@Oaktavia Very late to this party but yes, I too ADHD & OCD the f**k out of my jeans, for maybe 3 years now. There's such a tension between the minimalist, own fewer but better things mentality that's so deeply ingrained in much of the heritagewear community, and the fact we live within capitalism. I don't mean that as a throwaway, old commie yells at clouds statement but the brands that produce the clothes we love have to sell more to survive. And they make really cool stuff, and I want that stuff, and on and on it goes. I'm so glad I'm not really into the crazy fabrics like SDA or Samurai--though they're both absolutely gorgeous--'cause if I were I'd have a real problem lol.
I just want one all-around, wear with everything pair of jeans. I don't want to wear any other style of pant, or shorts, or multiple pairs of jeans to rotate through. Just one denim in one cut that works, and that's the quest I've been on. For better or worse, Levi's won the global fashion game and jeans go literally with everything in every context now, and I want basically what everyone's wearing just better than what everyone's wearing, or at least that's how I think about it most of the time.
But then there's so much out there and how do you know if you like something unless you try it? I was listening to Derek Guy (menswearguy) on some podcast and he told a story of someone who'd never thought about jeans until he went into a slightly higher-end store and had help finding that "perfect" pair and he walked out so happy with what was undoubtedly the best pair of jeans he'd ever had in his life, with all sorts of little details that were miles above anything he'd ever had and he'd never even thought of before.
And then he was instantly miserable because it occurred to him, thinking about all these new things, that if this pair of jeans was so good, maybe there was a more perfect pair out there somewhere for him. And that's the paradox of choice and freedom that I feel trapped in most of the time. Like, these 888s are sooooooo good, but what if the 1955 is better, for me?
How did I get "into" denim? I saw a post on r/rawdenim of a beautifully faded pair of 888s-142, worn by a woman who's name I don't know for one of the indigo invitational years, and her post said she'd done the invitational in an effort to cut down on decision fatigue because she'd been spending too much energy thinking about what to wear in the morning. And I thought: yes, I too spend too much time thinking about clothes and what to wear, and I want my jeans to look like that! I'll do what she did!
And I've spent infinitely more time thinking about clothes since that decision than I ever had before lol.
Last quick story: My dissertation advisor, an established tenured professor, wore black jeans and a black T and an indigo Levi's trucker jacket. Every. Single. Day. I was chatting with him in his office one time and somehow we started talking about student evals and he said the funniest one he ever got was a student saying he was dirty because he wore the same thing every day. He then said, completely serious: I have a closet at home with 20 of these jackets. So I guess at the end of the day ya' just gotta do what works for you and I'm not trying to end this sentence as advice but more like the broader "you" that includes me.

