What Happened When I Let My Teenage Son Dress Me

I walked into my son’s school a few weeks ago to pick him up. He was sitting with all his friends waiting for me by the door and immediately got up when he saw me coming. Clearly, he didn’t want me coming anywhere near his friends. I got the feeling he didn’t want anyone to know he was with me. I was right.

As he got closer, he whispered, “Mom, why do you have to dress like that? Everyone stares at you.”

“No they don’t. They are probably staring at you because you are so handsome,” I told him.

“I blend in. They aren’t staring at me. They are looking at you. Why do you have to wear dresses and high heels?” For the record, I was wearing the outfit below. The nerve, right?


I decided I wanted to try something with my teenage son that day. I asked him if he wanted to dress me for a little while. I told him he could pick out my outfits and I would wear whatever he wanted me to wear as long as he had an open mind and would listen to a few things I had to say about people and the way they choose to dress, so that’s what we did.

I wanted to talk to him more about the subject and why he was feeling the way he was. And by having him choose my clothes for a while I would better understand why he wanted me to wear certain things, and maybe he would understand why I like to dress the way I do and that, really, it shouldn’t affect him as much as it does.

This was his choice for the first day. He picked out a very casual, sporty outfit, and I loved it.


While I dress like this about half the time and like this look, it doesn’t always suit me. Sometimes I feel like dressing up more, so I do. 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. If he only knew how many women I saw throughout the day wearing suits and heels maybe he would have a different opinion.

Regardless, I told him nobody should be judged based on how they dress — not even your very embarrassing mother. Most people wear what they are comfortable in, what makes them feel good. It doesn’t matter where it came from because this isn’t how we judge others. We focus on how they make us feel, if they are kind, how they treat people. 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.

If he is comfortable dressing in a way that makes him feel like he blends in, I think that is great. However, I want him to have the inner confidence to step out of the box if he wants. If he feels like wearing something, even though none of his peers are, I want him to feel like he can.

I also let him know what someone puts on their body isn’t an invitation, for him or anyone else, ever. And he should always take heed on how he looks at people, especially women. There is a way to look at a woman without staring or gawking. No matter how you see her, she deserves respect. I don’t care what she’s wearing.

I also want my son to realize just because I am a mother it doesn’t mean I have to dress a certain way. I loved the outfits he picked for me, and dress like that on my own accord often. But I also love wearing dresses, heels, skinny jeans, and trying out new trends because that is who I am, and who I was long before I became his mother. It’s not my intention to embarrass him. It is my intention to be myself, and him making comments or telling me he doesn’t want to go anywhere with me because of the way I dress is hurtful (as normal as it is).

A few days ago, I discussed these “lessons” I was trying to teach him with a friend and she told me he would “take all these lessons and bake them into a gentleman pie.” I really hope she is right.