Rainbow Belts & Cowgirl Boots: A Journey to my Personal Style
By Lucy Flood
Recently, I started working for a start-up where the entire team is seriously stylish. The CEO often wears a large blue lapis gold ring on his left hand and another flower-patterned copper ring on his right. Around his neck hang roughly five bead necklaces and sometimes an intricately patterned Indian scarf. Hip sneakers adorn his feet. Don’t get me started on the gorgeous bags he carries to work.
Sure, his outfits might sound eccentric, but on him, they work incredibly well. So well, in fact, that when he recently visited India, people took him for a Bollywood star. Yet he’s just one of many of my team members who have cultivated their own unique brands of style.
In the presence of so much devotion to clothing and appearance, I noticed that I felt insecure, even in outfits that normally made me feel attractive. I worried that because I wasn’t dressing as thoughtfully, I wasn’t being fully valued by my co-workers.
PLUS, I WANTED TO DISCOVER WHAT THEY KNEW FOR THEMSELVES—HOW TO DRESS IN WAYS THAT ARE MORE CONGRUENT WITH THE MANY FACETS OF ME.
That’s when I reached out to Sara Webb Hiris, my former Stanford roommate, who runs a style consulting business focused around women, empowerment, and life transitions. Part of why I was drawn to work with Sara is that she wears her clothes like someone might wear art.
She began our distance consult together by asking me to snap photos of three types of clothing in my closet:
a. the clothing and accessories I loved and felt powerful and authentically me in
b. the pieces that I liked but wasn't sure how to wear
c. the items that no longer felt like me or that no longer resonated.
As I sifted through my clothes, I felt humbled and grateful as I realized how much love others had showered upon me in the form of clothing. For example, I hadn’t realized how many really beautiful pieces of clothing my mother-in-law and sisters-in-law had given me. Occasionally, I would receive boxes full of gorgeous hand-me-downs in the mail from them.
Looking at the fabulous dresses my late father had given me brought up both joy and sadness, as I remembered going clothing shopping with him and the hilarious running commentary he offered each time I stepped out of the dressing room in a new outfit. “That doesn’t do a thing for you,” he once said of a frumpy grey dress.
Or upon seeing me in a black wool coat with a ruffle running down the lapel, “That’s a knockout.” (One boutique actually jokingly asked him if he would come in one day a week to offer advice for the indecisive women who came through their doors.)
As I continued looking through my closet with Sara’s questions in mind, I also became aware of how much I enjoyed wearing a few pieces of jewelry my mother had given me, pieces that her mother and grandmother had once worn. I noticed how much I particularly loved an earring with an intricate colorful fish inlaid on it that my great grandmother had once worn, and which I had refashioned into a ring.
While looking at my clothes and doing an Artful Thinking exercise Sara uses, “See Think Wonder,” I was surprised to find that the clothes I loved best were mostly white and navy blue, incredibly well-made pieces that I hardly wore. Yet I also loved how some of the clothes in my drawers created a swirl of color.
HOW WAS I GOING TO MARRY THE COLORFUL SWIRLS AND MY LOVE OF CLEAN LINES?
Sara and I met for our first Skype meeting on a summer morning. We set aside 3 hours for our initial consult. She was poised in her office in a gorgeous scoop neck black silk top that set off her dark eyes.
I have to admit that I was feeling slightly nervous. I recalled my middle school years when after leaving a Catholic School where I had worn a uniform for six years straight, I was dropped into a school where everyone seemed to know how to match the bows in their hair with their purses and their socks. Whenever my friends offered to help me get ready for middle school dances, I felt wildly inadequate, and as though they were trying to make me over into replicates of themselves. Maybe out of insecurity, I rejected their interest in clothing as too materialistic.
All of that vulnerability began to well up inside of me as I sat in front of Sara. To my surprise, Sara began the session by leading me in a couple of mindfulness-based practices. As I relaxed, she asked me to set an intention, which she transcribed for me for later. As easily as that, she helped me connect to the part of me that was eager to discover new ways to express myself through my clothing.
Sara continued with our consult by asking me, “Can you bring out all of the clothes you love?”
“All of them?”
I stood up and collected my favorite pieces and set them behind my desk where I had Sara on Skype. To my surprise, the pile was fairly large. Then I began trying them on, adjusting my laptop screen so Sara could see each outfit.
That’s when she began showing me how I could coordinate my jewelry, shoes, and accessories to allow my outfits to pop even more. For example, I had a rainbow belt I loved, but I thought it would only work with a really over-the-top outfit, and I rarely wore such wild outfits. But Sara showed me that actually I could wear it with a lot of fairly plain or conventional outfits as a way to add some of my own personal flare. She suggested wearing a white shirt with a white tweed skirt, paired with the rainbow belt around my waist and my red polka-dotted Toms wedges on my feet.
THE OUTFIT ACTUALLY MADE ME BREAK OUT IN A GRIN. TO BE ABLE TO WEAR POLKA-DOTTED WEDGES WITH A RAINBOW-STRIPED BELT WAS BEYOND DELIGHTFUL.
