A few weeks ago, I strolled into my son’s school to pick him up, only to find him sitting with his friends. The moment he spotted me, he jumped up like I was about to announce a dance-off. It was clear he preferred I didn’t come too close to his social circle. I could sense he wanted to keep our mother-son bond undercover.
As he approached, he leaned in and whispered, “Mom, why do you have to dress like that? Everyone’s staring at you.”
“Who’s staring?” I replied, trying to sound unfazed. “They’re probably looking at you because you’re so handsome!”
“Nope! I blend in. It’s you they’re looking at. Why the dresses and high heels?” For the record, I was wearing a perfectly acceptable outfit that day—nothing scandalous!
In a moment of inspiration (or maybe a dash of madness), I proposed a little experiment. I asked him if he’d like to choose my outfits for a while. I promised to wear whatever he picked, as long as he kept an open mind. My goal was to understand his perspective on clothing choices while hopefully sharing my own insights too.
Day One of the Fashion Experiment
On our first day of this fashion experiment, he picked a super casual, sporty ensemble that I actually loved.
While I usually rock a mix of styles, I do love dressing up sometimes. When I asked why he chose this particular outfit, he said it was because I’d “blend in and not look out of place.” In his teenage mind, when I dress up, I’m basically a neon sign saying, “Look at me!” If only he knew how many women sported suits and heels around me each day; he might have thought differently.
I took the opportunity to explain that nobody should be judged based on their attire—not even their slightly embarrassing mothers. Most people wear what makes them comfortable, and that’s what truly matters. It’s about character, kindness, and how we treat each other, not the fabric we wear. I warned him that focusing on appearances would limit his experiences and friendships.
If he prefers to dress in a way that allows him to blend in, that’s totally fine. But I also want him to feel confident enough to step outside that box if he wants. It’s essential to know that what someone wears is never an invitation for anything, and he should always show respect, no matter how someone chooses to present themselves.
I also made it clear that being a mom doesn’t mean I have to fit into a specific mold. I loved the outfits he selected for me (and wear similar styles often), but I also enjoy expressing myself in dresses, heels, and the latest trends. This is who I am, long before I became a mother. His comments about my clothing can sting, even if they’re typical for a teen.
Recently, I shared my “lessons” with a friend, who hilariously said my son would “take all these lessons and bake them into a gentleman pie.” Here’s hoping she’s right!
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In summary, allowing my son to dress me not only opened a dialogue about our differing views on fashion but also helped reinforce the importance of respect and self-expression.