Cindy Gallop’s 4 Rules of Personal Style

January 11, 2018 | Filed in: Your Closet

Our most recent Remarkable Woman, Cindy Gallop, is a lot of things, including an entrepreneur, venture capitalist, and advocate for more open attitudes around sex. But she also has a unique point of view on fashion—one that’s as bold, powerful, and unapologetic as she is. She recently shared a few rules for incorporating your personal style at work with us, including her unorthodox approach to the work uniform. 

Rule #1: Be Yourself, Professionally

When I worked in theater, I dressed very inexpensively and wore whatever I wanted. I bought all my clothes from thrift stores. Then, at some point during my first year in advertising, my wonderful boss had to take me into a conference room, close the door, sit me down, and explain in the nicest possible way that if I wanted to be taken seriously by our clients, then maybe the see-through black chiffon blouse and leopard-skin miniskirt were not the best idea. She was absolutely right to do that, and she did it in an empathetic way. And I went, “Damn, now I have to go and buy a suit.” So I went out hunting for a suit that would satisfy corporate expectations, but also wouldn’t sacrifice my creativity. I found it on the rack at a chain store in London called Whistles. It was a black-and-white houndstooth pantsuit. This is the ’80s, remember, so it had padded shoulders and a nipped-in waist. The trousers looked like ski pants. When I put it on, I looked like a million dollars. That was my first personal style lesson: You can dress appropriately for your environment and still stand out.                                                

Rule #2: Dress for Yourself

I came to New York to start up the American office of the ad agency I used to work for, Bartle Bogle Hegarty, or BBH, back in ’98. That was when Tom Ford was in his heyday at Gucci, and as I was a high-flying, highly paid advertising executive, I could afford to buy my entire wardrobe from Gucci while Tom Ford was there. I lived in their white-leather biker pants and matching jacket. When you are pitching for a client’s business, and there are 10 agencies blurring in front of the client’s eyes, being the one dressed from head to toe in white leather is as competitively distinctive as anything else.

Once, we were pitching to Sir Terence Conran, the design guru. I thought, “Oh my God, Sir Terence Conran’s coming in. What do I wear?” I went with something quite conventional, like a black top and black pants. I walked into the meeting room and shook hands with him, and he looked me up and down and said, “But they told me you’d be in white leather?” That was my second style lesson: Never dress for anybody else. Always dress for yourself.

Rule #3: Fashion Bonds People 

Everybody has their lucky outfit. My lucky outfit for summer involved a spectacular pair of genuine python-skin pants. They were a fantastic icebreaker, because I would walk into a client pitch for a meeting, and the client would go, “Oh, wow! Those pants are amazing!” And I’d go, “Thank you! Aren’t they great? They are genuine python skin.” And the client would go, “Really?” And I’d go, “Yes! Feel!” I’ve had my thighs stroked by more CEOs than you can shake a stick at. That was my third style lesson: The way you choose to dress can be remarkably effective in bonding, ice-breaking, and building relationships with clients and people you work with.                     

Rule #4: Workwear Should Make You Feel Powerful 

But the fourth lesson that I emphasize to women is the key one, because the thing about those outfits was, I was starting up an ad agency in the world’s toughest advertising marketplace.

Every morning when I put on my leather outfit, I was arming myself for battle. I was a warrior woman. My outfits gave me the confidence to go out there and do what I had to do. And so the single most important thing about your personal style is that you should wear what makes you feel great at work. Whatever you’re doing, you should wear an outfit that’s in sync with how you want to express yourself. Because that is what ultimately gets you the business results you need.

Are you ready to find a power piece of your own? We can’t promise white leather, but we can promise office-appropriate classics that will make you feel unstoppable here.