. The award was presented by Marc Jacobs, who just cast Gerber as the face of his beauty campaign. The 15-year-old showed up with the Crawford-Gerber brood and marveled at the surreality of it all while receiving the award: "It blows my mind that last week, I was sitting in biology class, learning how to use a Bunsen burner, and here I am now." (Other FMA honorees included Tommy Hilfiger, Eva Chen, Love's Katie Grand, Harper's Bazaar's Glenda Bailey, and photographer Sebastian Faena. Presenters included Tom Ford, Carine Roitfeld, and a who's-who list of models: Gigi Hadid, Jourdan Dunn, Adriana Lima, Karlie Kloss, and Emily Ratajkowski.)

Ahead, a handful of fashion folks at the FMAs share how they've broken the rules in their careers, plus their favorite people in the industry (and beyond) that are rule-eschewing badasses. Click through for some DGAF inspiration.
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Photo: Courtesy of Getty Images/The Daily Front Row.
Sailor Brinkley Cook, Model

Who's your favorite fashion industry rule-breaker?
"Oh, man, there are so many! Rihanna, because her Fenty line is seriously amazing. And have you seen her outfits? Oh my God, she kills it. She’ll be wearing just a little slip dress and look so off-the-charts beautiful."

How do you think the rules are changing in the fashion industry?
"The industry is getting really healthy and there’s more diversity than ever. There are all different shapes and sizes appearing on the runways now. That’s always been my game plan career-wise, too. I am who I am."
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Photo: Courtesy of Getty Images/The Daily Front Row.
Eva Chen, Head Of Fashion Partnerships, Instagram

What's the biggest rule you've broken in your career?
"Choosing to take a breather between jobs when I left Teen Vogue and also when I left Lucky. It wasn’t the easiest decision for me — I’m a bit of a workaholic — but it was absolutely the best. I think recharges are necessary in any career. One thing I’ve said over and over again to college students is to slow down. Don’t be in such a rush to graduate and dive into the workforce. You have the rest of your life to work.”

Who's your favorite fashion industry rule-breaker?
"Anyone who marches to the beat of their own drum and does things their way, from young designers like [Brother Vellies'] Aurora James and Tanya Taylor, who share their POVs and ups and downs on their Instagrams; to editors like Anna Wintour who put the denim on the cover of Vogue; to models like Adwoa Aboah and Jilly Peppa, who are redefining conventional standards of beauty."
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Photo: Courtesy of Getty Images/The Daily Front Row.
Katie Grand, Editor-In-Chief, Love

What's the biggest rule you've broken in your career?
"Probably just not behaving how you should — and not caring."

Who's your favorite fashion industry rule-breaker?
"Kim Kardashian. She rewrote the rule book."

(Grand pictured, right; with Adriana Lina)
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Photo: Courtesy of Getty Images/The Daily Front Row.
Hari Nef, Model

Who's your favorite fashion industry rule-breaker?
"Alessandro Michele, because he is changing what we talk about when we talk about luxury. He’s opening certain doors and closing other doors, for good, in terms of what’s considered expensive, high-fashion, covetable, and exclusive.

How do you break the rules?
"I aspire to be a rule-breaker in the same way Alessandro is. The exclusivity of the fashion industry has manifested itself in the most boring of ways and there’s an openness in the industry is developing toward new aesthetics, new identities, and new ways of operating. The definitions of beauty and luxury are being expanded, and that's a powerful change."
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Photo: Courtesy of Getty Images/The Daily Front Row.
Ally Hilfiger, Author & Former Fashion Designer (& Tommy's Daughter)

What's the biggest rule you've broken in your career?

"The thing about fashion is that there are no rules, so I just try to do my own thing. There’s one rule in the industry I would like to break, though: delivering winter clothes to stores in July. I don’t want to buy leather jackets and sweaters in the middle of summer!"

Who's your favorite fashion industry rule-breaker?
"[Alexander] Wang. He goes to the beat of his own drum and he’s incredibly creative — he reinvents things and he’s not afraid to take risks. I really admire that.”
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Photo: Courtesy of Getty Images/The Daily Front Row.
Glenda Bailey, Editor-In-Chief, Harper's Bazaar

What's the biggest rule you've broken in your career?
"I was looking for an editor and I received an application from a woman who said she really wanted to work for me, how I was the greatest editor, and she always wanted to work on Mirabella. The only problem was that I was at Marie Claire and I never worked at Mirabella.

"Any sensible person would have put that application in the trash, but I looked at her résumé and decided to interview her. When I interviewed her and confronted her, she was so impressive with how she handled the situation that I decided to give her the job. This was many years ago and she has now worked her way on up to many other jobs, including EIC. I’m a great believer in my own instincts."

Who's your favorite fashion industry rule-breaker?
"Alber Elbaz, because he believes that treating people well, being respectful and kind with warmth and humor should be the norm; it often isn’t in the fashion industry."
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Photo: Courtesy of Getty Images/The Daily Front Row.
Herieth Paul, Model

Who's your favorite fashion industry rule-breaker?
"Adriana Lima, because she doesn’t really care about what everybody says about her and she’s breaking barriers. There’s a thing in the industry where once you hit a certain age, you can’t be a model anymore. She can do — and does do — whatever she wants."

What's the biggest rule you've broken in your career?
"Once, I went on the runway while chewing gum by accident. I can’t say which show, but it was at New York Fashion Week. You can’t tell in pictures, thankfully.”
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Photo: Courtesy of Getty Images/The Daily Front Row.
Natasha Poly, Model

Who's your favorite rule-breaker throughout history?
“Brigitte Bardot. She just has this energy of a badass — with that black eyeliner and a cigarette in her hand, she was just enjoying life and having a great time."
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