A few weeks ago, I went to pick up my son, Jake, from school. As I approached, I noticed him sitting with his friends, and he immediately stood up, clearly uneasy about my presence. It was evident he wanted to keep me at a distance, perhaps to avoid any embarrassment. When he got closer, he quietly remarked, “Mom, why do you have to dress like that? Everyone is looking at you.”
“Not at all! They’re probably just admiring how handsome you are,” I replied.
“No, they’re staring at you. I’d prefer it if you wore something more casual,” he said, implying that my outfit was too much for his taste. I was dressed in a stylish ensemble, which I thought was perfectly acceptable.
At that moment, I decided to turn this into an opportunity for a little experiment with my teenage son. I asked if he’d like to pick out my clothes for the day, agreeing to wear whatever he chose, provided he kept an open mind and listened to my perspective about fashion and self-expression.
Jake selected a relaxed and sporty outfit for me, which I genuinely enjoyed. I often dress like this, but sometimes I prefer to elevate my look. When I asked him why he chose this particular style, he explained that it helped me “blend in” and feel less out of place. He believed that when I dressed up, I appeared as though I didn’t belong. If only he knew how many women I encountered daily who donned suits and heels—perhaps he would reconsider his viewpoint.
I took the opportunity to explain to him that no one should be judged based on their attire, not even his “embarrassing” mother. Many people choose their outfits based on comfort and personal expression, and it’s essential to focus on kindness and character rather than appearances. I emphasized that if he feels comfortable blending in, that’s great, but I want him to embrace his individuality and have the confidence to step outside of his comfort zone.
I also made it clear that a person’s clothing is not an invitation for judgment or unwanted attention. There is a respectful way to appreciate someone’s appearance without staring, especially when it comes to women. Regardless of what someone wears, they deserve respect.
Additionally, I wanted Jake to understand that being a mother doesn’t confine me to a specific style. I loved the clothes he chose for me, and I also enjoy wearing dresses, heels, and trying out trends because they reflect who I am—long before I became a parent. It’s not my intention to embarrass him; rather, I aim to be authentic. His comments about my clothing choices can be hurtful, even if they come from a place of normal teenage embarrassment.
Afterward, I shared the insights I gained from this experience with a friend, who humorously suggested that Jake would “bake these lessons into a gentleman pie.” I hope she’s right.
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Summary
The author shares an experience with her teenage son, Jake, regarding their differing perspectives on fashion and self-expression. After he expressed embarrassment over her attire, she invited him to choose her outfits, fostering a dialogue about individuality and respect for others’ choices. The discussion emphasizes the importance of self-confidence, understanding, and respect in navigating social interactions.