Growing up in Florida, I spent my teenage years in Roxy flip flops and colorful sundresses, dreaming of weather that required jackets, boots, and scarves. When I finally left for college in New England, I was just as excited about shopping for Fall clothes as I was about sharing a tiny room with a stranger and living in a dorm.
I saw the movie Definitely Maybe during my senior year of high school and fell in love with April’s style in the scene where she wins the cigarette bet against Will. Her look — complete with a leather jacket and knee-high boots – radiated independence and adventure, two things I desperately wanted at eighteen. I needed to add a pair of boots just like hers to my wardrobe to appropriately set the stage for this new chapter of my life.
After a summer-long search, I chose a pair of Steve Madden’s with a two-inch, not quite stiletto heel. Leaving the mall, I imagined myself wearing them as I walked through Providence’s cobblestone streets and changing autumn leaves. That 18-year-old felt like the world was at her fingertips like life was just beginning. I was going someplace new, quite literally, and these boots were going to take me there. I was ready.
The boots, it turned out, were pretty uncomfortable and not entirely my style after all (I’m actually an OTK boots kind of girl). Except for their very first outing to the dining hall and a few parties that initial semester, they sat in my closet during my college years. But when I moved to San Francisco after graduation, and then to New York City a few years later, the boots came with me. I knew I’d probably never wear them again. Now I’m positive I never will. Still, I drag them out of my closet once or twice a year to try them on to see if maybe, this time they’ll go with my outfit.
Even though they never do, seeing their reflection in the mirror reminds me how I felt walking out of the store the day I bought them — ready for anything.
Sometimes I need a little help remembering my own strength and resiliency. I think we all do.
The boots in one of their rare appearances during my college years. My freshman year roommate is on the left.
Do you have an item you’re still holding on to even though you know you’ll never wear it or use it again? Why have you kept it all these years?