I used to really care what people thought. I said I didn't, but I did. I didn't like rocking the boat. While I lived differently, I did listen to the voices in this world. "Dress nicely." "Be quiet." "Don't draw attention to youself."
Lately, I stopped caring. I care about being nice to people. I care about leaving this world better than I left it. I don't care about trivial things that people may or may not judge me on, like how I look in everyday situations.
At home, I wear pajamas alot. Now, I wear pajamas in public. Not all of the time. I'll still dress up for fancy dinners or going dancing. But no one cares if I'm in jeans or PJ pants at the local coworking venue. So I just wear what I want to.
If you struggle with overly caring what people think about you, I give you this challenge. Next time you go to the grocery store, wear pajamas. You can still brush your hair or otherwise look nice. But wear pajamas.
People might look at you funny. Let them. Be okay with it. Give them a nice smile in return. The more you do this, the better it will feel.
The key to getting over social norms is practice. That's it. Just practice.
It's your life. Don't let the strangers at the store dictate what you should wear.