It’s hard to see details of the boots you’re wearing in the photos, but specific to those boots in that particular styling, I think you may be happier with a higher shaft that fits closer to the ankle for wear like this with a skirt or cropped pants. With long pants I suspect those boots look ok. But again, hard to see details of the heel style.
I’m especially enjoying sock booties for that close ankle fit, and like Kkards, I’m also all about a taller shaft these days - great with crops or skirts, so very versatile. I also have a few western styles, which are trending, but also classic enough that I’ll wear them even when not trendy. Chelsea boots and moto boot styles seem pretty timeless and more style-specific, so I wear them for years on end.
Wedges seem a little dated to me right now, but that may be my eye. These days I think not much looks truly dated — just some styles suit different wearers’ needs and personal styles better. I tend to prefer either a substantial, stompy boot or a sleek, refined, pointed toe style. Something that’s too in between feels a little wishy-washy for me. Most of my collection is below — some are 10 or more years old, while the black and white western boots and the Aquatalia black ones are new (and getting lots of wear). Clearly I prefer a block heel or something sculptural for a dressier style, and a lug sole for more casual.