I'm all about a little daring these days. Fall, with all its possibilities for layering, is the best season for sartorial experimentation. I'm using it as an excuse to break out of my high-heeled comfort zone and invest in fun flats, and to play with proportion by layering cropped, boxy sweaters with slim pencil skirts and dramatically sleek updos. It's always important to have fun with fashion, and challenge the parameters of what (you think) does or doesn't 'work' for you.