Pretty much agree with EVERYTHING the OP has said. Plus the desire to shout 'Oi, love... your bra does not fit and makes your tits look like a sock with a tangerine at the bottom. PLEASE let me help you...'
Also... Skater dresses DO NOT LOOK GOOD ON ANYONE OVER A SIZE 12. Especially if you're an apple shape.
The wide expanse of fabric over your stomach highlights it rather than creating a waist.
And Irregular Choice are not 'quirky'.
I also hate the advice to pair a 'nice' cardi or shrug with a dress (usually for a formal function). They render any wearer frumpy. Put a structured jacket on. Much better.
Ah. That's better.