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Sweatpants and Stilettos

A good friend and former colleague came in to visit me at the store the other day and, as she was leaving, said something that stopped me in my tracks. I don’t think she had any idea how much her words would solidify the foundation of this company and the very philosophy which guides my life. As we were carrying her shopping bags containing her entire closet refresh for the season out to her car, she turned and remarked, “I don’t know how you do it, but you always seem to draw something out of me that not very many people get to see.”

She nailed it—my number one mission—in one sentence. I believe that every one of us was put on the planet to share something unique and meaningful with the world, and that our lives, if well lived, are an open expression of our individuality. This doesn’t mean that we are all meant to ruffle feathers or gather attention around who we are—it simply acknowledges that we all are gifted and inclined in unique ways and are, in my opinion, put here to embrace and share ourselves.

Now, in my forties, I am happier than I have ever been because I am finally living my life in alignment with this philosophy. It pains me to watch others struggling to conform in terms of how they dress, what they do for a living, who they hang out with and how they behave. I’ve journeyed through this struggle and can attest wholeheartedly to the freedom and release that ensues from getting in touch with who we truly are and fearlessly expressing it. It is our birthright to be the authors of our own lives.

How we dress and present ourselves to the world is not a superficial topic when viewed through this lens. Our wardrobe and accessories offer a meaningful opportunity to express our uniqueness. Nothing thrills me more than a styling session that concludes with a client’s getting in touch with a new or unexpressed side of themselves. I love to start every styling session by giving my client the freedom to select a few of their favorite pieces. Much of the time, their instincts guide them straight to what speaks to their heart. But, from that point forward, I often discover a human tendency to contrive what comes next based on unconscious beliefs about what they “should” be putting together. This is where I take over. My styling sessions become a client’s “play date” with themselves. We work on setting their spirit free for an hour by experimenting with the unexpected. The result is almost invariably an epiphany that cuts to the core of who they are and not just what they’ve been wearing.

My personal style is a perfect example of how what we wear can say so much about who we are. If I were to write my autobiography, I would call it “Sweatpants and Stilettos.” I thrill at the unexpected, and my passions are many and often seemingly conflicting. For me, life’s flavor is based on contrast. I am a homebody who savors quiet and privacy, yet I thrive on public speaking and performing. I vacillate between two fantasies: building a cabin in the Colorado mountains and retiring to a seaside home that overlooks a negative edge pool onto the Mediterranean. I love to burrow in my office in my writing, yet am equally energized by attending New York fashion week. And, so it follows, I would never pair sneakers with my sweatpants. It’s not remotely wrong, it’s just not me. I live for the opportunity to experiment with the unexpected. Nothing is a better expression of that than combining my two favorite things: joggers and fabulous shoes. It’s my life uniform and in its own crazy way, an expression of my very soul!

Do yourself a favor and set aside an extra 5-10 minutes tomorrow morning. As you go to get dressed for work or to drop the kids off at school, think about what your reaching for. Start by asking yourself a simple question: Do I like and feel good in what I’m putting on? If the answer is “yes,” take a moment for a little introspection. What does your style express about you? Does it give you any insight into yourself? Do you see something about yourself that you’d like to share more of with the world? Alternatively, maybe you’ll find the courage to admit to yourself that you’re dressing based on expectations versus what actually makes you feel good. If that’s the case, use this as a starting point to begin thinking about who you really are, what you’re failing to give expression to and why, and how you can bring more of yourself to the surface. You might just find that you’re a sweatpants-and-stilettos kind of gal!


Lisa Berry

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