TIA for reading and any advice! Overwhelmed here.

I am working on filling in many (many! gaping!) holes in my wardrobe and figuring out what is really "me". I don't have an identifiable style at present. Just sort of a work uniform (that needs replacing, so trying to be more intentional and thoughtful going forward) and weekend uniform of jeans (all bootcut).

I'm just at a loss for where to begin, but around Christmas, as all these sales announcements were handily delivered to my inbox, I decided to start the process with addressing shoes! I ordered a lot of boots to try on. All have been returned, except for these two. I'm on the fence.

The black pair would be strictly for skirts/dresses. They are totally unremarkable under pants. I never wear dresses or skirts anymore, but I'd really like to. I don't because I can't figure out the footwear angle. I'm not comfortable bare-legged, but thought I could go for tights and boots. I don't yet have the dress/skirt to model the boots (or a full length mirror at home!)

The Keens are really cute (to me) and even more so in person...I think they could elevate my weekend wear a bit :). If I find the right jeans (leggings??) for tucking in....kind of unsure about the color! It's called "slate black" but it seams almost a tad olive in some lights, but overall brown-ish. What will this color go with? How would you style it?

OR....and a very real possibility because I can very oblivious to what is acceptable and could be a trend that's been over for years....are they both poor choices? Keep shopping?

Whatever I buy I want to be relevant for at least a few years. I don't need trendy, but I don't want to be a joke, either, you know?

A note...I picked mid-calf boots because I am 5' tall and read somewhere a guideline that the mid-calf would be more flattering...would not "cut in half" or some such idea. Thoughts?

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