I agree clothes shopping can be 'a major pita', but I suspect with the right level of wealth and a carefree attitude, it need not be. Just overbuy things that seem right; who cares if they don't fit well or no longer seem stylish after the first wearing? And at very high-end outlets, the staff will be better at making good recommendations at a glance, you may get to know the consistent sizing/cuts, and the aura from the brand/style can cover up minor issues. (Wear something expensive confidently and it seems that's how it's supposed to fit.)