You hit very flattering proportions in #2 (one part light to two parts dark; search the web for more) and a nice play between naughty and demure between #1 and 2. The demure print dress plays with the same ratio --the belt, as you note-- breaks it up. The dress' empire waist (or any bust detail, for that matter) draws the viewer's eye up from the hip. Another trick is a single cardigan button fastened below the bust (consider: too conservative?). How about the print dress (no belt) with the leather jacket, both partially open and closed.
I can't quite tell from your blog photos, but I have a hunch you might want to showcase those legs (legs!). That may make shopping a challenge: hems seem to be trending down and down.
"All times of day and occasions"? For me that's denim, so I'm no help. I also don't buy into the concept of universal essentials ("Ten items no wardrobe should be without!!!"); for example, I own a tuxedo instead of a little black dress. "Dressing for yourself"? Yeah, working on it.
Best of luck. I hope you enjoy your journey.