WOW thank you everyone, I'm floored by all the wonderful responses I just want to give you all big hugs!
Sveta - The jeans in #5 are a pair of DKNYs I thrifted. When I get home from work I'll see if I can find a style name on the tag for you. They are a lot looser through the thigh than the GAP L&Ls, and have a wider fit overall but still with fitted shaping.
Denise - Thanks for writing your thoughts on #3, I will definitely try to recapture this. The black skinnies are (don't laugh!) from Zumiez (teen skater shop) and the brand is called "Empyre" cut called "Eve super skinny"; I'm not sure why they work so well on me, because my hips are no where near junior in sizing!
QM - I'm kind of surprised (but happy) you find that leaving my hair down adds style points because all I do on those days is let it air dry, and maybe scrunch some mousse in; almost feels like cheating!
Kristine - Glad you noticed the little bits of white, it's been hard to switch out of my black mindset! Our weather is still pretty gray and cool so it doesn't feel too springy yet I usually braid my hair and wear a head scarf under my helmet to keep my hair in place, but totally forgot to that day (and ate more than enough hair to remember to do it the rest of the season!).
Beth - The polka dot scarf is from Modcloth, it's this one here. Though I'm eying that Halogen one in the store, too!
Lynne - I picked up the necklace from Target a week or two ago, but I can't find it on their site I will check if they still have them next time I'm there! You are certainly right about the skinnies; even without heels they make my legs look longer and after seeing this, I'm going to try to wear them more often. Plus I just love wearing black jeans!
Ornela - YES, uncluttered is exactly what I'm going for! I still love layers and plan to don them but I definitely want the finished look to FEEL uncluttered. I think this comes from perfectly fitting clothes (working on improving this) and only lightly accessorizing. Thank you for the insightful response, it's been wonderful reading everyone's thoughts on this especially with such a broad range of analytical/emotional approaches to fashion here. I think being only half engineer-brained is a huge help because I can articulate WHY some things work, but the other half artist-brain can spontaneously form an outfit that works. And then I can figure out why later, if I want to This has always been my approach, but without having figured out what I wanted before it was just moving along too slowly and inconsistently; it's part of the reason that, as much as I love lists and planning, I just can't plan out what I'm going to wear because I do actually mood dress!