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The One Wardrobe Essential I Will Never Wear

I'm just not that kind of woman.

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Dressing room with a well organized closet
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I’m 47 years old, but my style aesthetic is stuck somewhere in mid-adolescence: I still wear a Swatch, dress in Gap clothes and can’t walk in heels without falling on my face. No, I don’t use a scrunchie or shampoo with Finesse and finish it off with a spritz of Aqua Net, but I still wear Chuck Taylors — with everything.

As a teen, I assumed these articles of clothing and casual footwear would fade from my wardrobe as I reached adulthood. But as the decades have passed my wardrobe hasn’t kept up.

In part, I blame my intractably teenage wardrobe on my career choices. When I entered the workforce, women were no longer lacing up Reeboks at the end of the day and tossing their pumps in the file cabinet drawer, so fortunately I wasn’t forced to spend my days in heels. This was especially true in my workplace — ranging from publishing houses to college classrooms, where business casual is the norm and which arguably also stunted my fashion sense.

The real problem, though, is I’m simply not a stiletto kind of woman. Although I do have a couple of pairs of good heels, every time I put them on I wobble like a prepubescent wearing them for the first time. I’ve never learned to steady myself, and the truth is I don’t care enough to practice. Yet I’ve held on to them, hoping that one day — despite not practicing — I’d miraculously be the woman who could make a graceful entrance in heels.

The older I get, the more I realize this is a fantasy. For instance, when I was staying at my parents’ house, I spotted a jar of Pond’s Cold Cream in the bathroom cabinet. I laughed — and even quietly judged my mom for clinging to such generational items as she herself moved into the future, until I happened to look at my wrist and was forced to realize I still had the same version of a Swatch I had originally gotten in junior high.

Oh, and I was also wearing socks with a large image of Snoopy on the ankle. It hit me at that moment: Who was I to judge when my (literally) old-school fashion habits seemed a bit more overt than my mother’s? My mother might use classic cleansing products, but she can also walk comfortably in heels. I had to face the fact that while many middle-aged adults regress emotionally to their teen selves when they return to their childhood homes, here I was, voluntarily dressing the part.   

The revelation made me embarrassed, but it also made me curious: Did other people hold on to fashion trends from their teens? I immediately asked my sister, who to my surprise revealed that she still shopped at Benetton, adding that she always seeks out the shop when she has to travel internationally for work. Then a friend confessed she uses the same hair mousse she started using in the ’80s, though (in her defense) she added that her hairstylist said it was a reliable brand. Another friend admitted to crafting and wearing friendship bracelets — and also has a friendship pin on her sneakers. Remember that ’80s trend of putting a safety pin with beads on your laces? Now in her 40s, she wears one with her son’s beaded initials.

This might be a small sample of women, but they all instantly mentioned fashion habits or products they have used since high school. To my knowledge, none of these women are wobbly in heels. But they do carry teenage fashion trends and beauty products into their 40s and 50s, and this didn’t make them wobbly in real life.

I know we shouldn’t compare ourselves with others — or at least that’s what I tell my kids multiple times a day (even if I find it impossible to practice myself). But learning about the dated fashion habits of my family and friends comforted me. It also led me to wonder whether the abilities and items I’d always associated with being a grown woman — walking in heels, applying mascara properly, amassing any amount of jewelry that didn’t come from a street fair — aren’t necessary ones for me to master. Actually, as I approach 50 I’m becoming increasingly fine with keeping my feet on the ground and outfitted in the same style Birkenstocks I had in college. These choices make me feel confident because they make me feel comfortable.