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Your own barometer is all you have to go by, and often what makes a good director is knowing when not to say something. On occasions you can find yourself on a film set where the person who is wearing the director's hat is only trying to justify his position.
Matching your hat to your shoe to your bag, or your necklace to your earrings, has a tendency to look dated. Mixing up your accessories adds interest to an outfit, and can make you look much more modern and polished.
For me, there is very little difference between magic and art. To me, the ultimate act of magic is to create something from nothing: It's like when the stage magician pulls the rabbit from the hat.
In the summer I wear shorts with a bright top and ankle boots or just sandals. I'll add a nice scarf, maybe a hat, some cool sunglasses. It's all about the accessories.