Have you ever tried Stitch Fix? I have been using it for nearly five years now, and I absolutely love it. It took my stylist (I request the same one every time) a couple of tries to really get my style and body, but now when I order a fix I keep at least two items every time! I am not easy to fit, and Rebecca gets me!
When you sign up, you will complete an extensive style profile, even linking a Pinterest board if you wish. You determine what types of items you want (or don't want...I exclude pants, accessories and shoes opting only for dresses and tops), and you set a price range for the items your stylist selects. When you schedule a fix, you pay a $20 styling fee up front and write a quick note about what you're looking for or if you have any special events coming up that you'd like your stylist to find something for. The 5 items are shipped to you then you have a couple of days to try them on and decide if you want to keep anything. The $20 styling fee comes off anything you purchase, and if you decide to keep all five items, you'll get 25% off your fix.
My latest fix was perfect, and I opted to keep three of the five items: a super cute dress and two versatile tops.
(Sorry for the terrible photo quality!)