I rather strongly try to avoid doing that sort of thing. I have a habit of having an outfit that works very well for some specific context and buying something

I rather strongly try to avoid doing that sort of thing. I have a habit of having an outfit that works very well for some specific context and buying something similar to it repeatedly. But outside of things I wear to work every day, I don't really need that many context-specific outfits. I don't need 7 dresses that are perfect for summer weddings (even if they're cute). I don't need 7 things to wear to the holiday party. I don't need 7 outfits to wear to the gym - even if they're sometimes athleisure. Quite often I very directly say to myself, "no, I can't get this, I already have it" - even if the thing I have is its functional equivalent, and not a duplicate. There's no value to having two perfect things to wear to the same event. There are a tiny handful of mainstays I'd be happy with 20 perfect copies of (socks, mainly). Otherwise I'm trying to match the context and venue, and assuming that is unforeseen, I need a diverse closet to match. To take your example, why not just get 2 or 3 and run them into the ground? I feel like even worn every other day jeans should last several years... and how many venues do you really wear jeans to?