The experience was so much different than anything I experienced in my middle school or high school years when friends gave me advice on clothing. Instead of trying to get me to dress how Sara dresses,
I FELT HER HELPING ME DISCOVER HOW I DRESS. FEELING SARA’S ENTHUSIASTIC RESPONSE TO MY PILE OF “FAVORITES” ALSO ALLOWED ME TO BEGIN TO SEE THAT I ACTUALLY DID HAVE A GOOD FEEL FOR MY OWN PERSONAL STYLE. As I tried on one piece of clothing after another for Sara, MY CONFIDENCE IN MY CLOTHING PREFERENCES BEGAN TO SOAR, AND THE STORY THAT I HAD NO STYLE SENSE BEGAN TO FALL AWAY.
She even taught me how to wear a gorgeous Oaxacan woven purple scarf I’d bought on my honeymoon. I loved the scarf, but because it was so long, nearly eight feet in length, I never could get it to fit well. But Sara showed me different ways to tie it and fold it so that I no longer felt swallowed up by it.
Then she convinced me to pull back out my beloved cowgirl boots. (Once, as a child, I actually begged my mother to let my brothers and me nap in our cowboy boots.) However, when I moved to California I decided they were too “Wyoming” for living in the bay area.
SLIPPING ON MY COWGIRL BOOTS FELT ODDLY LIKE RECLAIMING PART OF MYSELF. I HAD FORGOTTEN HOW MUCH I LOVED THEM.
When I pulled out a leather bag that had a flower sewn onto it, Sara said skeptically, “Your style’s becoming more refined. If that didn’t have the flower, it could work. Know what I mean?”
I looked at it, and I did see how the embroidered flower no longer went with my more sophisticated tastes. “Gotcha.”
Then she reassured me that I didn’t need to feel guilty for giving away items that no longer resonated with me, and reminded me that someone else would love them.
By the end of our first style consulting session, Sara and I were able to narrow in on a few new items I could buy to fill out my wardrobe, and Sara sent me a whole Pinterest board full of clothing she had found for me at different price points and from different brands, much of it on sale. Knowing exactly what items I want to buy makes shopping easier and more efficient.
HOWEVER, BECAUSE SARA AND I HAD CREATED AS MANY AS 100 NEW OUTFITS IN MY ALREADY EXISTING WARDROBE THROUGH COMBINING MY CLOTHING IN NEW WAYS, I have bought only a couple of new dresses and a pair of jeans.
Because Sara had told me how well made J Brand jeans are, when I spied a brand new pair at a consignment store for $40, I knew they were worth the slightly high price tag, especially since they normally go for $250.
And since our original style consult, I’ve hauled bags full of clothing down the street to Out of The Closet, the second hand store that benefits people living with H.I.V.
One amazing feature Sara offers is 30-day Style Texting, or “Stexting.” She invited me to text her anytime I had a style or shopping question during those next thirty days! I felt like I had a personal stylist with me at all times.
To top it all off, Sara finished by sending me a 14-page personalized style report that included everything from outfit compositions we had discussed from my current closet to recommended brands. It even included tips for organizing my closet, caring for my clothes, and being mindful when dressing and shopping for clothes. I go back to her report whenever I want to get re-inspired about my wardrobe.
AS I GO TO WORK OR EVEN STROLL AROUND TOWN, I FEEL SO MUCH MORE CONFIDENT AND RELAXED IN BEING ME. ONE DAY IN THE PARK BESIDE MY HOUSE A HUGE MAN STARTED SHOUTING TO ME, “YOU LOOK SO PUT TOGETHER. GOD’S GONNA LOVE YOU. HE IS.”
A few days later someone else I came across on my walk to work told me that the purple sweater I had recently pulled out from the back of my closet looked fantastic on me and that the color really worked.
To my even deeper surprise, my boss, the “Bollywood star,” started commenting on my outfits when I walked into work. “Man, the cowgirl boots are really working for you,” he said to me one morning. “I’ve got cowboy boots like that.” I smiled and told him I liked his new Vans, that I’d considered buying the exact same pair, which was true.
I remember that my father used to chat with his co-workers about their mutual love of clothing. Now I understand why he loved clothing so much and how it allowed him to connect with others. My new interest in clothing makes me feel closer to him.
There’s that well-known phrase “clothes don’t make a man.”
FOR MOST OF MY LIFE, I THOUGHT CLOTHING WAS KIND OF SUPERFICIAL, BUT NOW I SEE IT MORE AS A PERSONAL ARTISTIC EXPRESSION. EVERYWHERE I GO I SEE ART IN REGULAR PEOPLE’S CLOTHING, AND I APPRECIATE BEING ABLE TO SEE MORE OF THE WORLD. THESE DAYS I FIGURE THAT, IF I AM GOING TO WEAR CLOTHING, I MIGHT AS WELL REALLY ENJOY WHAT I’M WEARING.
I FEEL DELIGHTED THAT MY CLOTHING IS NOW A CREATIVE EXPRESSION THAT HELPS THE WORLD SEE ME FOR WHO I REALLY AM IN ALL MY LOVE, CREATIVITY, POWER, AND JOY. I FEEL SO MUCH MORE LIKE ME.
Lucy Flood has written for The Atlantic, Pulitzer Prize-winning Inside Climate News, and the Jackson Hole News and Guide. Her editing company specializes in helping writers, creative professionals and scientists write clearly, with ease, and from the heart of their inspiration. Lucy offers mindfulness-based writing trainings and retreats where she incorporates movement practices to help clarify people’s mission and message. Lucy lives with her husband in the bay area where she enjoys writing at dusk on the patio of her favorite creek-side cafe. Learn more about Lucy at LucyFlood.com.