It's not as though I own any Chanel or LV, but even if I did I probably wouldn't spend any arms or legs on clothes. At least not now. I'm in the process of losing weight, and that means I refuse to invest too much money on clothes I will eventually not be able to fit (yay). I will only buy new clothes when I notice my current ones are getting just too shabby (happening now, ugh), and I'll try to get the best deal I can.
That said, I am really honestly over shopping at places like JCP for clothes. I've shopped there almost exclusively and well, all my clothes are basically shabby. So, yeah. I'd like to branch into those mid-range brands like Banana Republic, Zara, etc, but still only when I've gotten down to a lower weight (and tbh, when I learn to take better care of my clothes. I should probably be doing more than just washing and drying them...).
I will totally save up/invest in a good bag, though, because like someone else said I don't have to be a specific size to wear it, and I'll be able to get way more use out of a pricey leather bag than a $20 fabric/pleather bag. It'll also force me to really consider what I'm buying, and whether or not I'll still want it in my life 5, 10 or even 20 years from the day I buy it. I'm not spending big bucks on something I couldn't see myself carrying for more than a year, or a season.