Style for me is much more a feeling than a look. Although I absolutely love the look of my style; it is the feeling that it conveys to my soul that is most meaningful.
I first became aware of that “feeling” as a little girl but then it was a bad feeling. Oh how I dreaded putting on a dress. The anguish from the discomfort percolated in my stomach. I anxiously awaited that moment when I could rip off the dress and be myself again. Although I don’t have an independent recollection,I apparently expressed this hatred for dresses when I was very young. Thankfully, my parents accommodated me BUT there were occasions where dresses just had to be worn. Ugh!
I was a classic tomboy—I dragged on my shorts, jeans, t-shirts and tank tops and was always on the move. I have wonderful memories of growing up in Kingston, in a beautiful suburban neighborhood called “Hope Pastures.” The children played outside safely without parents hovering. I was always outside with the boys till the street lights appeared and my mom warmly but loudly called for me to come inside. I played football with the boys,rode my bike with my dog, Hunter, chasing behind me, ate mangoes from trees in my backyard, climbed the ackee tree till I saw distant neighborhoods, and I stood outside arms crossed body tilted listening to animated stories from an older boy that we all looked up to.
At some point, with the encouragement of my Mom, who was tired of the struggle of combing out my long thick hair, I got my very first haircut. I went from being a pretty little tomboy with long hair to looking like a handsome little boy. I was only about 10 years old and didn’t expect it but thoroughly enjoyed when people thought I was a boy. Sometimes I corrected people and sometimes I didn’t. Just like I do now, many decades later, I felt like myself when I presented very masculine.
My neighborhood completely accepted and embraced me as a tomboy. No one challenged my lack of conformity with my gender. However, my elementary school was not accepting at all. All girls were required to do ballet, which was just as nauseating as wearing a dress. My Mom tried to have me excused from the class but we were given the choice—ballet or leave the school. So I stayed and disrupted the class or spent most of the time in the bathroom. My dad also advocated for me to join the football team and I was saddened to see how many adults were unaccepting of the concept. The culture was firm, football was for boys only—I was heartbroken.
As a teenager and adult I went back and forth with masculine and feminine clothes. I moved to New York as a teenager and later entered a profession that required suits and grew to really love that feeling of the suit. I felt like me— powerful, handsome. I made myself wear dresses and skirt suits for very special occasions. I never felt comfortable. I chuckled to myself as people excitedly complimented me and encouraged me to wear dresses more often. My closer friends chuckled with me and we laughed about how my masculine body language contradicted the dress. I sat body slanted back legs open until reminded that I need to close my legs, yikes lol.
Then finally just a few years ago, I made one of the best decisions of my life—no more wavering between masculine and feminine clothing. Ohhh man, what had I been waiting for???! I took the clean cuts from my profession and added vests, ties, bowties, oxford shirts and men’s shoes. I didn’t have a grand plan to become this dapper individual, it just came into being.
I found myself feeling intoxicated in men’s clothing stores concocting unique combinations of patterns between shirts, ties, blazers and yes, argyle socks. I relieved my closet of nearly everything feminine and graced it with dapper shirts, ties, bowties, blazers, hats and handsome shoes. I relieved myself of any and all anguish I had from presenting as a woman and graced my soul with my authentic self.
I walked into spaces where I formerly dressed like a woman presenting very masculine, bold fearless and fierce—handsome. Some people were shocked, some inspired, some curious, some attracted, regardless of the reaction of others I felt the same—phenomenal and free.