In our family "hum-drum life" is a favorite quote for the old musical, "Singin' in the Rain." What you have, Amy, is a real life, and a full one, too!
My red jeans are rarely worn this year, too, although I wore them extensively last year, and they've faded a bit. I'm also looking for a great burgundy pair, although I do have a passable pair in my closet now. You've done a great job with the colorblocking here, and I still respond positively to the "pop" of red jeans when I see them. The color blocking and fit are terrific, as are the boots. On a side note, I've noticed men wearing red jeans recently. What about trying to pin and copy a guy's look for a little androgynous look?
As for the grey drapey top --- Everyone needs something like this in the closet. Neutral, cozy and fluid. I like it with the white underneath, and the cami idea is good, too. What about pairing it with the red jeans?
As for your feeling "blah," do you think you'd like a twinge more of structure in your casual outfits? Maybe a single accessory? I know that I like "minimal casual" looks when I use a single, but vibrant, color as a focus point. I'm not saying I look better in them, although in my case, I probably do, but I need some sort of strong element to feel the outfit is finished.
Gotta go....your post reminded me that I've not gathered the "materials" for our science experiment today..............