If he feels like wearing something, even though none of his peers are, I want him to feel like he can. However, I want him to have the inner confidence to step out of the box if he wants. If he is comfortable dressing in a way that makes him feel like he blends in, I think that is great. I told him judging people for what they wear is very transparent, and he will be missing out on a lot in life if he is going to focus on making friends because of what they wear, what they have, or what they look like. We focus on how they make us feel, if they are kind, how they treat people. It doesn’t matter where it came from because this isn’t how we judge others. Most people wear what they are comfortable in, what makes them feel good. Regardless, I told him nobody should be judged based on how they dress - not even your very embarrassing mother.
If he only knew how many women I saw throughout the day wearing suits and heels maybe he would have a different opinion.
When I asked my son why he picked this out, he said because I “blended in and didn’t look out of place.” In his mind, when I dress up, I look like I don’t belong. Sometimes I feel like dressing up more, so I do. While I dress like this about half the time and like this look, it doesn’t always suit me.
