09/16/2010 09:24 am ET Updated May 25, 2011

Taking Risks (And What I Wore)

We've all had that moment: heart in your throat, body frozen with fear, mind racing with possibilities. Should I? Shouldn't I? It's remarkable some of the choices, the risks we make as women. References to our status as "the weaker sex" are quite misleading if you think about it: when it comes to the truly tough calls in life, it usually falls to a woman to make the call.

One thing that sets us apart (among many) is our memories, especially when it comes to the fine details of taking risks and marking monumental moments in our lives. Women are quite sartorial creatures so when recalling these milestones of our lives, we can usually recall every detail down to what we wore. As part of the Jones New York Empowering Your Confidence program, I thought it might be fun to explore those memories of the moment everyday women took a leap of faith and the memorable fashion items that made the jump with them.

After years of slaving away under a particularly brutal boss, Cindy was wondering if was ever going to get out from under her horrible work situation. Tethered to her PDA all hours of the night, her marriage strained under the stress, she felt lost one day as a recruiter called her office and described her dream job with a competitor but she'd have to act fast. That also happened to be the day she'd worn her brand new suit and Italian leather heels to work as a pick-me-up. Nervous but with a newfound confidence, she agreed to do the interview that afternoon. She got the job offer on the spot and called from the street to quit. Funny enough, it's also the outfit she happened to be wearing the day she got promoted.

Dana remembers the outfit she was wearing when she decided to leave a particularly abusive relationship. As she left in the middle of the day when she knew it would be safe, she made sure to wear her favorite pair of jeans. Now happily married with two children, she says she'll never get rid of her "Freedom Jeans," which are also her "skinny jeans" that make her feel sexy when she wears them. Coincidence? Hardly.

My beloved grandmother, Frances, made the decision to go in for colon-rectal cancer surgery in July 2001. They made her disrobe into a worn cotton hospital gown but as she sat signing pre-operation paperwork, she demanded one item remain until they wheeled her in: her favorite leather frame bag stayed on her lap. I remember asking, "Grandma, do you want me to hold that for you?" and she replied, "No. A lady holds onto her purse." Upon relinquishing the bag to me, she said, "That's my good bag. You make sure nothing happens to that, now." I returned it immediately upon recovery and she's rarely switched bags since.

On September 30th, 2008 I decided to embark upon my own journey as a writer. Fifteen years in human resources and finance left many believing that I'd return, having failed. On my last day, I wore my best black pinstriped pantsuit as usual but with the addition of a brand-new ring I had purchased for the occasion. My then manager told me in my exit meeting, "I know some great recruiters when you run out of money." When I walked out of her office, I remember thinking how good it would feel that I never had to wear that suit again. I gave the suit away the next day but I wear the ring all the time. I call it my "Let Freedom Ring."

It's tough to consider taking chances in this day and age. With a skyrocketing unemployment rate, houses in foreclosure and the divorce rate climbing, it might seem easier to remain behind closed doors and keep things status quo until the weather changes. But trust me and those I've mentioned when I tell you that taking chances is magic. There's a certain heady rush when you know that this is it, the moment that can make all other moments something you may never have dreamed they could be. Whether it's your favorite pair of stilettos, a suit or the most beautiful piece of jewelry you own, mark the moment wisely. You'll remember everything about the day when you reveled in your own strength, the power of your own spirit.

Your future is calling. Dress accordingly.