Lots of very interesting replies! I guess we all have things we're built for, and things we're not.
Jude, thanks for the suggestion. I can wear delicate heels -- and I love t-straps! I have two pairs. I can't do delicate flat very easily, though.
Angie -- I wonder if it really is proportions at play - or simply your sartorial preference? You seem petite and small boned from your pics. Dainty footwear should suit your frame. It really is proportions, I'm sure of it. I am indeed petite and small-boned, and dainty heels look just great. It's the flats that are tricky. I don't have typical IT shoulders, but they're very square, and I have enough boobage that it's easy for them to prop up tops so that they "fill in" the sharp angles of my shoulders and make my upper half look blocky. Combine that with narrow hips, and it makes me look very top-heavy. And for some reason flat dainty shoes exaggerate the effect, whereas dainty heels do not. (It is true, however, that I tend to gravitate to tougher-looking footwear. But I like sleek sometimes too! And those cutout Fluevogs are gorgeous...I wanted them too).
Janet, lol@ the "shift" comment. I'd probably "look like shift" in a shift, too.
Beth Ann, lol@"boho makes me look like a worn-out hippie". I'd argue that that is a general risk when undertaking the boho look -- I mean, even the Olsen twins looked like worn-out hippies (or batty bag ladies) half the time, and they were about twenty when they started dressing like that!
Suz, just about every pair of dressy shoes I own have some kind of strap. The only ones I have that are low vamp are tight enough that they don't slip -- but I had to buy them too tight and have the toe box severely stretched out!
Kiwigal, shirts are a battle for just about all of us, I think.
Gaylene, let's see a picture of you in your tuxedo and lace!