You were up in the night with a baby cutting a new tooth, AND you managed the drop-off, so having clothing on is already a good look. Having clothing on that's yours, that's intended for streetwear, and that's put together? GREAT look!
Seriously, everything looks good. Here's where I think the doubts might be coming from: this kind of ensemble is a JFE look on 99.9% of anyone not paid to display clothing for a living. Wearing and enjoying JFE looks requires some mental adjustment for some of us who've put a lot of effort into figuring out what's most conventionally flattering.
The boots look good with overall proportions, to my eye.
For me personally, I'm not yet comfortable baring lower leg between cropped hem and top of boot. But it looks fine with your distressed jeans, I think? And I have big shoulders (and other things), so I don't think I'll be trying this with skinnies, because I feel like straight legs balance my torso a bit. When I tried on a top somewhat similar to yours, I liked it best with the front tucked in above a belt buckle, to at least vaguely indicate potential presence of a waist. (I don't have one.) I haven't yet posted a picture for review, so that's not a declaration of success or a suggestion.