We love a woman who can wear pajamas out of the house, so this pick for chicest person at Milan Fashion Week, day one, is pretty self-explanatory. Stylist Ana Gimeno Brugada dressed up silky maroon pajamas with a sleek brass-buttoned blazer and a patterned scarf. The patent-leather boots, gold and gemstone rings, and sunglasses make the look elegant, not frumpy — and a stylish outfit for work.