A few weeks ago, I strolled into my son’s school to pick him up. As I approached, I noticed him sitting with his friends, and he immediately stood up, clearly trying to distance himself from me. It was obvious he didn’t want anyone to know he was associated with me.
As he came closer, he leaned in and whispered, “Mom, why do you have to dress like that? Everyone is looking at you.”
I chuckled and replied, “No one is staring at me; they’re probably admiring your good looks.”
He shot back, “I blend in. They’re looking at you. Why do you wear dresses and high heels?” For context, I was dressed in a perfectly acceptable outfit, but I could feel the judgment.
That moment sparked an idea in me. I suggested that he pick out my clothes for a day, and I would wear whatever he chose, provided he kept an open mind. This would allow me to understand his perspective while also sharing my thoughts on personal expression through fashion.
On our first day of this little experiment, he selected a very casual and sporty ensemble, which I surprisingly enjoyed. Although I wear casual attire half the time, I also love dressing up. When I asked him why he preferred this outfit, he explained that it helped me “blend in” and not stand out. In his eyes, when I dressed up, it made me look out of place. If only he realized how many women confidently wear suits and heels daily, perhaps his view would shift.
I took that moment to stress an important lesson: no one should be judged based on their clothing choices—not even the “embarrassing” mom. Most people wear what makes them feel comfortable and happy. I emphasized that we shouldn’t evaluate others based on superficial traits like clothing; rather, we should focus on kindness and how people treat each other. I told him that if he limited his friendships based on attire, he would miss out on meaningful connections.
While I appreciate that he prefers a style that helps him blend in, I want him to develop the confidence to express himself freely. If he has a desire to wear something outside the norm, I want him to feel empowered to do so.
Additionally, I made sure to tell him that someone’s outfit is never an invitation for anyone to objectify them. He needs to be respectful, particularly towards women, and understand that there’s a way to appreciate someone without staring.
I also pointed out that just because I’m a mom doesn’t mean I have to conform to a specific style. I genuinely enjoyed the outfits he picked for me, and I often wear similar clothing on my own. However, I also embrace dresses, heels, and skinny jeans because they reflect who I am—something I was long before becoming his mother. While his comments about my appearance can be hurtful, I remind myself that it’s all part of the teenage journey.
Recently, I shared these lessons with a friend, who humorously suggested that he would “bake all these lessons into a gentleman pie.” Let’s hope she’s onto something!
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Summary
In this reflective piece, I share my experience of allowing my teenage son to choose my outfits for a day, exploring the lessons about self-expression, judgment, and respect that emerged from this unique interaction. Our discussion allowed me to understand his perspective on fashion while emphasizing the importance of confidence and kindness above outward appearance.
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