Lots of people ask me how I choose a Chic Sighting - and I don't really do any choosing - they just happen! But I've devoted a lot of thought to what makes (or breaks) a Chic Sighting, and in my typically orderly fashion, I've tried to assign my observations to an alphabetic analysis.
First are foremost, you have to be appropriately dressed for your environment, both physically (the weather), and socially (no strapless dresses at rugby matches). No matter how stunning your little dress and sandals might be, if it's SNOWING and you're just wearing a dress and sandals, you are not a Chic Sighting.
Balance is an elusive concept, but the absence of balance seems to show either dubious taste, or a lack of planning. Suede boots with shorts are a common offender here. Sometimes mixing seasons in an outfit can work brilliantly - Parisiennes wearing winter sweaters over their summer dresses seemed to be effortlessly attractive - but for us mere mortals, it's a tricky maneuver.
You can also throw an outfit out of balance by trying to combine two basically incompatible moods - athletic shoes with a business suit, or a sundress with a blazer over it. This seems to happen when we try to get more mileage out of a favorite garment than is really possible. I often see women trying to wear very casual summer dresses to their office - the addition of a grey wool blazer to a pastel sundress is not going to succeed.
You've got to be comfortable - nobody limping or hobbling along in ridiculous shoes is going to be a Chic Sighting. This is not to say that you should wear sweat clothes or yoga pants everywhere - that's taking the comfort goal WAAAAAAY too far. (and I do see huge volumes of very casual clothing every day - do NOT wear your pajamas outside of your home, please) Shoes in which you can walk, undergarment straps that don't have to be constantly adjusted, and skirts that don't need incessant tugging to remain modest are all obvious disqualifiers from the concept of the Chic Sighting.