Well, I think any of those boots could work for your style descriptors and they seem to serve different purposes to an extent. But based on the low contrast preference and the fact that you tend to like some warmer colours I would say #1 and #3...but #2 are sleek and classic and might fit with your winter wardrobe -- I just don't know because I'm not familiar enough with the contents of your closet to perform a mental "item/outfit/capsule" test in my head!
You raise a really good question, though, about the questions that guide our purchases. (Oh, I am punning this morning!)
I have to admit that I tend to shop pretty intuitively. Or at least -- if I don't get that intuitive "aha!" or "love it" about an item, I rarely bother asking myself any questions about it.
And if I do get that feeling, and I've got a wardrobe hole for that type of item, I often buy it or at least try it. (Price tag is also relevant, of course.)
But I also think I've probably internalized a lot of the questions I should be asking myself, so I'm not directly aware of them.
Before YLF, my main questions were:
1. Is this a bargain?
2. Does it fit?
3. Is it a colour that works in my wardrobe?
I didn't have a defined colour palette but I did tend to buy colours that flattered me and worked well together. So at least I had that down. And I understood about fit and almost never purchased anything that didn't fit well (or wouldn't fit well without a bit of hemming.)
After joining YLF and beginning to identify my style preferences, I stopped worrying if things were cheap, and started asking myself whether items would fit my style persona (urban prince).
Now, that question has become internalized and I rarely even look at items that don't pass that filter.
But if an item is in question and I'm unsure, here are some of my considerations:
1. Is it practical for my life and climate? There are SO many items I love that don't pass that test. It's easy to buy for my fantasy life and harder to match my style persona to my real life conditions. But it's super important to me. I'm not happy with clothes that just sit and look pretty in my closet (unless they are special occasion items only.)
2. How and where will I wear it? Do I have the necessary items to create outfits with it, or will I have to make more purchases to wear it? If so, am I okay with that? (I might be, if I want to try a new silhouette but need the supporting players to do so.)
3. Do I own something similar? How much wear does that similar thing get? Am I okay with "splitting wears" if I buy a duplicate or near duplicate? And, contrariwise, does it feel "different" enough that it will satisfy my yen for currency?
4. Can I move in it? Is it comfortable? (Clothes that are "fussy" drive me crazy and I won't wear them.)
5. Does it move my style forward?
And, if budget is in question:
6. If I buy this, what might I have to forego? What are my priorities for the season?