Stephanie Simons has worn many different hats throughout her 30-some years.
Her most recent? Published author, for the second time. Stephanie’s new book, All’s Fair in Love and Wardrobe: A Fashion Editor’s Rules on Shopping for Love, was officially released today. Prior to the release, we had the chance to speak with Stephanie about her process writing the book, her best dating advice and more.
Age: Early 30s
Occupation: Author/Editorial Strategist
Educational Background: BA in Communications, Saint Mary’s College of Moraga
What inspired your book All’s Fair in Love and Wardrobe?
I’d finally read The Bro Code after all of these years and thought “wow, women need one of these bibles to call their own.” Specifically, fashion-loving women. In my experience, they have the best dating stories and would best appreciate a book about “bros” and their assorted exploits. So I re-wrote Barney Stinson’s rules according to Barney’s New York, the venerable department store.
What made you decide it would be an illustrated book?
I knew it had to be illustrated before I ever wrote the manuscript. I’ve had a love affair with picture books since I was little. My grandma used to bring me a new book every time she visited (quite frequently) and we called her “book gom” (gom being my brother’s pronunciation for grandma). I remember getting so immersed in the drawings. Even now, those drawing can transport me back to a bygone time and place. I set out to find someone whose style best complemented my cheeky writing style. After pouring over hundreds of portfolios, there was no question who would be my partner.
What was the writing process like?
I have one word for you: margaritas.
In your book you combine dating and shopping. What made you sync the two?
Dating is shopping, especially in this era of Tinder. Some days you hit Bloomingdale’s—or a bar—and the temptations are so overwhelming it’s hard to make up your mind; other times it feels like all the goods have already been picked over, and horror of horrors, nothing seems to fit. All’s Fair in Love and Wardrobe encourages fashion lovers to hone their ninja shopping skills and use them to shop for love. You wouldn’t force yourself into an ill-fitting pair of skinnies, so why settle for an ill-fitting relationship? And you wouldn’t go for the fake Fendi knowing it will fall apart in two weeks—the same should apply to love, the ultimate investment.
What’s the biggest lesson you’ve learned about dating?
That every moment of your single freedom should feel like the Fourth of July and be a celebration of your independence. Because one day, after all that hope of settling down, you will. And, according to my married friends, you’ll probably wish you were single again. Now is the time to focus on yourself before you have kids and no time to shave your legs.
What’s your ideal perfect first date outfit?
I have to be honest here. It depends how attracted I am to a guy. If I’m showing leg, watch out. Dresses trump all. But I’m a ball cap and blue jeans girls most of the time.
What’s a big turn off for you when it comes to guys?
Someone so concerned with how he looks he won’t let me run my hands through his hair. That’s my thing. And I just learned that it actually has a name: cafuné. The act of running your fingers through your lover’s hair. My new favorite word.
…And, what’s a big turn on?
If he knows how to cook. H-O-T.
You have quite the resume. You went from Editor in Chief of Black Diamond Living to Fashion Editorial Manager for Piperlime. You were also on ABC’s The Bachelor. Now, you’re a published author and most recently a consulting editorial strategist for many award-winning ad agencies and global retailers. What was your first job after college?
I freelanced my way through college—as a freshman I wrote for local magazines instead of the school paper to earn extra shoe money. I was living at home and saving up knowing it would one day afford me the luxury of taking time off to write a book while everybody else was slaving away behind a desk. The summer after my freshman year I worked as an assistant editor for a weekly entertainment magazine and then went on to work on the assignment desk at Fox KTVU Channel 2 News (at one point I thought I wanted to be a television journalist, but I think having to get up at 4 a.m. quickly squashed that desire). Right after graduating, I did a stint in public relations for a couple of celebrity-themed restaurants in the Bay Area.
What have you learned through the years about chasing your dreams?
I was just asking myself this the other day. Where do I go from here? And, more importantly, how did I even get here in the first place? Sometimes I can’t even believe how motivated I am. You have to stay motivated…so, if you can’t find the will to accomplish a dream for yourself, do it for someone else. I found fuel in the passing of a friend who wanted to be a writer. So writing a book became something I had to do in my lifetime and failure wasn’t an option. I’ve been writing notes to myself for years by way of journaling. I’ve wanted to write a book since I was 19, so to be able to look back on my journals and say to my 20-year-old self “we did it!” is kind of awesome.
Do you have any other projects in the works?
There’s a third book in my brain that needs to come out. I will need a crowbar to make sure that happens.
Where do you hope to be in 10 years, in your career and in life?
Ah, I hate this question because I know that I’ll blink and the 10 years will have passed and I’ll hold myself accountable to whatever I say here. So l’ll just keep it really vague: In 10 years I hope to have mastered the art of not caring what other people think, in which case maybe I’ll run away and be a circus carnie. I do have a very impressive collection of stilettos that would classify me as a stilt walker.
Follow Stephanie on Twitter, @LoveNWardrobe.
(Feature Photos courtesy of Stephanie Simons)