Sounds like you need some jeans, they last a long time and signs of wear aren't a deficit.
I used to feel that way, but giant holes in the back so everyone can see your underwear isn't a great look.
I used to patch my jeans up and they ended up looking rather unique. But I left the hippie look back when I got rid of my dreadlocks. Not sure I'd do that anymore.
I find it interesting that a lot of people here are into baggier clothing. I used to wear baggy clothing. But being tall and slim I realised that skinny fit clothing suited me better.
Ed