Interesting reading, Carla and many commenters.
As for myself, I actually don't feel I have taken any sartorial risks. I usually don't see view wardrobe items as risky, unless they are worn in a completely strange setting, like sporting a swimsuit as office wear or wearing stilettos in deep snow, which I have never felt the slightest temptation to do.
But I do know that up through the years, others have viewed some of my choices as rather courageous--like insisting on going grey when "all others" indulged in dying, or wearing midis when few others did so, or sporting bold, colourful glasses that noone around me dared to wear.