I think I'm somehow Team Analytical Yet Unorganized, which seems like the worst of both worlds. I don't really have master lists or anything beyond a vague awareness of holes or things it would be nice to have, but I still shop more for items that check a bunch of boxes rather than starting with OMG-love, then working from there. What I tend to do is either realize there's something I could really use, then do an intense short-term search until I find the best option, or just randomly go shopping, but run everything through a bunch of filters before thinking about taking it home or even trying it on.
I'm discovering that some of my favorite purchases lately, though, have been things I love enough that I'll try and talk myself past my initial "Seriously?!? You think that makes sense?" reaction. I'm thinking of my drapy Anthro cardigan, for example.
For another example, I couldn't stop thinking about a cream bag for spring/summer despite knowing that it would be kind of risky for someone like me who doesn't have a great track record for keeping things pristine. So my logical side helpfully kicked in to tell me cream is the one shade that would go with all my clothes while also lightening things up enough to feel like I'm not just wearing the same fall/winter outfits all year long, which is kind of an issue with my default color palette. And then I happened to notice J. Crew had a really pretty cream bag that looks like a good size for me, with a nice, sensible cross body strap and enough inner pockets to keep track of keys/phone/etc. It also turns out it was on sale, plus there was a coupon code, meaning the price is just low enough that I won't feel too frustrated once it inevitably starts looking grungy. Long story short, that bag is now on its way to me!