I completely understand where you're coming from, OP, and I don't think you're bragging 
It's tricky to dress an exaggerated hourglass. There's a reason why fashion models are very, very thin, and it's because clothes hang well on thin frames. Even plus-size models tend to be more pear-shaped than hourglass and you very rarely see a plus-size model with very large breasts, even in the Bravissimo catalogue. Large breasts are difficult to dress and they are always a problem in high fashion. Occasionally Vogue will declare that 'breasts are back' but that will be because of a model like Gisele, who is very thin with just enough boob not to be totally flat-chested. Look at Victoria Beckham, who had her implants removed when she wanted to be taken seriously by the high fashion industry. Stylists have no idea how to dress Christina Hendricks except by putting her in vintage, lingerie, or Vivienne Westwood.
So yes, it is tricky to dress hourglasses, and not every hourglass wants to look like she's on her way to a 50s theme night in a circle skirt or fitted dress.
So. If a thin frame is a blank canvas, shape-wise, which can take pretty much any combination of patterns, frills and fussy shapes, then when you are curvy you have to work from the basis that there is already a lot 'going on'. You have to stick to simpler shapes and patterns, and you have to think carefully about proportion. Wide-legged trousers and fuller skirts balance out the top half and enable you to wear a fitted top. If you're wearing a tight pencil skirt, you need a slightly looser-fitting top half. To get that slightly dressed-down look, you need clothes with a little bit of slouch in the fit but never anything too baggy - they will just hang straight down from your curves and make you look bigger than you are.