What I Learned About Fashion From My Kindergartener? Care Less

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“You’re so pretty,” a security guard said, beaming down to my five-year-old daughter in a museum elevator recently. Her body visibly tightened in response, and she scrunched her face struggling to offer a feeble smile as a thank you for the compliment. For her, it wasn’t. Mentally clocking her reaction, I asked her afterwards, how the guard’s comment had made her feel? “Mom, I just didn’t like it. I’m not a delicate blossom. I don’t want to be called pretty.” I laughed at the “delicate blossom” descriptor, flabbergasted as usual as to where she picks up the particular turns-of-phrase that, as one friend puts it, makes it seem like she just stepped off a steamship. But man did I appreciate her certainty about how she wants to be viewed by others.

Style-wise (and otherwise really) she has a clarity about how she wants to present herself to the world that I certainly didn’t have at five. When I was her age, I would have been delighted if a stranger called me pretty. I dressed, or rather, was dressed—until my tween years, my mother commandeered my wardrobe—for such compliments. When I was a little girl, my mom took pride in dressing me: She had been raised by a father who was a gifted tailor, and whose commitment to an impeccable appearance was unparalleled (he cufflinked, he pocketchief-ed, he ironed everything down to his underwear) and who expected the same of his daughters.

Making sure I always looked neat and pretty was something my mom was diligent about because, in her mind, how I appeared was a direct reflection of her. Personal style was not an option. So, my clothes were carefully ironed and matching, my shoes were clean and polished, my hair (which was routinely tamed and pulled into submission) was never out of place. To this day, my mother is confounded that I go many months without ironing clothes (where is my iron anyway?) and that I deign to pair navy with black.

I’ve tried with my daughter as she has become more vocal about her wants and needs to give her the dressing leeway I didn’t have as a child; letting her steer the choice of what to wear as much as possible. This doesn’t always work. I can say the weather is a frequent culprit: explaining the necessity of a jacket in the colder months is a conversation I have too often to keep count. But sometimes, I admit, I’m the culprit too—nudging her towards outfits that I think would look good, while steamrolling her sensibility. I regret doing it every time. Her style philosophy nowadays could be summarized thusly: comfort comes first; athleisure elements must always be present; accessories (like, say, fingerless gloves) matter immensely; dressing up means adding a blazer (specifically a double-breasted one we found at a thrift store in Minnesota that reminds her of Matilda) and tie; hightops go with absolutely everything. And matching? The very concept of it eludes her.

What I’ve discovered is that my five-year-old’s joy-sparking, convention-flouting approach to dressing fits quite nicely with my mid-forties sense of self. With each passing year, I give fewer fucks about other people’s assessment of my appearance. I do what pleases me; I wear what pleases me too. And what pleases me lately has often been inspired by my daughter: ath-elements like track pants (preferably with a wider sweep at the ankle) have become something I no longer reserve simply for leisure, pairing them with crisp button-downs and Lurex knits; sneakers (New Balance and Reebok most often, though I just purchased a pair of Valsports) dominate my footwear choices; and accessories like a statement sock (the silky colorful ones by Hansel from Basel or Maria La Rosa are favorites) or a colorful beanie (I’ve been reaching for fluoro pink ones from Ryan Roche and Monoprix) have taken on a new place of prominence in my outfits.

While we often hear about how women with each passing decade experienced a sense of growing invisibility I’ve begun to feel something a bit different: perhaps because my viewfinder has shifted, I actually feel seen for the first time. Also, comfortable. My daughter pointing out that something l am wearing looks too tight or restrictive sends me right back to my closet. And, alternately, nothing gives me a more immediate boost of confidence than my daughter saying these simple words: “Mom, I really like your outfit.”

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