Thank you all for the wonderful comments everyone I'm especially happy you gals feel my style is moving the right direction for me, because I feel that too! Slowly but surely.
Lisa - Great idea, I will certainly pair the red tennies and the gingham shirt in a future outfit.
Rae - I must admit I bought both the white and denim jackets because I saw outfits that made me say "my goodness I NEED one of those!" (And fully don't regret it!) I think you could totally work a white jacket, would be especially handy to give darker outfits an instant summery lift. *enable*
Rita - This white blazer is from H&M back in May (not sure if they still have it); I sized up so it'd have a sort-of-boyfriend vibe, though it does have fitted shaping. I think it's supposed to be a semi-cropped style, but on short me it's the perfect length
Mary - I was delighted at how fun the colors in #1 turned out as well! I am formally submitting my request for a white+coral+royal purple+gold MaryK look
Louise - This is something I battle with constantly. I make sure to treat jeans as an integral part of my outfits and pair them deliberately when putting together outfits, just like I would a skirt or layering tops; this shift of thought has made a huge difference in reducing the sameness of my outfits. After that, I started to vary the cuts, washes and colors which has helped a LOT; I don't think I have any duplicate pairs using those 3 elements and I have quite a few pairs of jeans
Jonesy - Yes, the plaid dress is certainly too big; I could probably take it in 4" on both sides 0:)