I’m another creature of habit so my favorites that actually get used near-daily naturally run out on a regular schedule. Mascara and tinted moisturizer have a regular turnover. Lipsticks I find last longer. In fact, I had a couple of lipsticks that were either too pink or too brown, that I dug out of the tubes and mixed together in little pot-style containers to make a shade that works better for me.
My blush is a cream in stick form (Milk cosmetics) and I’ve had it for maybe two years? But it looks and feels just fine so I’m using it until either that changes or I run out. I think it’s getting close to the bottom anyway.
My favorite pencil-based products (lip and eye liners, brow pencil) are regularly used and get used up enough that I don’t generally toss them until they’re down to a nub. They get sharpened to a fresh surface anyway. I don’t toss them unless the consistency changes — there’s one lesser-used pencil that has gotten chalky of late so that went.
Powder-based products last a long time. I don’t use eye shadow much, so I have some MAC shades I’ve kept for years. When I do use them, they seem perfectly fine so I’m not tossing them.
I have some old nail polishes that should probably go. I tossed a couple earlier this year because they’d gone goopy.