Generally off-the-rack is tough for me bacause of my short stockiness, but I have work clothes taken care of with tailor-made suits and slim-fit shirts. I want nice clothes for going out. Reserved because of my age, but I don't want to go out in business casual either. What shops should I go to? What brands? I'm leaning towards Prada or Barney's because they seem stylish and easy and they have in-house tailors. I also like the Italian look of Prada but I don't like the fashion-forward items there, I would just pick out basics. Other than this I have no idea where to start. Please help!