I bought these boots but I’m debating returning them because I don’t know what to wear them with. I tried them with skinny jeans but thought that looks odd. Am I supposed to roll my jeans up? Not sure I even can to be honest. Then I thought maybe with dresses to work, but maybe they’d look dumb? I am not good with fashion at all.

I was hoping to find tall brown boots since mine are falling apart, but I wasn’t having luck so I bought these hoping to be a bit more in fashion (are tall boots out?). I hate feeling like a hideous bum every day but I can’t seem to figure out how to be a pretty female. I swear my 13 year old students are light years ahead of me in this area.