I have always loved to shop. Clothing, shoes, bags, give it all to me! I followed all the trends and appreciated retail therapy when I needed a pick-me-up. Getting dressed in a cute outfit always made me feel better about myself. Add in a good hair day, and I was set.
But this wasn’t always the case for me. It’s never an easy time for most girls in middle school. But for me, I felt like it was extra awkward and uncomfortable. I had braces, crazy frizzy hair, a unibrow, and a nose that was a little too big for my tiny face. How could I try to be cute when I couldn’t even figure out how to tame my hair?! I also had to wear a Catholic school uniform every day, and it just hung on my petite frame, making me look like a fourth grader even though I was almost ready for high school.
When high school finally came, I had no self-confidence and resorted to flare jeans and patterned oversized sweaters when I got to throw my uniform in the dirty pile at the end of the day. Pair that with the chunky loafers and platform sneakers that were in at the time, and I was super awkward.
I knew how to create a good outfit, but it was a major fashion flop when I tried to execute the look and put it over my slouching shoulders and flat chest.
I remember looking at my sophomore yearbook photo. I was wearing a blue polo shirt with a green stripe across the front, and all I could see was my frizzy hair taking over. It reminded me of Kramer from Seinfeld, and I never forgave myself for that photo!
When I got to college in the fall of 1999, I finally started to get comfortable with myself. I started speaking up more and finally felt that I was becoming the fun person I was always meant to be. I think the kids these days call it a fashion glow-up! I even learned how to straighten my hair!
My friends and I lived in tight jeans, pointy boots, chunky necklaces, and layered tank tops. Our eyeshadow colors and earrings were always a bold statement. And when we would go out at night, our shirts were always “a going out top,” usually black, and always super tiny. I also lived in my Uggs, always had a chunky scarf with me, and I never left the house without my signature Tiffany bracelet and mini Coach bag. When I see my daughter wearing her Kendra Scott necklace, I laugh because it reminds me of my go-to bracelet.
When I graduated from graduate school and started teaching in 2005, I needed a more professional look and usually resorted to my Express brand black Editor pants and a silky blouse. I always wore a heel, even when working in first grade. On days when I was feeling preppy, I loved a classic pair of khaki pants from J. Crew or Banana Republic matched with a white collared shirt. Maybe my Catholic school days fostered my love for a button-down. This was the preppy I could stand behind, not in the way the preteens use it today!
For the whole decade of my thirties, I was either pregnant, postpartum, or nursing. My style was not a style anymore. I lived in pajama pants, leggings, and oversized tee shirts with spit up on them. When I attempted to look put together, I would throw on a long maxi dress, which was easy and comfortable but didn’t do much for my look.
At age 43, I still love keeping up with trends and fashion. Naturally, with three kids, all my extra money goes to their clothes, especially my twelve-year-old’s obsession with Lululemon and Sephora. I try to treat myself to classic pieces whenever I can.
I always have a couple of pairs of neutral sneakers that go with everything, great-fitting jeans, comfy tees (I love Abercrombie for this!), long-lasting leggings, and a great bag. I still swear by a white T-shirt!
I don’t have as much fun stuff as I used to, but I try to buy quality pieces when I can. For the cute trends, I look on Amazon for some quick, easy buys. As a preschool teacher, I opt for comfort but never look sloppy!
When I feel good about myself, whatever phase of life I am in, I am always off to a great start! And as for those embarrassing pics of all my past terrible outfits, it was part of my journey and got me to where I am today!
