From my experience in working in retail (which I sincerely believe everyone should have to do at some point in their life - it seriously helps in understanding why you should ask a salesperson to get the size you're looking for and not just pull from the bottom of the pile!), I was very interested in the turnover and the movement of items over to the sales area. I became fixated (and quite frankly, still obide by) the principles of what you can wait to buy and what items will be snatched up at regular price. In a simple sum up, the staple items sell very quickly, the kitschy items will usually go unplucked and on sale.
I think we all have different pain points, as I was explaining to a colleague, in what we are willing to pay for certain pieces. For me, for some reason, I will not spend an exorbitant amount of money on outerwear! Louboutins will not be my next pump purchase in all likelihood (although I am dying for those red soles to follow me around town). I will, on the other hand, spend $800 on a suit that I will have in my wardrobe just to look at! I don't know why I do it but I do...here's one of the beauties I picked up that I just adore from Teenflo/Judith & Charles. I really love this and almost want to wait for the perfect day/meeting/event to wear this to ($425 for the jacket, $275 for the skirt - which has beautiful draping at the waistline). Until I do, it waits to be picked from the special area of my Clothing Capsule. The girls at First Canadian Place Judith & Charles are amazing and will go to the moon to help you find what you're looking for in your perfect size!
In any case, I think my money needs to be better budgeted towards better cost-per-wear items that will add to my wardrobe, which involves higher price point for outerwear!