First off, may I say (as another northern living person who wears a lot of jeans and trousers) I am astonished at the economy of your bootie wardrobe?
Compare to me, with my supposedly "moderate" closet -- I currently own -- count them -- (gulp) -- no fewer than 6 pairs of booties.
1. Black almond toe Stuart Weitzman chelsea bootie (2 inch heel)
2. Ink blue Zara pointed toe neoprene top bootie. (2 inch heel)
3. Munro cranberry suede bootie.
4. SE Petty snakeskin almond toe flat bootie.
5. Light taupe suede Report "Marant" type bootie.
6. Cream flat pointed toe bootie.
I also own a pair of "shooties."
Oh, and this does not count true BOOTS -- my Blundstones, while bootie height, I place in that category.
Admittedly, some of my booties are rather old. And I make up for my abundance of booties with a serious lack of actual shoes.
But I mean, really -- in our climate -- you need booties for different purposes. Casual ones and dressy ones. I'm actually considering adding a few myself and while I might subtract the Reports (as a bit dated) and possibly the Pettys, I know I'll still be wearing the heck out of all the others.
Now, onto you. The first boots look great, but quite casual.
My Zara ink booties are similar in shape/ style to the first Topshop booties. It's a super versatile option that works across formality levels and can be worn with pants and dresses.
Love the others, too. But I have no idea about Topshop comfort. I would expect it's a bit like Zara -- totally hit and miss, with most being a miss.