I'm thinking about winter. I've tended towards jeans for a LONG time but want to try a skirt this winter. I run cold and was wondering about wearing tall boots. I've seen most outfits with booties though. I was wondering if it would be an unwise decision to purchase tall boots at this point. Thoughts?

Other factors:

I own one set of tall chocolate brown Aquatalia boots, purchased last year. They are definitely casual and go well with jeans. Maybe with the right skirt? IDK.

My calves are narrowish and it took a lot of time/effort to find boots that fit. I have a few more leads if I wanted black tall boots and maybe a bit dressier. OTOH, my lifestyle is pretty casual. OTOH, I'm hoping to create more situations where I could wear a skirt and nice boots. Since the holidays are coming, I could probably get more use if I jump now vs later.

Um, it sounds like I'm looking for enabling, but I am mostly looking for honest thoughts.