How Being Newly Single Skews Your Sense Of Style

It’s a funny feeling when you start to see your style change — when you open your closet door and simultaneously love and hate everything; when you slip on a favorite dress over your head and feel that familiar tug (but don’t quite want to zip up the zipper all the way). It’s an even stranger feeling when you’re starting to discover said feeling not when you’re in your underwear in front of your closet, but as you’re fidgeting with your arms crossed in a dimly lit bar.

This time a year ago, that was all me. There I was, in a speakeasy style bar filled with low hanging chandeliers and dusty Persian-looking rugs, sitting in my best Hepburn-inspired midi dress, feeling completely and totally god-awful. I’d clear my throat as I’d run a hand through my hair, quickly smiling at one of the handsome bartenders before glancing away — before not quite deciding if I should keep my hands in my lap where I could wring them, or crossed over my chest all self-conscious like. Decisions, decisions.

Before you think I’m just a really shy type of person, a little context for you: During that time, I’d been broken up with by my then-boyfriend of several years. I was newly single and figuring out how to smile at strange men again without looking like something just fell into my eye. And while our breakup was a friendly separation, one thing happened that I didn’t anticipate: I started tail spinning into an identity crisis.

You see, I had a really strong sense of style. I liked channeling my inner Lauren Bacall and Doris Day and would try to look like I was one of the girls from How to Marry a Millionaire on a daily basis. I’d wear full skirt day dresses on a normal Tuesday and long sleeve floral frocks just to go do laundry, always setting my hair in curls and dabbing my lips with red. I was happiest when I looked like I just stepped off of a 50s movie set, and I had a dress collection that would darken Betty Draper’s face with envy. It was amazing.

That is, until it wasn’t. I was never one to be shy over standing out because of my style — I mean, dresses are there to be played with. Which was why I was so perplexed over how I was feeling at that bar. I slowly spun side to side in my bar stool, fidgeting nervously. Feeling not at all attractive. And super confused over the whole thing.

My gingham dress made me feel silly in the quietly trendy bar — not classic and romantic like it always did. I felt like a little girl playing with her mother’s clothes; like I was trying on pearls and high heels when I really belonged in stretch pants and Elmo sweatshirts.

Instead of shrinking into the background like I so desperately wanted, I instead summoned all the confidence I could muster and, straightening my shoulders and calling upon my inner Katharine Hepburn, I tried to ignore the fact that I wanted a wardrobe change in the bathroom and joined my friends. Deep breaths boo, you could do this.

The day after, I tried to figure out exactly what happened. Maybe I was just feeling vulnerable because I was newly single? When you date someone for years, you become spoiled with the feeling of acceptance — that no matter what you put on and how you express yourself, you’ll still be thought of as beautiful. But as I tried to mull that over, I knew that wasn’t it. I was never one to be shy about my style; when I felt beautiful in a piece, no matter how different or out there it was, I could hold onto that sense of self. I always subscribed to the idea that fashion is about being playful and about trying to give the feelings inside you a voice, so I wasn’t one to worry about whether "this guy" or "that girl" thought my shoes were weird on the subway.

But as I considered that, I realized that was exactly it. I treated style as a way to communicate how I was on the inside. How I looked matched my voice. It matched my disposition and how I saw the world that day; it gave you a preview of who I was before we even smiled hello. So maybe what the real problem was, was that I no longer felt like Doris Day. I didn’t feel like gingham and polka dots on the inside. I felt like something... new.

The main reason my boyfriend and I broke up wasn’t really down to one particular cause. We were close friends and had this wonderful effect on each other where we’d force the other to grow and become a better person than they’d feel like being. But all that change also happened to make us outgrow each other. We were at a point where we started moving in two separate directions, to a place where we couldn’t really walk side by side anymore. So we hugged and went our separate ways.

That same change did something similar to my fur stoles and pillbox hats. While I still loved them, I just couldn’t relate to them anymore. That was an older version of myself, one I was ready to let go of.

So as I sat there in the bar, running a hand down the skirt of one of my favorite dresses, I had the wonderful chance of seeing that moment where my life paused, took a breath, and turned the page. As I ran a finger down the pleats of the skirt, I smiled. I loved this dress, but not in the same way. Just as how I was still myself, but not in the same way.

I looked up, feeling out of place and uncomfortable, but beautifully so. I raised a hand, trying to catch the bartender’s attention, and crossed my penny loafer clad feet at the ankles, knowing I’d probably never wear them again after tonight. Wishing, as I met eyes with a handsome guy two seats down before quickly looking away, that I already wasn’t.

I fidgeted again. Fought with the urge to bring a nervous hand to my throat. And smiled. Feeling so unnerved and so unsure was wonderful. Because it meant that things were about to change, and in the best ways possible.

Images: Courtesy Author/Messages on a Napkin; Giphy