Pretty? Preposterous.

The epiphany hit me in the car on the way to the formal charity event. I was only slightly paying attention to the road as I drove, deep in thought about an impending choice: wear my new glasses and risk not being ‘pretty’, or wear them anyway so I could see everything? This was the first formal event I’d attended since the start of the pandemic, and I’d only had glasses for the past year, wearing them during work hours and driving my kids to their activities while wearing nothing fancier than a button-down shirt at best.

My default decision throughout my life has always been to look ‘pretty’, whatever that means. To make sure that my hair and my body and my makeup and the clothes and accessories I chose were somewhat in line with my particular definition of beauty, gleaned over the years by my family, friends, and chosen media: a slim woman with clear skin and dark full hair and not-too-heavy-but-definitely-there makeup, wearing clothes that always accentuated her figure. This definition has been honed over the past tens of years during my repeated fashion magazine sessions, EGOT awards show viewings, and I’m sure ads I’ve been regularly served on Instagram. Eyeglasses were not part of that definition.

This decision was nagging at me because something in the back of my mind lately has been telling me that maybe I shouldn’t care about being pretty. I am a married woman in my forties who is now much more interested in being remembered for my intelligence, humor, and loyalty than if my figure was proportionally appealing. But ingrained rules are hard to break. My guess is that many women face this choice, and only the truly confident ones intimately understand that pretty isn’t the answer. One of my fashion idols, Iris Apfel, once said that someone saved her when they told her “You’re not pretty, and you’ll never be pretty. But, it doesn’t matter. You have something much better. You have style.” Iris, and other confident women, choose what makes them feel stylish, confident, and fierce, even if that isn’t a figure-hugging fit flair dress in a jewel-toned color or a shoulder-broadening boat neck top (though both of those do look great on me). All of the others, me included, crushingly choose whatever fits their own definition of ‘pretty’.

I love how I feel wearing glasses, but didn’t think I looked pretty in them. And then I realized: who really cares? I wasn’t there to find a date, and even if I was, shouldn’t I start my night feeling fierce and confident instead of just generically pretty? As I write this it seems like a no-brainer, but at that moment in the car, my jaw dropped a bit (even though I was alone) and I felt like for the first time I truly understood what it meant to not need to be pretty.

For me, it means wearing colors other than jewel-toned ones that my mother recommended for my skin tone. It means wearing shirts tucked into high waist wide leg pants even though my stomach isn’t flat anymore. It means owning a bad hair day, as when I look at myself in the mirror I love the frizzies and irregular curls. And it means walking into that formal event rocking my trending color-blocked dress and long open wool jacket with my brown tortoise-shell glasses. I felt fierce and confident, and so much better than pretty.

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