I disagree with that first statement completely... "dressed to the nines" especially to do something as mundane as shopping at a mall, screams "desperate" and "afraid SAs will treat me poorly if I don't dress to the nines." Although it goes against the maxim, I always find that people look much more foolish overdressed than underdressed for any occasion, especially for a situation as commonplace as shopping.
Just yesterday on Michigan Avenue, I saw a fabulously dressed young Japanese woman. She had on killer red heels but in the back, she had stuffed them with white tissue because they were rubbing against her heels. She was just hobbling along, and these two soccer moms actually snickered at her for being vain and silly enough to wear heels like that on a freezing cold day with slippery sidewalks. There's a time and place to dress as she dressed, and it was not while shopping along a long stretch like Michigan Avenue.
And yes, there are people who are always polished and sylish. Unfortunately, most of those people don't live in the suburbs.