When you’ve worn jeans all your life

[OntheWaves40]

I live in high waist jeans and fat face type hoodies.
I keep buying random knee length dresses that I never wear.
I want to move away from wearing jeans 24/7 but what would you start with?
For context, I’m tall and overweight.

A dress, but not random.

You don't say what size you are ...

I'd suggest

Jumpsuits.
Denim dresses / skirts.
Trousers / tailored shorts of the most flattering length.