Hi Sarah!
Kudos to making the winter formula fab! You are also rising to the challenge of dressing beautifully with a casual environment and lifestyle.
1. Love that jacket! What about the sneakers in #3 with this look?
4. I adore that pink on you. Proportions are perfection, and the hat is saucy and fun.
5. Fabulous top! Have you tried a faux tuck with this. I agree that those shoes are terrific and versatile!
6. I like bootcuts on you, but I think that either the cut of the leg isn't optimal to you, or the combo of the wider leg and the longer sweater is throwing it off a bit. What about a pointier toe shoe? I'd like to see the cardi with white pants.
7. I think the black works with your coloring, and you must already know that I'm a sucker for purple. It suspect though that you'd feel "happier" in if the outfit read "arty" or "edgy." I think I know the look you're going for. Now, I love classic black, too -- Audrey Hepburn rocked this look. What about trying a couple of unabashedly black looks -- one arty and one unapologetically classic. See how you feel. Um. Now that I've typed this, I think it's high time I took my own advice!
BTW: Not sure if you've gotten a hair cut recently (Lord knows I'm overdue), but your hair is looking healthy and swingy in these photos --- with a nice movement from back to front.