The worst compliment, in my eyes, isn't "bubbly." It isn't even the auspicious "such a character." The most backhanded, undermining and secretly mean thing you can say to somebody is to describe their sartorial choices as "flattering." Not only is this a boring waste of words, but it also very much subtly implies that something about the person you're offering probably unsolicited comment on needs said flattery; that without flattery this person is rendered in some way unacceptable.
And, not to turn this into a feminist issue (just kidding), you never, ever hear the word flattering in relation to a boy. Never are they applauded for covering up a balding head or concealing a could-be-pregnancy belly. So why are we so very used to hearing it in terms of the girls and their constantly perceived and pointed-out flaws? It's annoying, unfair and turns clothes and makeup into a stressful, never-ending game of fixing - and it needs to stop.
To waste ones aesthetic choices entirely on trying to make oneself look better (read: more acceptable) is a borderline tragedy. If everyone is trying to "flatter" themselves into the same standardized image of attractiveness, everyone is molding themselves into the same bland abstraction of femaleness. And worse, no one is trying out things for fun, or to be different, or just to see what it looks like. A culture of fear-of-mistakes settles around how people dress or do their makeup, and that's a sad thing.
Because, let's be honest, a lot of what I do to myself isn't what other people would think of as a "flattering" choice. I've been cultivating a uni-brow for the past year, and just recently taken to clipping my fringe into a center parting like a caricature of a nerd. I'm not interested in "flattering" my apparently problematic face and body, I don't want to fix my imperfections and distract from my flaws. There is and should be an element of subjectivity here. One man's "flattering" is another man's "good God, what on earth is that?" That's a good thing. And I'd rather elicit the "good God" response than the pernicious "flattering" any day.
So next time you sense some anxiety seeping into your getting-ready routine, take a moment. You pretty much look how you look, and there's no point fearing that you've not adequately disguised your "problems". Your problems aren't problematic, they just exist. Instead of thinking about them, think about that exciting new metallic lipstick or those gloriously ugly shoes. By wearing something deliberately a bit off-key, the rest of you will look much more aesthetically pleasing in comparison. Now that's the kind of flattering I can get on board with.